Đề tài “Tổng hợp một số dẫn xuất 7 hydroxy4methylcoumarin” gồm có 2 nội dung chính: Tổng hợp một số dẫn xuất của 7hydroxy4methylcoumarin; nghiên cứu cấu trúc của các chất tổng hợp được bằng phương pháp vật lý hiện đại như phổ hồng ngoại, phổ cộng hưởng từ hạt nhân. Mời các bạn cùng tham khảo để biết thêm các nội dung chi tiết. Đề tài Hoàn thiện công tác quản trị nhân sự tại Công ty TNHH Mộc Khải Tuyên được nghiên cứu nhằm giúp công ty TNHH Mộc Khải Tuyên làm rõ được thực trạng công tác quản trị nhân sự trong công ty như thế nào từ đó đề ra các giải pháp giúp công ty hoàn thiện công tác quản trị nhân sự tốt hơn trong thời gian tới.
BỘ GIÁO DỤC VÀ ĐÀO TẠO TRƯỜNG ĐẠI HỌC SƯ PHẠM TP.HCM KHOA HÓA HỌC KHÓA LUẬN TỐT NGHIỆP CHUYÊN NGÀNH HÓA HỮU CƠ Tên đề tài 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Tp Hồ Chí Minh, tháng - 2012 BỘ GIÁO DỤC VÀ ĐÀO TẠO TRƯỜNG ĐẠI HỌC SƯ PHẠM TP.HCM KHOA HÓA HỌC KHÓA LUẬN TỐT NGHIỆP CHUYÊN NGÀNH HÓA HỮU CƠ Tên đề tài 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc GVHD : ThS LÊ THỊ THU HƯƠNG c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 TS NGUYỄN TIẾN CÔNG 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 SVTH : NGUYỄN THỊ HỒNG THÁI 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b KHÓA : 2008 – 2012 f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Tp Hồ Chí Minh, tháng - 2012 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công MỤC LỤC MỤC LỤC .1 LỜI CẢM ƠN LỜI MỞ ĐẦU PHẦN 1: TỔNG QUAN 1.KHÁI QUÁT VỀ COUMARIN .5 PHÂN LOẠI COUMARIN .6 2.1 Coumarin đơn giản 2.2 Furanocoumarin (hay furocoumarin) 2.3 Pyranocoumarin ĐẶC ĐIỂM VỀ CẤU TRÚC 12 TÍNH CHẤT HĨA HỌC CỦA 7-HIĐROXY-4-METYLCOUMARIN (A) VÀ CÁC DẪN XUẤT .13 4.1 Phản ứng brom hóa 13 4.2 Phản ứng acyl hóa chuyển vị Fries .13 4.3 Phản ứng đóng vịng nội phân tử .14 4.5 Tác dụng với phenacyl bromua 15 4.6 Phản ứng sunfo hóa 16 4.7 Phản ứng nitro hóa 16 MỘT SỐ PHẢN ỨNG TỔNG HỢP COUMARIN VÀ DẪN XUẤT 16 5.1 Phản ứng tổng hợp Pechmann 16 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 5.2 Phản ứng tổng hợp Knoevenagel 17 5.3 Phản ứng tổng hợp Perkin [15] 17 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 5.4 Phản ứng tổng hợp khác 18 TÁC DỤNG VÀ CÔNG DỤNG 18 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 PHẦN 2: THỰC NGHIỆM 20 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 SƠ ĐỒ TỔNG HỢP 20 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e TỔNG HỢP CÁC CHẤT 21 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 2.1 Tổng hợp 7-hydroxy-4-methylcoumarin (A) 21 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 2.2 Tổng hợp 3-bromo-7-hydroxy-4-methylcoumarin (B) 22 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 2.3 Tổng hợp 3,6,8-tribromo-7-hydroxy-4-methylcoumarin (C) 22 2.4 Tổng hợp 7-hydroxy-4-methyl-8-nitrocoumarin (D) 23 SVTH: Nguyễn Thị Hồng Thái Trang Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công 2.5 Tổng hợp 7-hydroxy-4-methyl-6-nitrocoumarin (E) .24 2.6 Tổng hợp 7-methoxy-4-methyl-6-nitrocoumarin (F) 24 XÁC ĐỊNH NHIỆT ĐỘ NÓNG CHẢY VÀ CẤU TRÚC CỦA CÁC CHẤT 26 3.1 Nhiệt độ nóng chảy 26 3.2 Phổ hồng ngoại (IR) 26 3.3 Phổ cộng hưởng từ proton (1H-NMR) .26 PHẦN 3: KẾT QUẢ VÀ THẢO LUẬN .27 Tổng hợp 7-hydroxy-4-methylcoumarin (A) 27 1.1 Cơ chế phản ứng 27 1.2 Nhận xét phổ IR phổ 1H-NMR (A) 28 Tổng hợp 3-bromo-7-hydroxy-4-methylcoumarin (B) 29 2.1 Cơ chế phản ứng 29 2.2 Nhận xét phổ IR 1H-NMR (B) 29 Tổng hợp 3,6,8-tribromo-7-hydroxy-4-methylcoumarin (C) 31 3.1 Cơ chế phản ứng 31 3.2 Nhận xét phổ IR phổ 1H-NMR (C) 32 Hợp chất 7-hydroxy-4-methyl-8-nitrocoumarin (D) .34 4.1 Cơ chế phản ứng 34 4.2 Nhận xét phổ IR phổ 1H-NMR (D) 34 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a Hợp chất 7-hydroxy-4-methyl-8-nitrocoumarin (E) .36 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 5.1 Cơ chế phản ứng 36 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc 5.2 Nhận xét phổ IR phổ H-NMR (D) 36 c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6 Hợp chất 7-methoxy-4-methyl-6-nitrocoumarin (F) .37 6.1 Cơ chế phản ứng 37 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 6.2 Nhận xét phổ IR phổ 1H-NMR (F) 38 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 PHẦN 4: KẾT LUẬN VÀ ĐỀ XUẤT 41 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e TÀI LIỆU THAM KHẢO .42 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e PHỤ LỤC 44 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Cơng LỜI CẢM ƠN Trong suốt q trình học tập hồn thành luận văn tốt nghiệp, tơi nhận hướng dẫn, giúp đỡ quý báu thầy cô, anh chị, bạn bè em Với lịng kính trọng biết ơn sâu sắc, xin bày tỏ lời cảm ơn chân thành đến tất người tạo điều kiện giúp đỡ thời gian qua Trước tiên xin chân thành cảm ơn đến ThS Lê Thị Thu Hương, người cô bảo động viên để hồn thành luận văn Tơi xin bày tỏ lịng biết ơn sâu sắc đến TS Nguyễn Tiến Công, người thầy hướng dẫn tận tình đóng góp nhiều ý kiến q báu cho tơi suốt q trình nghiên cứu hoàn thành luận văn tốt nghiệp Xin chân thành cảm ơn đến Ban Giám Hiệu, Ban chủ nhiệm Khoa Hóa, phịng ban quản lý phịng thí nghiệm Hóa học Trường Đại học Sư phạm Tp.HCM Ngoài xin chân thành cảm ơn đến quý thầy cô nhà trường, người trang bị kiến thức, dạy dỗ tạo điều kiện tốt cho suốt bốn năm học đại học Cuối lời cảm ơn đến ba mẹ, em, bạn bè bên cạnh, động viên, giúp đỡ tơi lúc khó khăn học tập q trình hồn thành 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 luận văn tốt nghiệp 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b Tôi xin gửi tới tất người lời chúc sức khỏe nhất! f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công LỜI MỞ ĐẦU Cho đến nhiều dẫn xuất coumarin ứng dụng vào ngành khác ngành dược phẩm, ngành mỹ phẩm, ngành thực phẩm…[4] Một dẫn xuất quan trọng coumarin 7-hydroxy-4-methylcoumarin với hoạt tính sinh học cao ứng dụng để chống giun sán, an thần, kháng khuẩn, chống viêm, chống đông máu…[1,5] Ngoài ra, hợp chất 7-hydroxy-4-methylcoumarin dẫn xuất chúng sử dụng ngành công nghiệp hương liệu, mỹ phẩm, phụ gia thực phẩm, huỳnh quang…[4] Nghiên cứu dẫn xuất chúng để mở nhiều hướng tổng hợp dẫn xuất có hoạt tính cao hơn, hay kết hợp với hợp chất khác để làm tăng hay giảm hoạt tính tùy theo mức độ yêu cầu Theo số tài liệu [3] dẫn xuất tổng hợp từ hợp chất 7hydroxy-4-methylcoumarin thường nhóm hydroxy vị trí số ,tuy nhiên dẫn xuất vịng thơm cịn chưa nghiên cứu nhiều Vì vậy, thực nghiên cứu đề tài “Tổng hợp số dẫn xuất 7- hydroxy-4-methylcoumarin” với tổng hợp hợp chất trực tiếp vòng thơm nhóm brom, nitro…[5,12] 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 Đề tài gồm có hai nhiệm vụ chính: 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 Tổng hợp số dẫn xuất 7-hydroxy-4-methylcoumarin 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 3-bromo-7-hydroxy-4-methylcoumarin (B) 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 3,6,8-tribromo-7-hydroxy-4-methylcoumarin (C) fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 7-hydroxy-4-methyl-6-nitrocoumarin (D) 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7-hydroxy-4-methyl-8-nitrocoumarin (E) 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 7-methoxy-4-methyl-6-nitrocoumarin (F) df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 Nghiên cứu cấu trúc chất tổng hợp phương pháp vật lý 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e đại phổ hồng ngoại, phổ cộng hưởng từ hạt nhân 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công PHẦN 1: TỔNG QUAN 1.KHÁI QUÁT VỀ COUMARIN Coumarin dẫn chất α–pyron có cấu trúc C -C Benzo α–pyron chất coumarin đơn giản tồn thực vật biết từ năm 1820 hạt Dipteryx odorata Willd, thuộc họ Đậu (hình 1) Cây mọc Brazil, có trồng Venezuela cịn có tên địa phương “Coumarou”, mà benzo α-pyron cịn có tên coumarin Benzo α–pyron cịn có Asperula odorata L họ Cà phê, số thuộc chi Melilotus họ Đậu Chất có mùi thơm dễ O O α-pyron O O Benzo α-pyron chịu, dùng làm hương liệu Coumarin chất kết tinh không màu, số lớn dễ thăng hoa có mùi thơm Ở dạng kết hợp glycosid tan nước, dạng aglycon dễ tan dung mơi phân cực Các dẫn xuất coumarin có huỳnh quang ánh sáng tử ngoại Ngoài hợp chất phổ biến loại thuốc chữa bệnh như: Cỏ mực, Ba dót, Mần tưới, Bạch chỉ, Tiền Hồ, Sà sàng, Ammi visnaga, Sài đất, Mù u, 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 Hoàng kỳ, Cúc La Mã, Quế… 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b Chúng ta thu dẫn xuất coumarin phương pháp chiết suất f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b trực tiếp hay tổng hợp gián tiếp [14] 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e Hình 1: CâyDipteryx odorata Willd 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công PHÂN LOẠI COUMARIN Cho đến người ta biết 200 chất coumarin khác phương pháp chiết suất từ hợp chất thiên nhiên phương pháp tổng hợp Chúng ta phân loại coumarin thành nhóm với đại diện tiêu biểu sau theo tài liệu tham khảo [14] R5 2.1 Coumarin đơn giản R4 R R3 R6 R7 O O Chú thích: Glc: glucopyranoside R8 R 2.1.1 Nhóm oxycoumarin Tên chất Coumarin Điểm chảy (oC) Nhóm 70 Umbelliferon 223-224 R = OH Skimmin 219-221 Umbelliferon -7-O-glc Neohydrangin 204 Umbelliferon -7-O-glc-glc 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e Aesculetin 268-272 e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 R = R = OH 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b Aesculin (aesculosid) 205 Aesculetin -6-O-glc f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b Cichoriin 213-216 Aesculetin -6-O-glc dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 2.1.2 Nhóm alkyl-oxycoumarin (gốc alkyl thường gốc terpenoid) fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b Tên chất Điểm chảy ( C) 3-methyl-4-oxycoumarin 225 Nhóm o fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b R = CH ; R = OH f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 Osthenol 124-125 R7 = OH; R8 = CH - 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b CH=C(CH ) 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 Vellein 187-189 Osthenol-8-O-glc 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 Osthol 7-demetylsuberosin SVTH: Nguyễn Thị Hồng Thái 83-84 133-134 R7 = OCH ;R = CH - 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a CH=C(CH ) R7 = OH; 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 R6 = CH Trang Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công CH=C(CH ) Suberosin R7 87-88 = OCH ; R = CH - CH=C(CH ) R = OH; Ostruthin 117-119 R = CH -CH=C(CH )-(CH ) CH=(CH ) R = R = OCH ; Aculeatin 113 R6 = CH2 CH C(CH3)2 O R = OCH ; Meransin (oxydosthol) 98 R8 = CH2 CH C(CH3)2 O 2.2 Furanocoumarin (hay furocoumarin) 2.2.1 Nhóm 6,7 furanocoumarin (hay cịn gọi nhóm psoralen) R5 R4 R4' R3 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e R5 ' O O O e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 R8 Tên chất 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b Điểm chảy (oC) f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 Nhóm 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b Psoralen 161-163 R3 R8 = H Bergaptol 276-282 R = OH 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 Bergapten 188-191 R = OCH Xanthotoxol 252-253 R = OH 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 Xanthotoxin 146-147 R = OCH Imperatorin 102-105 R = OCH -CH=C(CH ) df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e Isoimperatorin 112-114 R = OCH -CH=C(CH ) 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d Prangenin 113-114 R8 = OCH2 CH C(CH3)2 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 O 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Oxypeucedanin (racemic) SVTH: Nguyễn Thị Hồng Thái 141-143 R5 = OCH2 CH C(CH3)2 O Trang Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Cơng 2.2.2 Nhóm dihydro 6:7 furanocoumarin R 5' Tên chất O O O O Điểm chảy (oC) Nodakenetin R5' = 195-197 Nodakenin 189 Marmesinin C(CH3)2 (vị trí β) OH 215-219 Marmesin Nhóm R5' = C(CH3)2 O-glc Đồng phân đối quang Nodakenetin Marmesin-β-glucosid 2.2.3 Nhóm 7:8 furanocoumarin (hay cịn gọi nhóm angelicin) R5 R4 R6 R3 O O O 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 R2 ' Tên chất 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a R3' 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 Điểm chảy ( C) 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b Nhóm o dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc Angelicin 138-140 Các nhóm = H Isobergapten 218-222 R = OCH c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b Sphondin 192-193 R = OCH Pimpenellin 117-119 R = R = OCH fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 Oroselon 187-189 R2' = C CH2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b CH3 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 Oroselol SVTH: Nguyễn Thị Hồng Thái 154-156 R2' = CH3 C OH CH3 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Trang Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công Phổ 1H-NMR hợp chất 7-hydroxy-4-methylcoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e O e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b O 4a CH3 CH 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 C H H C fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 HC fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 HO 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 46 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Cơng Phổ IR hợp chất 3-bromo-7-hydroxy-4-methylcoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b O f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 O CH3 c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e HO 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 47 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Cơng Phổ 1H-NMR hợp chất 3-bromo-7-hydroxy-4-methylcoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b O Br 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 O CH3 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e HO 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 48 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công O O CH3 Br Phổ 1H-NMR giãn rộng hợp chất 3-bromo-7-hydroxy-4-methylcoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc HO c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 49 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công O Br Phổ IR hợp chất 3,6,8-tribromo-7-hydroxy-4methylcoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a CH3 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 O 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 Br 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 HO Br df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 50 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Cơng O Br Phổ 1H-NMR hợp chất 3,6,8-tribromo-7-hydroxy-4-methylcoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a CH3 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b O f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 Br fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b HO Br f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 51 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công Phổ IR hợp chất 7-hydroxy-4-methyl-8-nitrocoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a O 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 O CH3 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e HO 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 52 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công Phổ 1H-NMR hợp chất 7-hydroxy-4-methyl-8-nitrocoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 O 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 O CH3 e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 NO2 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b HO 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 53 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công HO NO2 O CH3 O Phổ giãn rộng 1H-NMR hợp chất 7-hydroxy-4-methyl-8-nitrocoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 54 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công O Phổ IR hợp chất 7-hydroxy-4-methyl-6-nitrocoumarin CH3 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 O 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 HO O2N 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 55 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công Phổ 1H-NMR hợp chất 7-hydroxy-4-methyl-6-nitrocoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b O f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b CH3 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca O e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e HO O2N 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 56 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công O CH3 O Phổ giãn rộng 1H-NMR hợp chất 7-hydroxy-4-methyl-6-nitrocoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b HO O2N 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 57 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Cơng Phỗ IR hợp chất 7-methoxy-4-methyl-6-nitrocoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b O dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 CH3 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 O 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 SVTH: Nguyễn Thị Hồng Thái H3CO O2N 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Trang 58 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công Phổ 1H-NMR hợp chất 7-methoxy-4-methyl-6-nitrocoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 O 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 CH3 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b O 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 H3CO O2N 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 59 Khóa luận tốt nghiệp GVHD: TS Nguyễn Tiến Công Phổ giãn rộng 1H-NMR hợp chất 7-methoxy-4-methyl-6-nitrocoumarin 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b O f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b CH3 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca O e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e H3CO O2N 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 SVTH: Nguyễn Thị Hồng Thái Trang 60