Hóa hữu cơ bai giang

Hóa Hữu Cơ Organic Chemistry TS Phạm Ngọc Tuấn Anh Terpen (1R,5R)-(+)-α-pinen (1S,5S)-(−)-α-pinen Isopren Limonen farnesol 2-methyl-1,3-butadien Terpen terpenoid retinol Terpen Hydrocarbon chưa no có cơng thức chung (C5H8)n, tạo thành đơn vị mạch vòng, theo nguyên tắc cộng hợp “đầu-đi” Monoterpen Isopren Đầ u isopren liên kết với dạng mạch hở hay + Đuô i Đầ u Đuô i Terpen Monoterpen Isopren Đầ u + Đuô i Đầ u isopren Đuô i monoterpen monoterpen voø ng n=1 Hemiterpen n=2 Monoterpen (C5H8)2 n=3 Sesquiterpen (C5H8)3 n=4 Diterpen (C5H8)4 n=6 Triterpen (C5H8)6 n=8 Tetraterpen (C5H8)8 n=n Polyterpen (C5H8)n sesquiterpen C 5H triterpen voø ng Monoterpen Myrcen β-Myrcen Myrcia rostrata 7-Methyl-3-methylen-1,6-octadien O O3 O C α-Myrcen Aceton  2-Methyl-6-methylen -1,7-octadien Myrcen + CHO CHO Cetodialdehyd + 2HCHO Aldehyd formic Monoterpen α-Ocimen β-Ocimen 3,7-dimethyl-1,3,7-octatrien 3,7-dimethyl-1,3,6-octatrien CHO O3 O C CHO CH3 + 2HCHO + C O Aldehyd pyruvic Ocimen CH3COOH + HOOC-CH2-COOH acid malonic Monoterpen CH2OH H3C CH2OH CH3 CH3 cis Nerol trans Geraniol 3,7-dimetyl-2,6-octadienol-1 H2C CH3 trans Geraniol H3C CH2OH H2C CH2OH CH3 cis Nerol 3,7-dimetyl-2,7-octadienol-1 Dạng β Dạng α CHO CHO CHO H3C CH3 H3C Geranial Neral Citral A Citral B 3,7-dimethyl-2,6-octadienal CH3 H3C CH3 Monoterpen Tổng hợp Citral B C2H5OOC BrCH2 C2H5OOC C2H2 HC C OH + H H2C CH OH + PBr3 C C C C NaNH2 H C - HBr CH3 H3C CH3 CH3 CH3 CH3 O CH3 O O CH3 CH3 OH H2O , HO - C2H5OH , -CO2 CH3 O +ClCH2COOC2H5 CH3 CH3 COOC2H5 CH3 COOC2H5 - H2O CH3 CH3 +H2O CHO - C2H5OH - H2O CH3 CH3 Citral B Monoterpen (+)-Citronellol (−)-citronellol (+)-Citronellol 3,7-dimethyloct-6-en-1-al 3,7-Dimethyloct-6-en-1-ol Cymbopogon citratus Triterpen 22 23 24 15 18 22 23 Squalen 18 19 14 19 24 10 15 14 10 Tetraterpen Khung β-ionon CH3 H H H H CH3 H H H H H CH3 H H H H CH3 H Khung α-ionon αα-Caroten − Caroten Khung β-ionon CH3 H H H H CH3 H H H H H β-Caroten β− Caroten Khung β-ionon CH3 H H H H CH3 H H H γ − Caroten ϒ-Caroten H H H CH3 H H H CH3 H Mộ t nử a phâ n tửLicopen H CH3 H H H CH3 H Khung β-ionon Tetraterpen Astaxanthin Tetraterpen CH3 H H H H CH3 H H H H H Licopen Licopen H CH3 H H H CH3 H Tetraterpen Licopen γ −Caroten β−Caroten α−Caroten CH2OH Vitam in A Vitamin A1 Retinol Steroid Steroid Gonan 2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17-Hexadecahydro-1Hcyclopenta[a]phenanthren Tetracyclo[8.7.0.0 2,7 11,15 ]heptadecan 5α-Gonan 5β-Gonan Steroid Steran (Gonan) Pregnan Estran Androstan Cholan Cholestan Steroid Cholestan R CH3 CH3 10 H9 H H 13 R H CH3 17 CH3 14 H 10 5α 13 H H H 14 H 5β Cholestan Coprostan A/B trans A/B cis B/C trans B/C trans C/D trans C/D trans Dãy 5α (dãy normal) Dãy 5β (dãy allo) 17 H Steroid CH3 CH3 3α HO 10 H H 13 CH3 H 17 14 H H 3α − Cholest anol CH3 3β HO 10 H H 14 H H 3β− Cholest anol H Steroid o Sterol Cholesterol (3β)-Cholest-5-en-3-ol Ergosterol (3β)- Ergosta-5,7,22-trien-3-ol Steroid o Acid mật Acid cholic 3α,7α,12α-Trihydroxy-5β-cholanoic acid Steroid o Hormon 21 19 Khung Estran Estrogen 18 18 18 Khung Androstan Androgen 20 19 Khung Pregnan Progestagen Mineralocorticoid Glucocorticoid Steroid o Hormon Testosteron 17β-Estradiol Steroid o Hormon Progesteron Dexamethason ... Isopren Limonen farnesol 2-methyl-1,3-butadien Terpen terpenoid retinol Terpen Hydrocarbon chưa no có cơng thức chung (C5H8)n, tạo thành đơn vị mạch vòng, theo nguyên tắc cộng hợp “đầu-đi” Monoterpen