(3E,13Z)-十八碳二烯-1-基乙酸酯合成路线 （共 61 条）
反应条件
1: H2 / Pd/CaCO3 poisoned with Pb / hexane / 18 h
2: pyridine; DMAP
View Scheme
参考文献
Armstrong-Chong, Rosemary J.; Matthews, Kristopher; Chong, J. Michael
Tetrahedron, 2004 , vol. 60, # 45 p. 10239 - 10244
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C
1.2: tetrahydrofuran; hexane / 1 h / 0 °C
1.3: 58 percent / tetrahydrofuran; hexane / 1 h / 0 °C
2.1: 99 percent / PPTS / diethyl ether / 4 h / 60 °C
3.1: H2 / Pd/CaCO3 poisoned with Pb / hexane / 18 h
4.1: pyridine; DMAP
View Scheme
参考文献
Armstrong-Chong, Rosemary J.; Matthews, Kristopher; Chong, J. Michael
Tetrahedron, 2004 , vol. 60, # 45 p. 10239 - 10244
反应条件
1: 99 percent / PPTS / diethyl ether / 4 h / 60 °C
2: H2 / Pd/CaCO3 poisoned with Pb / hexane / 18 h
3: pyridine; DMAP
View Scheme
参考文献
Armstrong-Chong, Rosemary J.; Matthews, Kristopher; Chong, J. Michael
Tetrahedron, 2004 , vol. 60, # 45 p. 10239 - 10244
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C
1.2: tetrahydrofuran; hexane / 1 h / 0 °C
1.3: 58 percent / tetrahydrofuran; hexane / 1 h / 0 °C
2.1: 99 percent / PPTS / diethyl ether / 4 h / 60 °C
3.1: H2 / Pd/CaCO3 poisoned with Pb / hexane / 18 h
4.1: pyridine; DMAP
View Scheme
参考文献
Armstrong-Chong, Rosemary J.; Matthews, Kristopher; Chong, J. Michael
Tetrahedron, 2004 , vol. 60, # 45 p. 10239 - 10244
反应条件
1: 91 percent / pyridine; DMAP
2: 97 percent / H2 / Pd/CaCO3 poisoned with Pb / hexane / 40 h
View Scheme
参考文献
Armstrong-Chong, Rosemary J.; Matthews, Kristopher; Chong, J. Michael
Tetrahedron, 2004 , vol. 60, # 45 p. 10239 - 10244
反应条件
1: 1.) HMPTA, n-BuLi, 3.) 4-dimethylaminopyridine (DMAP)
2: NaOH / diethyl ether; methanol / 0.33 h / 25 °C
3: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / 80 °C
4: 100 percent / TsOH*pyridine / methanol / 2 h / 50 °C
5: 1.) n-BuLi, Ph3CH, HMPTA, 2.) TsCl, 3.) NaBr
6: 1.) LDA, 2.) SiO2 / 1.) hexane, THF, HMPTA, 0 deg C, 45 min, 2.) hexane, THF, HMPTA. 0-25 deg C
7: 98 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C
8: 100 percent / ZnBr2, Me3SiBr / CH2Cl2 / 0.25 h / -20 °C
9: 89 percent / dibenzo-18-crown-6 (DB-18-C-6) / acetonitrile / 15 h / 80 °C
View Scheme
参考文献
Ivanova, N. M.; Cheskis, B. A.; Moiseenkov, A. M.; Nefedov, O. M.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991 , vol. 40, # 11.1 p. 2196 - 2204
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991 , # 11 p. 2521 - 2529
反应条件
1: 1.) HMPTA, n-BuLi, 3.) 4-dimethylaminopyridine (DMAP)
2: NaOH / diethyl ether; methanol / 0.33 h / 25 °C
3: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / 80 °C
4: 100 percent / TsOH*pyridine / methanol / 2 h / 50 °C
5: 1.) n-BuLi, Ph3CH, HMPTA, 2.) TsCl, 3.) NaBr
6: 1.) LDA, 2.) SiO2 / 1.) hexane, THF, HMPTA, 0 deg C, 45 min, 2.) hexane, THF, HMPTA. 0-25 deg C
7: 98 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C
8: 100 percent / ZnBr2, Me3SiBr / CH2Cl2 / 0.25 h / -20 °C
9: 89 percent / dibenzo-18-crown-6 (DB-18-C-6) / acetonitrile / 15 h / 80 °C
View Scheme
参考文献
Ivanova, N. M.; Cheskis, B. A.; Moiseenkov, A. M.; Nefedov, O. M.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991 , vol. 40, # 11.1 p. 2196 - 2204
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991 , # 11 p. 2521 - 2529
反应条件
1: 100 percent / ZnBr2, Me3SiBr / CH2Cl2 / 0.25 h / -20 °C
2: 89 percent / dibenzo-18-crown-6 (DB-18-C-6) / acetonitrile / 15 h / 80 °C
View Scheme
参考文献
Ivanova, N. M.; Cheskis, B. A.; Moiseenkov, A. M.; Nefedov, O. M.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991 , vol. 40, # 11.1 p. 2196 - 2204
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991 , # 11 p. 2521 - 2529
反应条件
1: 98 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C
2: 100 percent / ZnBr2, Me3SiBr / CH2Cl2 / 0.25 h / -20 °C
3: 89 percent / dibenzo-18-crown-6 (DB-18-C-6) / acetonitrile / 15 h / 80 °C
View Scheme
参考文献
Ivanova, N. M.; Cheskis, B. A.; Moiseenkov, A. M.; Nefedov, O. M.
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991 , vol. 40, # 11.1 p. 2196 - 2204
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991 , # 11 p. 2521 - 2529
反应条件
1: 66 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -50 °C
2: 84 percent / p-TsOH / methanol / 16 h / 20 °C
3: 97 percent / Na(Hg); Na2HPO4 / methanol / 21 h / 20 °C
4: 83 percent / Na; NH3 / tetrahydrofuran / 4 h
5: 95 percent / DMAP; Et3N / CH2Cl2
View Scheme
参考文献
Capdevila, Anna; Prasad, Attaluri R.; Quero, Carmen; Petschen, Ines; Bosch, Maria P.; Guerrero, Angel
Organic Letters, 1999 , vol. 1, # 6 p. 845 - 848
