(Z,E)-十三-4,7-二烯-1-醇合成路线 （共 44 条）
反应条件
1.1: EtMgBr / tetrahydrofuran / 2 h / 20 °C
1.2: cuprous cyanide / hexamethylphosphoric acid triamide; tetrahydrofuran / 50 °C
2.1: conc. H2SO4 / CCl4 / Heating
3.1: LiAlH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 20 h / 145 - 150 °C
View Scheme
参考文献
Gansca, Lucia; Gocan, Alexandra; Oprean, Ioan; Maxim, Sanda; Budae, Iuliana
Revue Roumaine de Chimie, 2001 , vol. 46, # 11 p. 1243 - 1248
反应条件
1: 1.) Mg / 1.) Et2O, 2.) Et2O, -15 deg C, 0.5 h, -15 to 0 deg C, 0.5 h
2: 68 percent / propionic acid / 2 h / 136 - 139 °C
3: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature
4: 89 percent / LiAlH4 / diethyl ether / 2 h / 0 °C
View Scheme
参考文献
Odinokov; Vakhidov; Shakhmaev; Zorin
Chemistry of Natural Compounds, 1997 , vol. 33, # 3 p. 350 - 352
反应条件
1: 67 g / NaCl / dimethylsulfoxide; H2O / 40 h / Heating
2: 35.5 g / aq. KOH / methanol / 4 h / Heating
3: 1.) EtMgBr, 2.) CuCN, HMPT / 1.) THF, RT, 2 h, 2.) THF, 3 h
4: 79 percent / conc. H2SO4 / CCl4 / 10 h
5: LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 20 h / 145 - 150 °C
View Scheme
参考文献
Gocan, Alexandra; Gansca, Lucia; Oprean, Ioan
Revue Roumaine de Chimie, 1995 , vol. 40, # 3 p. 253 - 258
反应条件
1: 35.5 g / aq. KOH / methanol / 4 h / Heating
2: 1.) EtMgBr, 2.) CuCN, HMPT / 1.) THF, RT, 2 h, 2.) THF, 3 h
3: 79 percent / conc. H2SO4 / CCl4 / 10 h
4: LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 20 h / 145 - 150 °C
View Scheme
参考文献
Gocan, Alexandra; Gansca, Lucia; Oprean, Ioan
Revue Roumaine de Chimie, 1995 , vol. 40, # 3 p. 253 - 258
反应条件
1: 74 percent / PBr3, pyridine / diethyl ether / 1a) overnight, 2) reflux, 2 h
2: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h
3: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C
4: 54 percent / lithium aluminium monoethoxy hydride / diethyl ether
View Scheme
参考文献
Vig, O. P.; Sharma, M. L.; Kumari, Sarla; Rani, Veena
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985 , vol. 24, p. 675 - 676
反应条件
1: 52 percent / LAH / diethyl ether / 1a) overnight, 1b) reflux, 6 h
2: 74 percent / PBr3, pyridine / diethyl ether / 1a) overnight, 2) reflux, 2 h
3: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h
4: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C
5: 54 percent / lithium aluminium monoethoxy hydride / diethyl ether
View Scheme
参考文献
Vig, O. P.; Sharma, M. L.; Kumari, Sarla; Rani, Veena
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985 , vol. 24, p. 675 - 676
反应条件
1: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h
2: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C
3: 54 percent / lithium aluminium monoethoxy hydride / diethyl ether
View Scheme
参考文献
Vig, O. P.; Sharma, M. L.; Kumari, Sarla; Rani, Veena
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985 , vol. 24, p. 675 - 676
反应条件
1: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C
2: 54 percent / lithium aluminium monoethoxy hydride / diethyl ether
View Scheme
参考文献
Vig, O. P.; Sharma, M. L.; Kumari, Sarla; Rani, Veena
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985 , vol. 24, p. 675 - 676
反应条件
1: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating
2: 83 percent / propionic acid / 1 h / 140 °C
3: LiAlH4 / diethyl ether
View Scheme
参考文献
Chattopadhyay, A.; Mamdapur, V. R.; Chadha, M. S.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987 , vol. 26, # 1-12 p. 187 - 188
反应条件
Yield given. Multistep reaction;
参考文献
Hutzinger, Michael W.; Oehlschlager, Allan C.
Journal of Organic Chemistry, 1995 , vol. 60, # 14 p. 4595 - 4601
