1-溴-8-(四氢吡喃氧基)辛烷合成路线 （共 69 条）
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
View Scheme
参考文献
Kamezawa, Makoto; Tachibana, Hojun; Ohtani, Takehiko; Naoshima, Yoshinobu
Bioscience, Biotechnology, and Biochemistry, 1993 , vol. 57, # 11 p. 1962 - 1963
反应条件
1: propargyl alcohol With ferric nitrate; ammonia; lithium in tetrahydrofuran
T=-40°C; Reflux;
2: 2-[(8-Bromooctyl)oxy]tetrahydro-2H-pyran in tetrahydrofuran
2.83333 h; Reflux;
参考文献
Mesaros, Clementina; Gugiu, Bogdan G.; Zhou, Rong; Lee, Seon Hwa; Choi, Jaewoo; Laird, James; Blair, Ian A.; Salomon, Robert G.
Chemical Research in Toxicology, 2010 , vol. 23, # 3 p. 516 - 527
反应条件
1: 70 percent / lithium; liquid ammonia; Fe(NO3)3 / 6 h / -33 °C
2: 80 percent / LiAlH4 / tetrahydrofuran / Heating
View Scheme
参考文献
Ochiai, Masahito; Ukita, Tatsuzo; Fujita, Eiichi
Chemical & Pharmaceutical Bulletin, 1983 , vol. 31, # 5 p. 1641 - 1645
反应条件
1: 1.) lithium amide / 1.) liquid NH3, THF, -33 deg C, 2 h, 2.) 6 h
2: pyridinium chlorochromate (PCC) / CH2Cl2 / 1 h
3: 1.) sodium hydride / 1.) THF, RT, 30 min, 2.) 2 h
4: LAH, ethanol / diethyl ether / 0.5 h / 0 °C
5: H2 / Lindlar's catalyst / hexane; ethanol
6: TEA / CH2Cl2 / 4 h / 0 °C
7: 1.) Mg, 2.) Li2CuCl3 / 1.) THF, 2.) 0 deg C, 3 h
8: 82 percent / PTS / methanol / Ambient temperature
View Scheme
参考文献
Vig; Sharma; Kapur; Thapar; Gupta
Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990 , vol. 29, # 7 p. 606 - 610
反应条件
1: 1.) lithium amide / 1.) liq. ammonia, 2 h, 2.) THF, -33 deg C, 6 h
2: 65 percent / triphenylphosphine, carbon tetrachloride / 6 h / Heating
3: 1.) CuI / 1.) ether, room temperature, 1 h, 2.) THF, 4 h, room temperature
4: 85 percent / PTS acid / methanol / 24 h / Ambient temperature
View Scheme
参考文献
Yadav, J S; Deshpande, Prasad K; Reddy, E Rajarathnam
Synthetic Communications, 1989 , vol. 19, # 1, 2 p. 125 - 134
反应条件
1: 81 percent / hexamethylphosphoric acid triamide / 10 h / 25 - 30 °C
2: 97.5 percent / 10percent HCl / tetrahydrofuran / 10 h / 20 - 25 °C
View Scheme
参考文献
Balezina, G. G.; Ishmuratov, G. Yu.; Odinokov, V. N.; Selimov, F. A.; Dzhemilev, U. M.; Tolstikov, G. A.
Chemistry of Natural Compounds, 1984 , vol. 20, # 3 p. 354 - 357
Khimiya Prirodnykh Soedinenii, 1984 , vol. 20, # 3 p. 378 - 382
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
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: 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
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: n-butyllithium / tetrahydrofuran
1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C
2.1: lithium; ethylamine / 1 h / -5 °C
3.1: p-toluenesulfonic acid / ethanol / 3 h / Heating
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: 91 percent / NaI / acetone
2: 1.) (i-C3H7)2NLi / 1.) THF, n-hexane, room temp., 3 h, 2.) 55 deg C, 12 h
3: 92 percent / Amberlyst H-15 / methanol / 1 h / 45 °C
4: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating
5: MnO2 / CH2Cl2 / 6 h / Ambient temperature
6: 1.) Mg/Hg / 1.) Et2O, 30 min, 2.) room temp., 1 h
View Scheme
参考文献
Cardillo, Giuliana; Orena, Mario; Porzi, Gianni; Sandri, Sergio
Gazzetta Chimica Italiana, 1980 , vol. 110, # 9/10 p. 523 - 526
