(3E,13Z)-十八碳二烯-1-基乙酸酯合成路线 （共 61 条）
反应条件
1: 82 percent / NaI / acetone / 48 h / Heating
2: 66 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -50 °C
3: 84 percent / p-TsOH / methanol / 16 h / 20 °C
4: 97 percent / Na(Hg); Na2HPO4 / methanol / 21 h / 20 °C
5: 83 percent / Na; NH3 / tetrahydrofuran / 4 h
6: 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
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
反应条件
1: 84 percent / p-TsOH / methanol / 16 h / 20 °C
2: 97 percent / Na(Hg); Na2HPO4 / methanol / 21 h / 20 °C
3: 83 percent / Na; NH3 / tetrahydrofuran / 4 h
4: 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
反应条件
1: 97 percent / Na(Hg); Na2HPO4 / methanol / 21 h / 20 °C
2: 83 percent / Na; NH3 / tetrahydrofuran / 4 h
3: 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
反应条件
1.1: BuLi / tetrahydrofuran / 0.5 h / 20 °C
1.2: 33 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 20 °C
2.1: 82 percent / NaI / acetone / 48 h / Heating
3.1: 66 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -50 °C
4.1: 84 percent / p-TsOH / methanol / 16 h / 20 °C
5.1: 97 percent / Na(Hg); Na2HPO4 / methanol / 21 h / 20 °C
6.1: 83 percent / Na; NH3 / tetrahydrofuran / 4 h
7.1: 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
反应条件
1: tetrahydrofuran / 0.33 h / 20 °C
2: LiBr / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Heating
3: 81 percent / dimethylformamide / 4 h / 110 °C
4: 66 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -50 °C
5: 84 percent / p-TsOH / methanol / 16 h / 20 °C
6: 97 percent / Na(Hg); Na2HPO4 / methanol / 21 h / 20 °C
7: 83 percent / Na; NH3 / tetrahydrofuran / 4 h
8: 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
反应条件
1: H2, 1,2-diaminoethane / P2-Ni / ethanol
2: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h
3: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h
4: Dowex W-50 (H+ form) / methanol / 16 h
5: 66 percent / sodium, 1,2-ethanediol / toluene / 2 h / 98 - 100 °C
6: pyridine
View Scheme
参考文献
Hoskovec, Michal; Saman, David; Koutek, Bohumir
Collection of Czechoslovak Chemical Communications, 1990 , vol. 55, # 9 p. 2270 - 2281
反应条件
1: 85 percent / p-TsOH / diethyl ether / 5 h / 0 - 3 °C
2: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h
3: Dowex W-50 (H+ form) / methanol / 20 h
4: H2, 1,2-diaminoethane / P2-Ni / ethanol
5: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h
6: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h
7: Dowex W-50 (H+ form) / methanol / 16 h
8: 66 percent / sodium, 1,2-ethanediol / toluene / 2 h / 98 - 100 °C
9: pyridine
View Scheme
参考文献
Hoskovec, Michal; Saman, David; Koutek, Bohumir
Collection of Czechoslovak Chemical Communications, 1990 , vol. 55, # 9 p. 2270 - 2281
反应条件
1: 1.) LiNH2 / 1.) THF, 1.5 h, 2.) 4 h
2: Dowex W-50 (H+ form) / methanol / 20 h
3: H2, 1,2-diaminoethane / P2-Ni / ethanol
4: 89 percent / PPh3, CBr4 / CH2Cl2 / 1.) from 0 deg C to 20 deg C, 1 h, 2) 20 deg C, 14 h
5: 1.) butyllithium, HMPA, 2.) HMPA / 1.) THF, hexane, -20 deg C, 1 h, 2.) RT, 4 h
6: Dowex W-50 (H+ form) / methanol / 16 h
7: 66 percent / sodium, 1,2-ethanediol / toluene / 2 h / 98 - 100 °C
8: pyridine
View Scheme
参考文献
Hoskovec, Michal; Saman, David; Koutek, Bohumir
Collection of Czechoslovak Chemical Communications, 1990 , vol. 55, # 9 p. 2270 - 2281
反应条件
1: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C
2: 58 percent / LAH / bis-(2-methoxy-ethyl) ether / 48 h / Heating
3: 81 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature
View Scheme
参考文献
Singh, Vasundhara; Trehan, I. R.; Kad, G. L.
Journal of the Indian Chemical Society, 1992 , vol. 69, # 2 p. 103 - 105
