(9Z)-9-十六碳烯-1-醇合成路线 （共 46 条）
反应条件
1: 91 percent / triethylamine / CH2Cl2 / 0.5 h / 0 °C
2: 90 percent / LAH / 1.) ether, 1h, reflux, 2.) rt
3: Br2, / CCl4
4: 74 percent / NaNH2, NH3 / tetrahydrofuran / 2 h
5: 97 percent / H2 / ethylendiamine poisoned P-2 Ni / ethanol
View Scheme
参考文献
Chattopadhyay, S.; Mamdapur, V. R.; Chadha, M. S.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984 , vol. 23, # 3 p. 236 - 237
反应条件
1: p-TsOH / methanol
2: 86 percent / H2 / P2Ni
View Scheme
参考文献
Mithran, S.; Mamdapur, V. R.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989 , vol. 28, # 1-11 p. 755 - 756
反应条件
1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C
1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C
2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C
View Scheme
参考文献
Sarkar; Prasad; Nandy, Sonia
Journal of the Indian Chemical Society, 2005 , vol. 82, # 5 p. 475 - 476
反应条件
1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C
1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C
2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C
View Scheme
参考文献
Sarkar; Prasad; Nandy, Sonia
Journal of the Indian Chemical Society, 2005 , vol. 82, # 5 p. 475 - 476
反应条件
1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, from 50 to 55 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) 20 deg C, 12 h
2: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C
View Scheme
参考文献
Dzhumakulov, T.; Kadyrova, M. M.
Chemistry of Natural Compounds, 1992 , vol. 28, # 2 p. 240 - 241
Khimiya Prirodnykh Soedinenii, 1992 , # 2 p. 276 - 277
反应条件
1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C
2: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature
3: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h
4: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C
View Scheme
参考文献
Odinokov, V. N.; Galeeva, R. I.; Ishmuratov, G. Yu.; Kargapol'tseva, T. A.; Sokol'skaya, O. V.; et al.
Journal of Organic Chemistry USSR (English Translation), 1990 , vol. 26, # 11 p. 1986 - 1989
Zhurnal Organicheskoi Khimii, 1990 , vol. 26, # 11 p. 2299 - 2303
反应条件
1: 63 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) RT, 15 h
2: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature
3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C
4: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature
5: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h
6: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C
View Scheme
参考文献
Odinokov, V. N.; Galeeva, R. I.; Ishmuratov, G. Yu.; Kargapol'tseva, T. A.; Sokol'skaya, O. V.; et al.
Journal of Organic Chemistry USSR (English Translation), 1990 , vol. 26, # 11 p. 1986 - 1989
Zhurnal Organicheskoi Khimii, 1990 , vol. 26, # 11 p. 2299 - 2303
反应条件
1: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature
2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C
3: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature
4: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h
5: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C
View Scheme
参考文献
Odinokov, V. N.; Galeeva, R. I.; Ishmuratov, G. Yu.; Kargapol'tseva, T. A.; Sokol'skaya, O. V.; et al.
Journal of Organic Chemistry USSR (English Translation), 1990 , vol. 26, # 11 p. 1986 - 1989
Zhurnal Organicheskoi Khimii, 1990 , vol. 26, # 11 p. 2299 - 2303
反应条件
1: 87 percent / NH3
2: 1) 9-BBN, 2) H2O2, AcONa
3: 88 percent / H2 / Ni-P2
View Scheme
参考文献
Ishmuratov; Ishmuratova; Odinokov; Tolstikov
Chemistry of Natural Compounds, 1997 , vol. 33, # 1 p. 25 - 30
反应条件
1: 87 percent / NH3
2: 1) 9-BBN, 2) H2O2, AcONa
3: 88 percent / H2 / Ni-P2
View Scheme
参考文献
Ishmuratov; Ishmuratova; Odinokov; Tolstikov
Chemistry of Natural Compounds, 1997 , vol. 33, # 1 p. 25 - 30
