(E)-11-十四碳烯-1-醇合成路线 （共 56 条）
反应条件
1: 51 percent / dimethylsulfoxide / 16 h / Ambient temperature 2: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.) 20 deg C, 12 h 3: p-TsOH / methanol / 2 h / Heating 4: 90 percent / LiAlH4 / 1,2-dimethoxy-ethane / 48 h / 140 °C View Scheme
参考文献
Canevet; Roeder; Vostrowsky; Bestmann
Chemische Berichte, 1980 , vol. 113, # 3 p. 1115 - 1120
反应条件
1: 90 percent / bromine / CCl4 / 0.5 h / 20 °C 2: 75 percent / 18-crown-6-ether, KOH / petroleum ether / 10 h / 90 - 110 °C 3: 1) n-BuLi / 1) benzene + THF, 20 deg C, 1 h; 2) HMPTA, 20 deg C, 6 h. 4: 97 percent / LiAlH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 10 h / 140 °C View Scheme
参考文献
Zakharkin, L. I.; Guseva, V. V.
Chemistry of Natural Compounds, 1984 , vol. 20, # 6 p. 733 - 736
Khimiya Prirodnykh Soedinenii, 1984 , vol. 20, # 6 p. 776 - 779
反应条件
1: 71 percent / stearic acid, palmitic acid / 350 °C / 260 Torr 2: 90 percent / bromine / CCl4 / 0.5 h / 20 °C 3: 75 percent / 18-crown-6-ether, KOH / petroleum ether / 10 h / 90 - 110 °C 4: 1) n-BuLi / 1) benzene + THF, 20 deg C, 1 h; 2) HMPTA, 20 deg C, 6 h. 5: 97 percent / LiAlH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 10 h / 140 °C View Scheme
参考文献
Zakharkin, L. I.; Guseva, V. V.
Chemistry of Natural Compounds, 1984 , vol. 20, # 6 p. 733 - 736
Khimiya Prirodnykh Soedinenii, 1984 , vol. 20, # 6 p. 776 - 779
反应条件
1: 65 percent / ethyl acetate / 450 - 470 °C / quartz tube packed with glass 2: 98 percent / KOH / methanol; H2O / 8 h / Heating 3: 90 percent / bromine / CCl4 / 0.5 h / 20 °C 4: 75 percent / 18-crown-6-ether, KOH / petroleum ether / 10 h / 90 - 110 °C 5: 1) n-BuLi / 1) benzene + THF, 20 deg C, 1 h; 2) HMPTA, 20 deg C, 6 h. 6: 97 percent / LiAlH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 10 h / 140 °C View Scheme
参考文献
Zakharkin, L. I.; Guseva, V. V.
Chemistry of Natural Compounds, 1984 , vol. 20, # 6 p. 733 - 736
Khimiya Prirodnykh Soedinenii, 1984 , vol. 20, # 6 p. 776 - 779
反应条件
1: 98 percent / KOH / methanol; H2O / 8 h / Heating 2: 90 percent / bromine / CCl4 / 0.5 h / 20 °C 3: 75 percent / 18-crown-6-ether, KOH / petroleum ether / 10 h / 90 - 110 °C 4: 1) n-BuLi / 1) benzene + THF, 20 deg C, 1 h; 2) HMPTA, 20 deg C, 6 h. 5: 97 percent / LiAlH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 10 h / 140 °C View Scheme
参考文献
Zakharkin, L. I.; Guseva, V. V.
Chemistry of Natural Compounds, 1984 , vol. 20, # 6 p. 733 - 736
Khimiya Prirodnykh Soedinenii, 1984 , vol. 20, # 6 p. 776 - 779
反应条件
1: PBr3 / 1.) pyridine, hexane, 3-5 deg C, 3h; 2.) 20 deg C, 12 h 2: 79 percent / Li2CuCl4 / 1.) THF, 0 deg C, 5 h; 2.) 20 deg C, 1 h View Scheme
参考文献
Zakharkin, L. I.; Petrushkina, E. A.
Journal of Organic Chemistry USSR (English Translation), 1982 , vol. 18, # 8 p. 1419 - 1422
Zhurnal Organicheskoi Khimii, 1982 , vol. 18, # 8 p. 1623 - 1628
反应条件
1: 1.) 0.75M 9-borabicyclo<3.3.1>nonane; 2.) 3N NaOH, 26percent H2O2 / 1.) THF, 0 deg C, 2-3 h; 2.) 20 deg C, 2-3 h 2: PBr3 / 1.) pyridine, hexane, 3-5 deg C, 3h; 2.) 20 deg C, 12 h 3: 79 percent / Li2CuCl4 / 1.) THF, 0 deg C, 5 h; 2.) 20 deg C, 1 h View Scheme
参考文献
Zakharkin, L. I.; Petrushkina, E. A.
Journal of Organic Chemistry USSR (English Translation), 1982 , vol. 18, # 8 p. 1419 - 1422
Zhurnal Organicheskoi Khimii, 1982 , vol. 18, # 8 p. 1623 - 1628
反应条件
1: 1.) Mg / 1.) THF, 2.) THF, -15 deg C, 1 h, 20 deg C, 12 h 2: 93 percent / DMAP / pyridine / 48 h 3: 85 percent / CuI / tetrahydrofuran / 2 h / -10 °C 4: 1.) BBN, 2.) H2O2, NaOAc / 1.) THF, 10 deg C, 2 h, 2.) THF, H2O, 25 deg C, 2 h View Scheme
参考文献
Ishmuratov; Yakovleva; Kharisov; Muslukhov; Tolstikov
Russian Chemical Bulletin, 1997 , vol. 46, # 5 p. 1035 - 1037
反应条件
1: 93 percent / DMAP / pyridine / 48 h 2: 85 percent / CuI / tetrahydrofuran / 2 h / -10 °C 3: 1.) BBN, 2.) H2O2, NaOAc / 1.) THF, 10 deg C, 2 h, 2.) THF, H2O, 25 deg C, 2 h View Scheme
参考文献
Ishmuratov; Yakovleva; Kharisov; Muslukhov; Tolstikov
Russian Chemical Bulletin, 1997 , vol. 46, # 5 p. 1035 - 1037
反应条件
1: 85 percent / CuI / tetrahydrofuran / 2 h / -10 °C 2: 1.) BBN, 2.) H2O2, NaOAc / 1.) THF, 10 deg C, 2 h, 2.) THF, H2O, 25 deg C, 2 h View Scheme
参考文献
Ishmuratov; Yakovleva; Kharisov; Muslukhov; Tolstikov
Russian Chemical Bulletin, 1997 , vol. 46, # 5 p. 1035 - 1037
