(2E,6E,10E)-1-溴-3,7,11,15-四甲基-2,6,10,14-十六碳四烯合成路线 （共 35 条）
反应条件
1: potassium hydroxide; water / methanol / 80 °C
2: sodium hydride / tetrahydrofuran / 41 h / -30 - 20 °C
3: lithium aluminium tetrahydride / tetrahydrofuran / 1.25 h / 0 - 20 °C
4: phosphorus tribromide / diethyl ether / 0 °C
View Scheme
参考文献
COYOTE PHARMACEUTICALS, INC.; BARRES, Ben A.; NAKAYAMA, Naoki; SERIZAWA, Hiroaki; ARGADE, Ankush B.
Patent: WO2012/31028 A2, 2012 ;
反应条件
1: lithium aluminium tetrahydride / tetrahydrofuran / 1.25 h / 0 - 20 °C
2: phosphorus tribromide / diethyl ether / 0 °C
View Scheme
参考文献
COYOTE PHARMACEUTICALS, INC.; BARRES, Ben A.; NAKAYAMA, Naoki; SERIZAWA, Hiroaki; ARGADE, Ankush B.
Patent: WO2012/31028 A2, 2012 ;
反应条件
1: K2CO3 / methanol / 20 °C
2: PBr3 / diethyl ether / 3 h / 0 °C
View Scheme
参考文献
Bakkestuen, Anne Kristin; Gundersen, Lise-Lotte; Petersen, Dirk; Utenova, Bibigul T.; Vik, Anders
Organic and Biomolecular Chemistry, 2005 , vol. 3, # 6 p. 1025 - 1033
反应条件
1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating
2: 72 percent / NaBH4 / methanol / 5 h / -10 °C
3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
5: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
6: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
View Scheme
参考文献
Sato, Kikumasa; Inoue, Seiichi; Onishi, Akira; Uchida, Nobuhiko; Minowa, Nobuto
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981 , p. 761 - 769
反应条件
1: 72 percent / NaBH4 / methanol / 5 h / -10 °C
2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
4: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
5: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
View Scheme
参考文献
Sato, Kikumasa; Inoue, Seiichi; Onishi, Akira; Uchida, Nobuhiko; Minowa, Nobuto
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981 , p. 761 - 769
反应条件
1: lithium aluminium hydride
2: phosphorus tribromide
View Scheme
参考文献
Suga, Takayuki; Shishibori, Tsuyoshi
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 2098 - 2104
反应条件
pyridine; phosphorus tribromide
T=-15°C;
参考文献
Ruzicka; Firmenich
Helvetica Chimica Acta, 1939 , vol. 22, p. 395
反应条件
1: 95.6 percent / Li, EtNH2 / tetrahydrofuran / 0.25 h / -60 °C
2: PBr3 / dimethylformamide / 0.25 h / -10 - -7 °C
View Scheme
参考文献
Fukuda; Kobayashi; Yukimasa; et al.
Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 11 p. 3530 - 3535
反应条件
1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
View Scheme
参考文献
Sato, Kikumasa; Inoue, Seiichi; Onishi, Akira; Uchida, Nobuhiko; Minowa, Nobuto
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981 , p. 761 - 769
反应条件
1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C
2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h
3: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C
4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C
View Scheme
参考文献
Sato, Kikumasa; Inoue, Seiichi; Onishi, Akira; Uchida, Nobuhiko; Minowa, Nobuto
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981 , p. 761 - 769
