(7Z,9e)-7,9-乙酸十二二烯酯合成路线 （共 87 条）
反应条件
1: (i) TsCl, (ii) LiBr, THF
2: (i) Li2CuCl4, (ii) TsOH, aq. MeOH
3: H2 / Lindlar catalyst / methanol
4: pyridine / Ambient temperature
View Scheme
参考文献
Descoins,C. et al.
Bulletin de la Societe Chimique de France, 1977 , p. 941 - 946
反应条件
1: tetrahydrofuran / 2 h / 20 °C
2: dilithium tetrachlorocuprate / tetrahydrofuran / 20 °C
3: acetic acid
View Scheme
参考文献
Diego, Dennis G.; Cunha, Rodrigo L.O.R.; Comasseto, Joao V.
Tetrahedron Letters, 2006 , vol. 47, # 40 p. 7147 - 7148
反应条件
1: dilithium tetrachlorocuprate / tetrahydrofuran / 20 °C
2: acetic acid
View Scheme
参考文献
Diego, Dennis G.; Cunha, Rodrigo L.O.R.; Comasseto, Joao V.
Tetrahedron Letters, 2006 , vol. 47, # 40 p. 7147 - 7148
反应条件
1: 74 percent / H2, NEt3 / 5percent Pd/CaCO3 / tetrahydrofuran
2: 58 percent / PBr3, NEt3 / diethyl ether / a) -30 deg C, 1 h, b) 0 deg C, 1 h
3: 80 percent / methanol / 72 h / Ambient temperature
5: 1) Na/Hg, 2) pyridine, HOAc / 1) MeOH, EtOAc, -35 deg C, 5 h, 2) 0 deg C, overnight
View Scheme
参考文献
Kulkarni, S. M.; Mamdapur, V. R.; Chadha, M. S.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984 , vol. 23, # 12 p. 1208 - 1210
反应条件
1: TsOH / methanol
2: DMAP / diethyl ether
View Scheme
参考文献
Chrelashvili, Z. G.; Mavrov, M. V.; Dolidze, A. V.; Voronkov, A. P.; Serebryakov, E. P.
Russian Chemical Bulletin, 1993 , vol. 42, # 4 p. 734 - 736
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993 , # 4 p. 766 - 768
反应条件
iron(III) chloride in diethyl ether
Ambient temperature; Yield given;
参考文献
Alexakis, A.; Gardette, M.; Colin, S.
Tetrahedron Letters, 1988 , vol. 29, # 24 p. 2951 - 2954
反应条件
1.1: 75 percent / sodium borohydride / ethanol / 3 h / 20 °C
2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C
2.2: tetrahydrofuran / 24 h / 20 °C
3.1: tetrahydrofuran / 2 h / 20 °C
4.1: dilithium tetrachlorocuprate / tetrahydrofuran / 20 °C
5.1: acetic acid
View Scheme
参考文献
Diego, Dennis G.; Cunha, Rodrigo L.O.R.; Comasseto, Joao V.
Tetrahedron Letters, 2006 , vol. 47, # 40 p. 7147 - 7148
反应条件
1: 60 percent / Zn(Cu) / propan-2-ol; H2O / 4 h / 130 - 140 °C
2: 80 percent / KOH / diethyl ether / 1.5 h / -20 to room temperature
3: 87 percent / LiBr / dimethylformamide / 1.) 50 deg C, 2 h, 2.) 20 - 25 deg C, 12 h
4: 85 percent / Mg, Li2CuCl4 / tetrahydrofuran / -20 °C
5: FeCl3 / diethyl ether / 20 °C
View Scheme
参考文献
Chrelashvili, Z. G.; Mavrov, M. V.; Ugrak, B. I.; Kutin, A. A.; Serebryakov, E. P.
Russian Chemical Bulletin, 1993 , vol. 42, # 9 p. 1593 - 1597
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993 , # 9 p. 1656 - 1660
反应条件
1: 56 percent / Zn(Cu) / propan-2-ol; H2O / 4 h / 85 - 90 °C
2: 92 percent / triethylamine, 4-dimethylaminopyridine / diethyl ether / 30 h / 20 °C
3: 45 percent / Mg, Li2CuCl4 / tetrahydrofuran / -20 °C
4: FeCl3 / diethyl ether / 20 °C
View Scheme
参考文献
Chrelashvili, Z. G.; Mavrov, M. V.; Ugrak, B. I.; Kutin, A. A.; Serebryakov, E. P.
Russian Chemical Bulletin, 1993 , vol. 42, # 9 p. 1593 - 1597
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993 , # 9 p. 1656 - 1660
反应条件
1.1: 0.2 g / PCC / CH2Cl2 / 2 h / 10 - 15 °C
2.1: Mg; I2 / diethyl ether
2.2: 70 percent / CH2Cl2; diethyl ether / 15 h / 20 °C
3.1: Et3N / CH2Cl2 / 2 h / 0 °C
4.1: 0.14 g / LiAlH4 / CH2Cl2 / 4 h / 0 °C
5.1: 9-BBN / tetrahydrofuran / 2 h / 10 °C
5.2: 0.14 g / aq. NaOH; H2O2 / tetrahydrofuran / 2 h / 25 °C
6.1: 1.63 g / pyridine / 24 h / 20 °C
View Scheme
参考文献
Kukovinets; Kasradze; Chernukha; Odinokov; Galin; Abdullin; Fedorov; Tolstikov
Russian Journal of Organic Chemistry, 2000 , vol. 36, # 2 p. 211 - 213
