1-溴-8-(四氢吡喃氧基)辛烷合成路线 （共 69 条）
反应条件
1: LiNH2; NH3 2: H2 / Lindlar catalyst / ethanol / 0 °C 3: MnO2 / toluene 4: t-BuOK / tetrahydrofuran 5: p-TsOH / methanol 6: pyridine View Scheme
参考文献
Zhu, Junwei; Ryrholm, Nils; Ljungberg, Hakan; Hansson, Bill S.; Hall, David; Reed, Darwin; Loefstedt, Christer
Journal of Chemical Ecology, 1996 , vol. 22, # 8 p. 1505 - 1526
反应条件
1: 87 percent / ethylenediamine 2: 74 percent / n-BuLi, DMPU / tetrahydrofuran; hexane / 1.) 0 deg C, 2 h, 2.) room temperature, overnight 3: 99 percent / p-TsOH / methanol / 4 h / 60 - 65 °C 4: 84.8 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether / 22 h / 120 - 125 °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: 1.) BuLi / 1.) THF, hexane, 2 h, -20 deg C, 2.) 30 min, -78 degC 2: LiAlH4 / diethyl ether / 1 h / 0 °C 3: p-toluenesulfonic acid / methanol; H2O / 3 h / Heating 4: 72 percent / pyridine / 1 h / Heating View Scheme
参考文献
Canevet; Roeder; Vostrowsky; Bestmann
Chemische Berichte, 1980 , vol. 113, # 3 p. 1115 - 1120
反应条件
1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C 1.2: -20 - 20 °C 2.1: Jone's reagent / acetone / 0 - 4 °C 3.1: sulfuric acid / 20 °C 4.1: hydrogen; ethylenediamine / ethanol; water 5.1: 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine / dimethyl sulfoxide / 20 °C View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
反应条件
1: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.)THF, r. t., 12 h 2: p-TsOH / methanol / 2 h / Heating 3: 95 percent / H2, quinoline / Lindlar catalyst / pentane / 1 h / -10 °C 4: 95 percent / pyridine / diethyl ether View Scheme
参考文献
Michelot, Didier
Synthesis, 1983 , # 2 p. 130 - 134
反应条件
dilithium tetrachlorocuprate; toluene-4-sulfonic acid 1.) THF, room temperature, 12 h, 2.) CH3OH, room temperature, 6 h; Multistep reaction;
参考文献
Nakashima, Hideki; Hirata, Norihiko; Iwamura, Takeru; Yamagiwa, Yoshiro; Kamikawa, Tadao
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994 , # 19 p. 2849 - 2858
反应条件
dilithium tetrachlorocuprate; toluene-4-sulfonic acid
1.) THF, room temperature, 12 h, 2.) CH3OH, room temperature, 6 h; Yield given. Multistep reaction;
参考文献
Nakashima, Hideki; Hirata, Norihiko; Iwamura, Takeru; Yamagiwa, Yoshiro; Kamikawa, Tadao
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994 , # 19 p. 2849 - 2858
反应条件
1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C
1.2: -20 - 20 °C
2.1: Jone's reagent / acetone / 0 - 4 °C
3.1: sulfuric acid / 20 °C
4.1: hydrogen; ethylenediamine / ethanol; water
5.1: 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine / dimethyl sulfoxide / 20 °C
View Scheme
参考文献
Fu, Yu; Weng, Yue; Hong, Wen-Xu; Zhang, Qinghai
Synlett, 2011 , # 6 p. 809 - 812
反应条件
1: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h
2: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C
3: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h
View Scheme
参考文献
Odinolov, V. N.; Dzhemilev, U. M.; Ishmuratov, G. Yu.; Botsman, L. P.; Vostrikova, O. S.; et al.
Chemistry of Natural Compounds, 1987 , vol. 23, p. 242 - 244
Khimiya Prirodnykh Soedinenii, 1987 , # 2 p. 286 - 289
反应条件
1: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.)THF, r. t., 12 h
2: p-TsOH / methanol / 2 h / Heating
3: 90 percent / LiAlH4 / 1,2-dimethoxy-ethane / 48 h / 140 °C
4: 95 percent / pyridine / diethyl ether
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
