(2E,4E,8Z,10E)-N-(2-甲基丙基)-2,4,8,10-十二碳四烯酰胺合成路线 （共 13 条）
反应条件
n-butyllithium in tetrahydrofuran; dimethyl sulfoxide
T=0°C; Yield given. Yields of byproduct given;
参考文献
Crombie, Leslie; Fisher, David
Tetrahedron Letters, 1985 , vol. 26, # 20 p. 2481 - 2484
反应条件
1: 2-N-iso-butyl-2-oxoethyl phosphonium chloride With potassium tert-butylate in tetrahydrofuran
T=20°C; Wittig reaction; 0.5 h;
2: C10H14O in tetrahydrofuran
T=0°C; Wittig reaction; 2 h;
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
2.2: -78 - 20 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
3.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
1.2: -78 - 20 °C
2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
2.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1.1: sodium hydroxide / toluene / 0.42 h / Reflux
2.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
3.2: -78 - 20 °C
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
4.2: -78 °C
5.1: diisobutylaluminium hydride / diethyl ether / 0 °C
6.1: morpholine; palladium(II) chloride bis(benzonitrile) complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
7.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
8.2: -78 - 20 °C
9.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
9.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
2.2: -78 - 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
3.2: -78 °C
4.1: diisobutylaluminium hydride / diethyl ether / 0 °C
5.1: morpholine; palladium(II) chloride bis(benzonitrile) complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
6.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
7.2: -78 - 20 °C
8.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
8.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
1.2: -78 °C
2.1: diisobutylaluminium hydride / diethyl ether / 0 °C
3.1: morpholine; palladium(II) chloride bis(benzonitrile) complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
4.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
5.2: -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
6.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1.1: sodium hydroxide / toluene / 0.42 h / Reflux
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
2.2: -78 - 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
3.2: -78 °C
4.1: diisobutylaluminium hydride / diethyl ether / 0 °C
5.1: morpholine; palladium(II) chloride bis(benzonitrile) complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
6.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
7.2: -78 - 20 °C
8.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
8.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1.1: sodium hydride / diethyl ether; mineral oil / 0 °C
1.2: 0 °C
2.1: diisobutylaluminium hydride / diethyl ether / 0 °C
3.1: morpholine; palladium(II) chloride bis(benzonitrile) complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
4.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
5.2: -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
6.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
反应条件
1.1: morpholine; palladium(II) chloride bis(benzonitrile) complex; copper(l) chloride / tetrahydrofuran / 0 - 20 °C
2.1: naphthalene; lithium; zinc(II) chloride / tetrahydrofuran; methanol / 50 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - -10 °C
3.2: -78 - 20 °C
4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
4.2: 2 h / 0 °C
View Scheme
参考文献
Matovic, Nicholas J.; Hayes, Patricia Y.; Penman, Kerry; Lehmann, Reginald P.; De Voss, James J.
Journal of Organic Chemistry, 2011 , vol. 76, # 11 p. 4467 - 4481
