顺-11-十四碳烯-1-醇合成路线 （共 34 条）
反应条件
1: p-TsOH / diethyl ether
2: 51 percent / dimethylsulfoxide / 16 h / Ambient temperature
3: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.) 20 deg C, 12 h
4: p-TsOH / methanol / 2 h / Heating
5: 95 percent / H2, quinoline / Lindlar catalyst / pentane / 1 h / -10 °C
View Scheme
参考文献
Rossi, Renzo; Carpita, Adriano; Gaudenzi, Loretta; Quirici, Maria Grazia
Gazzetta Chimica Italiana, 1980 , vol. 110, # 4 p. 237 - 246
反应条件
1: p-TsOH / methanol / 2 h / Heating
2: 95 percent / H2, quinoline / Lindlar catalyst / pentane / 1 h / -10 °C
View Scheme
参考文献
Rossi, Renzo; Carpita, Adriano; Gaudenzi, Loretta; Quirici, Maria Grazia
Gazzetta Chimica Italiana, 1980 , vol. 110, # 4 p. 237 - 246
反应条件
1: 1) n-BuLi / 1) benzene + THF, 20 deg C, 1 h; 2) HMPTA, 20 deg C, 6 h.
2: 95 percent / hydrogen, quinoline / 5percent Pd/BaSO4 / hexane / 20 °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: 75 percent / 18-crown-6-ether, KOH / petroleum ether / 10 h / 90 - 110 °C
2: 1) n-BuLi / 1) benzene + THF, 20 deg C, 1 h; 2) HMPTA, 20 deg C, 6 h.
3: 95 percent / hydrogen, quinoline / 5percent Pd/BaSO4 / hexane / 20 °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
C32H41N3O4Ru in tetrahydrofuran
Inert atmosphere; chemoselective reaction;
参考文献
Herbert, Myles B.; Marx, Vanessa M.; Pederson, Richard L.; Grubbs, Robert H.
Angewandte Chemie - International Edition, 2013 , vol. 52, # 1 p. 310 - 314
Angew. Chem., 2012 , vol. 125, # 1 p. 328 - 332,5
反应条件
lithium aluminium tetrahydride in tetrahydrofuran
4 h; Heating;
参考文献
Vinczer, Peter; Juvancz, Zoltan; Novak, Lajos; Szantay, Csaba
Acta Chimica Hungarica, 1988 , vol. 125, # 6 p. 797 - 820
反应条件
1: 85 percent / PBr3 / benzene / 5 h / Ambient temperature
2: 22 g / acetonitrile / 8 h / Heating
3: 1.) potassium tert-butanolate / 1.) DMF, 20 deg C, 3h, 2.) 5h
4: LiAlH4 / diethyl ether / 3 h / Heating
View Scheme
参考文献
Dzhemilev, U. M.; Balezina, G. G.; Volkova, L. A.; Krivonogov, V. P.; Tolstikov, G. A.
Chemistry of Natural Compounds, 1980 , vol. 16, # 1 p. 82 - 85
Khimiya Prirodnykh Soedinenii, 1980 , vol. 16, # 1 p. 97 - 102
反应条件
1: 72 percent / dipotassium diazenedicarboxylate / pyridine; methanol; acetic acid / 25 h
2: 1.) tetrakis<triphenylphosphine>-palladium / 1.) benzene, room temp., 15 min, 2.) room temp., overnight
3: p-toluenesulfonic acid monohydrate / methanol; H2O / 2 h / 50 °C
View Scheme
参考文献
Michelot, Didier
Synthesis, 1983 , # 2 p. 130 - 134
反应条件
1: 1.) tetrakis<triphenylphosphine>-palladium / 1.) benzene, room temp., 15 min, 2.) room temp., overnight
2: p-toluenesulfonic acid monohydrate / methanol; H2O / 2 h / 50 °C
View Scheme
参考文献
Michelot, Didier
Synthesis, 1983 , # 2 p. 130 - 134
反应条件
9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran
参考文献
Bestmann; Kantardjiew; Roesel; et al.
Chemische Berichte, 1978 , vol. 111, # 1 p. 248 - 253
