Phản ứng Suzuki-Miyaura - Đại học khoa học tự- 123docz.net

KẾT LUẬN

Trong khóa luâ ̣n này chúng tôi đã tổng hợp được 9 dẫn xuất peptie-biphenyl đối xứng và 19 dẫn xuất peptit -biphenyl không đối xứng dựa trên sáu acid amin cu ̣ thể là prolin, glycin, alanin, phenylalanin, leucin và threonin. Các dẫn xuất thu được mở ra mô ̣t con đường tiềm năng để tổng hợp các chất có hoa ̣t tính sinh ho ̣c và ứng dụng của chúng trong lĩnh vực tìm kiếm thuốc mới

Trong thời gian sắp tới chúng tôi sẽ tiến hành thử hoạt tính sinh học của các dẫn xuất thu đươ ̣c và tổng hợp thêm các dẫn xuất peptit -biphenyl khác để có thể nghiên cứu sâu hơn về các đă ̣c điểm cấu trúc cũng như hoa ̣t tính của loa ̣t chất này .

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Phổ

HNMR của peptit biphenyl 13

Phổ

Phổ 1HNMR của peptit biphenyl

Phổ 1HNMR của peptit biphenyl 17

Phổ 13CNMR của peptit biphenyl 17

Phổ 1HNMR của peptit biphenyl

Phổ 1HNMR của peptit biphenyl 20

Phổ 13CNMR của peptit biphenyl 20

Phổ 1HNMR của peptit biphenyl

Phổ 1HNMR của peptit biphenyl 26

hổ 13CNMR của peptit biphenyl 26

Phổ 1HNMR của peptit biphenyl 27

Phổ 1HNMR của peptit biphenyl 29

Phổ 1HNMR của peptit biphenyl 30

Phổ 1HNMR của peptit biphenyl 31

Phổ 1HNMR của peptit biphenyl 32

Phổ 1HNMR của peptit biphenyl

Phổ 1HNMR của peptit biphenyl 35

Phổ 1HNMR của peptit biphenyl 36

Phổ 13CNMR của peptit biphenyl 36

Phổ 1HNMR của peptit biphenyl

Phổ

1HNMR của peptit biphenyl

Phổ 1HNMR của peptit biphenyl

Phổ 1HNMR của peptit biphenyl 44

Phổ 13CNMR của peptit biphenyl 44

Phổ 1HNMR của peptit biphenyl 45

Phổ

Phổ 1HNMR của peptit biphenyl

Phụ lục phổ nhiễu xa ̣ tia X của hơ ̣p peptide-biphenyl 26

Bảng 1: Dƣ̃ liê ̣u và cấu trúc tinh thể để kiểm tra

Chỉ tiêu thông số 26

Công thức phức của đơn tinh thể C50H56N6O10.5

Khối lượng 909.00 Nhiệt độ (K) 0 Hệ tinh thể orthorhombic Nhóm khơng gian P212121 a, Å 9.9955(5) b, Å 15.8364(7) c, Å 31.1356(14) α, deg 90 β, deg 90 γ, deg 90 V, Å3 4928.5(4) Số phân tử trong một ơ mạng (Z) 4 µ, mm-1 0.087 Tổng số tia phản xạ 43863 Số tia phản xạ độc lập 10447 Số tham số 611 Độ sai lệch R[F2>2σ(F2)] 0.0537 w R(F2) 0.1421

Bảng 2 Tọa độ nguyên tƣ̉ (×104) và thơng sớ hoán đổi đẳng hƣớng tƣơng đƣơng (Å2×103) cho viê ̣c kiểm tra.

Nguyên tƣ̉ x y z U(eq) O001 5780(2) 3538.8(17) 6129.3(8) 28.7(6) O002 1678(3) 5248.0(16) 6220.7(8) 29.3(6) O003 1527(2) 3380.6(17) 7103.7(8) 29.3(6) O004 1822(3) 2051.5(16) 6180.1(9) 33.1(6) O005 7541(3) 2491.4(19) 6960.0(9) 36.4(6) O006 3270(3) 6799.4(18) 5663.2(9) 35.2(6) O007 5909(3) 1859.6(17) 6580.6(9) 37.3(7) O008 3609(3) 7816.0(18) 4647.8(9) 36.2(6) O009 131(3) 9402.1(19) 5307.2(11) 45.5(8) N00A 2175(3) 3459.2(19) 6127.2(9) 20.8(6) O00B 1551(3) 10427.3(18) 5111.9(10) 44.7(7) N00C 1356(3) 6687.3(19) 5282.1(9) 25.0(6) N00D 4314(3) 3225(2) 6657.0(9) 25.4(6) N00E 1881(3) 6595.1(19) 6429.0(9) 29.4(7)

N00F -113(3) 3731.0(18) 6636.8(9) 22.7(6) N00G 1564(3) 8248.0(19) 4852.0(11) 33.4(7) C00H 2482(3) 7659(2) 4781.2(11) 25.2(7) C00I 1055(4) 9652(2) 5091.8(13) 32.4(8) C00J 6400(4) 2467(2) 6832.9(11) 26.8(8) C00K 1444(3) 2782(2) 6232.7(11) 22.8(7) C00L 2129(3) 5774(2) 6474.3(11) 23.1(7) C00M 4638(3) 3413(2) 6245.6(11) 21.9(7) C00N 2548(4) 3822(2) 5215.9(10) 24.3(7) C00O 3474(3) 3368(2) 5924.4(10) 22.1(7) C00P 616(3) 3867(2) 6994.1(11) 24.3(7) C00Q 2565(3) 5255(2) 7235.3(11) 22.4(7) C00R 3033(3) 5528(2) 6837.9(11) 22.4(7) C00S -1106(3) 4300(2) 6440.8(12) 26.9(7) C00T 1499(4) 4390(2) 5165.3(12) 28.5(8) C00U 5325(4) 5373(2) 7074.5(13) 31.8(8) C00V 216(3) 4611(2) 7260.1(11) 26.6(8) C00W -1098(4) 4008(3) 5973.0(11) 30.0(8) C00X 3632(3) 3976(2) 5547.5(11) 25.0(7) C00Y 2558(4) 3086(2) 4970.3(11) 29.1(8) C00Z 4861(4) 5099(3) 7466.8(13) 32.3(9) C010 491(4) 3487(3) 4635.8(12) 32.8(9) C011 1648(4) 6530(3) 4068.0(12) 31.8(8) C012 2053(4) 6776(2) 5649.8(11) 26.2(7) C013 472(4) 4222(2) 4879.7(12) 30.9(8) C014 1114(3) 5260(2) 7361.4(11) 25.2(7) C015 1059(4) 6451(2) 4516.1(12) 29.6(8) C016 5353(3) 3100(2) 6971.8(11) 26.1(8) C017 2025(4) 6753(2) 4868.4(11) 26.3(7) C018 1531(4) 2918(3) 4680.9(12) 31.8(8) C019 4408(4) 5583(2) 6757.6(12) 28.0(8) C01A -1067(4) 4628(3) 7430.5(13) 39.4(10) C01B 40(3) 2943(2) 6395.2(11) 24.8(7) C01C 3507(4) 5043(3) 7547.0(11) 29.1(8) C01D 1240(5) 7180(3) 3798.5(13) 37.9(9) C01E -942(4) 3064(3) 6013.9(12) 30.3(8) C01F 1241(4) 9350(2) 4307.7(14) 35.5(9) C01G -1477(4) 5274(4) 7696.5(15) 51.6(13) C01H 1181(4) 6909(2) 6047.4(12) 31.9(9)

C01I 668(4) 5932(3) 7614.2(13) 39(1) C01J 2603(4) 5956(3) 3922.9(13) 35.3(9) C01K 1767(4) 9137(2) 4753.9(14) 32.7(9) C01L 3135(5) 6031(3) 3513.7(14) 43.6(10) C01M 1795(5) 7263(3) 3392.3(13) 44.1(11) C01N -626(4) 5932(4) 7781.0(16) 55.8(14) C01O 2737(5) 6688(3) 3249.9(13) 46.2(11) C01P 2330(5) 7288(3) 6711.6(13) 38.2(10) C01Q 4730(4) 2804(3) 7393.1(12) 40.2(10) C01R 6831(5) 1212(3) 6443.6(15) 46.1(11) C01S 1031(6) 7860(3) 6140.2(14) 51.3(13) C01T 912(7) 10985(3) 5426.4(15) 60.5(15) O01U 3557(6) 821(4) 6511(3) 129(2) C01V 1347(9) 7971(4) 6613(2) 97(3)

Bảng 3: Thông sớ thay thế khơng đẳng hƣớng (Å2×103) cho kiểm tra . Các yếu tố thay thế không đẳng hƣớng chuyển số mũ có dạng : - 2π2[h2a*2U11+2hka*b*U12+…].

Atom U11 U22 U33 U23 U13 U12

O001 18.2(12) 40.9(15) 27.1(13) -1.0(11) 1.3(10) 4.5(10) O002 34.3(14) 28.6(13) 24.9(12) 0.4(11) -6.8(11) -2.3(11) O003 23.7(12) 38.9(14) 25.5(12) 1.8(11) -5(1) 0.3(11) O004 31.8(14) 24.8(13) 42.6(15) -5.9(12) 1.7(12) 0.8(11) O005 23.5(13) 50.7(17) 35.1(14) 0.9(13) -4.1(12) 12.5(12) O006 25.7(14) 46.8(16) 33.1(14) -3.3(13) -10.6(11) 8.0(12) O007 37.7(15) 34.7(15) 39.4(15) -3.5(13) -5.8(12) 9.1(12) O008 24.5(13) 43.8(16) 40.3(15) -3.4(13) 2.7(12) -2.8(12) O009 46.1(18) 33.8(15) 56.4(19) -6.5(14) 12.4(16) -4.4(13) N00A 17.0(13) 24.4(14) 20.9(13) -1.5(11) -2.0(11) 2.1(11) O00B 62(2) 32.4(15) 39.4(15) -1.8(13) -10.2(15) -16.7(14) N00C 22.4(14) 27.3(15) 25.4(14) 0.5(12) -5.3(12) 1.8(12) N00D 16.2(13) 39.0(17) 21.0(14) 1.5(13) -2.1(11) 4.6(12) N00E 37.1(17) 30.0(16) 21.0(14) -2.7(13) -7.4(13) 8.5(14) N00F 19.3(14) 27.3(15) 21.5(13) -2.7(12) -1.9(11) 0.0(11) N00G 21.2(15) 24.8(15) 54(2) 2.4(15) 3.4(14) -3.0(12) C00H 21.4(17) 32.6(19) 21.7(16) -3.1(15) -5.3(14) -1.1(14) C00I 33(2) 25.1(18) 40(2) 4.0(17) -12.3(17) -2.9(16) C00J 24.3(18) 32.7(19) 23.3(17) 4.8(15) -1.1(14) 8.6(15)

C00K 23.4(17) 23.1(17) 21.9(15) -4.2(14) -4.1(13) -0.2(13) C00L 21.9(16) 27.5(18) 19.8(15) -0.2(14) 1.0(13) 0.0(13) C00M 17.1(16) 25.1(17) 23.4(16) -2.2(14) 0.3(13) 5.8(13) C00N 25.3(17) 30.7(18) 17.0(15) 1.7(14) 1.5(13) -5.0(14) C00O 18.2(15) 27.2(17) 20.8(15) -1.8(14) -0.8(13) 5.1(13) C00P 19.1(16) 34.1(19) 19.7(16) 2.8(15) 0.1(13) -4.2(14) C00Q 17.0(16) 28.7(18) 21.5(15) -3.8(14) -1.6(13) 1.3(13) C00R 23.3(16) 22.9(16) 20.9(16) -3.1(14) -1.4(13) 4.7(13) C00S 18.3(16) 34.0(19) 28.5(18) -2.0(15) -2.2(14) 4.1(14) C00T 32.6(19) 26.1(18) 26.8(17) 2.9(15) -4.1(15) -5.1(15) C00U 17.4(17) 38(2) 40(2) 3.6(18) 3.3(15) 1.2(15) C00V 18.3(16) 42(2) 19.0(16) -5.5(16) -2.1(13) -4.1(15) C00W 20.9(17) 45(2) 24.4(17) 0.9(17) -7.4(14) 2.7(16) C00X 22.5(17) 32.2(18) 20.3(16) 0.9(15) -1.2(13) -1.2(14) C00Y 30.7(19) 34(2) 22.9(17) -0.8(15) 3.0(15) 1.0(16) C00Z 20.0(18) 44(2) 33(2) 8.6(18) -6.8(15) 2.4(15) C010 33(2) 41(2) 23.9(18) 2.4(17) -4.0(15) -11.6(17) C011 38(2) 32.8(19) 24.3(17) -3.6(16) -9.5(16) -6.2(17) C012 29.0(18) 24.3(17) 25.2(17) 0.9(15) -6.3(14) 6.7(14) C013 30.0(19) 33(2) 29.8(19) 6.7(16) -6.7(15) -2.8(16) C014 16.5(16) 41(2) 17.9(15) -4.2(15) -2.0(13) 0.0(15) C015 32(2) 27.2(17) 29.1(18) -0.5(15) -7.1(16) -4.5(16) C016 18.6(16) 38(2) 21.9(16) 1.8(15) -3.5(13) 6.3(15) C017 27.9(18) 28.6(18) 22.2(16) -2.2(15) -4.8(14) 5.0(15) C018 35(2) 39(2) 22.4(17) -5.7(16) 3.3(15) -10.3(17) C019 24.3(18) 32.4(19) 27.4(18) 2.6(16) 6.6(14) -2.8(15) C01A 21.7(18) 65(3) 32(2) -17(2) 2.2(16) -10.9(19) C01B 20.6(17) 27.0(18) 26.8(17) -3.0(15) -4.6(14) -3.3(13) C01C 24.4(18) 43(2) 20.0(16) 4.9(16) -1.4(14) -0.9(15) C01D 53(3) 33(2) 27.7(19) -4.4(17) -10.6(18) -1.3(19) C01E 19.8(17) 43(2) 27.9(18) -10.2(17) -5.8(15) -2.3(15) C01F 30(2) 29.8(19) 47(2) 0.6(18) 6.6(18) -3.9(16) C01G 17.9(18) 93(4) 44(2) -35(3) 6.1(18) -5(2) C01H 36(2) 36(2) 23.5(17) 0.2(16) -2.4(16) 13.8(17) C01I 21.0(18) 59(3) 37(2) -24(2) -3.4(16) -4.6(18) C01J 41(2) 32(2) 33(2) -4.7(17) -9.1(18) -4.0(17) C01K 22.9(18) 25.3(18) 50(2) 3.4(17) -1.4(17) -6.3(15) C01L 38(2) 56(3) 37(2) -15(2) -4.8(18) -4(2) C01M 62(3) 44(2) 26.7(19) 1.0(18) -11.1(19) -9(2)

C01N 23(2) 92(4) 52(3) -47(3) 0.8(19) 2(2) C01O 51(3) 63(3) 24.2(18) -4(2) -8.3(19) -18(2) C01P 49(3) 31(2) 34(2) -9.0(17) -13.9(19) 9.0(18) C01Q 30(2) 65(3) 25.6(19) 8(2) 0.7(16) 16(2) C01R 67(3) 34(2) 38(2) -0.2(19) -4(2) 20(2) C01S 74(3) 42(2) 38(2) 1(2) -4(2) 34(2) C01T 112(5) 33(2) 37(2) -10(2) -9(3) -15(3) O01U 89(4) 110(4) 189(7) -17(5) -16(5) 5(3) C01V 145(7) 49(3) 97(5) -26(3) -69(5) 40(4)

Bảng 4: Chiều dài liên kết cho kiểm tra.

Nguyên tƣ̉ Nguyên tƣ̉ Độ dài/Å Nguyên tƣ̉ Nguyên tƣ̉ Độ dài/Å

O001 C00M 1.215(4) C00P C00V 1.495(5) O002 C00L 1.233(4) C00Q C00R 1.392(5) O003 C00P 1.240(4) C00Q C014 1.502(5) O004 C00K 1.228(4) C00Q C01C 1.393(5) O005 C00J 1.208(4) C00R C019 1.400(5) O006 C012 1.217(5) C00S C00W 1.528(5) O007 C00J 1.336(5) C00T C013 1.384(5) O007 C01R 1.443(5) C00U C00Z 1.377(6) O008 C00H 1.226(4) C00U C019 1.387(5) O009 C00I 1.208(5) C00V C014 1.400(5) N00A C00K 1.338(4) C00V C01A 1.388(5)

N00A C00O 1.451(4) C00W C01E 1.509(6)

O00B C00I 1.325(5) C00Y C018 1.392(5)

O00B C01T 1.465(6) C00Z C01C 1.379(5) N00C C012 1.348(4) C010 C013 1.389(6) N00C C017 1.455(5) C010 C018 1.384(6) N00D C00M 1.354(4) C011 C015 1.519(5) N00D C016 1.441(4) C011 C01D 1.389(6) N00E C00L 1.331(5) C011 C01J 1.394(6) N00E C01H 1.465(5) C012 C01H 1.528(5)

N00E C01P 1.477(5) C014 C01I 1.397(6) N00F C00P 1.347(4) C015 C017 1.538(5) N00F C00S 1.473(4) C016 C01Q 1.526(5) N00F C01B 1.465(5) C01A C01G 1.379(6) N00G C00H 1.326(5) C01B C01E 1.552(5) N00G C01K 1.454(5) C01D C01M 1.387(6) C00H C017 1.531(5) C01F C01K 1.523(6) C00I C01K 1.511(6) C01G C01N 1.370(7) C00J C016 1.512(5) C01H C01S 1.541(6) C00K C01B 1.514(5) C01I C01N 1.393(6) C00L C00R 1.500(5) C01J C01L 1.386(6) C00M C00O 1.535(4) C01L C01O 1.383(7) C00N C00T 1.389(5) C01M C01O 1.383(7) C00N C00X 1.517(5) C01P C01V 1.493(7) C00N C00Y 1.395(5) C01S C01V 1.515(8) C00O C00X 1.526(5)

Bảng 5 Góc liên kết cho kiểm tra. Nguyên

tƣ̉ Nguyên tƣ̉ Nguyên tƣ̉ Góc/˚ Nguyên tƣ̉ Nguyên tƣ̉ Nguyên tƣ̉ Góc/˚

C00J O007 C01R 116.8(3) C01A C00V C00P 118.3(3) C00K N00A C00O 121.1(3) C01A C00V C014 119.5(3) C00I O00B C01T 115.2(4) C01E C00W C00S 102.7(3) C012 N00C C017 120.4(3) C00N C00X C00O 110.4(3) C00M N00D C016 120.1(3) C018 C00Y C00N 120.6(4) C00L N00E C01H 120.4(3) C00U C00Z C01C 120.8(4) C00L N00E C01P 127.3(3) C018 C010 C013 120.1(3) C01H N00E C01P 112.1(3) C01D C011 C015 120.1(4) C00P N00F C00S 127.5(3) C01D C011 C01J 119.2(4) C00P N00F C01B 120.2(3) C01J C011 C015 120.6(4) C01B N00F C00S 112.2(3) O006 C012 N00C 123.3(3)