(Z,E)-十三-4,7-二烯-1-基乙酸酯合成路线 （共 53 条）
反应条件
1: 100 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 / 2 h / 25 °C
2: 90 percent / dimethylformamide / 3 h / 60 °C
3: 1.) n-BuLi, HMPA / 1.) THF, hexane, -15 deg C, 30 min, 2.) THF, hexane, -10 deg C, 30 min
4: dimethylaminopyridine (DMAP) / tetrahydrofuran / 0.83 h / -10 - 25 °C
5: NaOH / diethyl ether; methanol / 0.42 h / 25 °C
6: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / Heating
7: 92 percent / pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 50 °C
8: 99 percent / dimethylaminopyridine (DMAP), pyridine / 0.5 h / 25 °C
View Scheme
参考文献
Ivanova, N. M.; Cheskis, B. E.; Moiseenkov, A. M.; Nefedov, O. M.
Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992 , vol. 41, # 10.2 p. 2362 - 2367,1853 - 1857
反应条件
1: 90 percent / dimethylformamide / 3 h / 60 °C
2: 1.) n-BuLi, HMPA / 1.) THF, hexane, -15 deg C, 30 min, 2.) THF, hexane, -10 deg C, 30 min
3: dimethylaminopyridine (DMAP) / tetrahydrofuran / 0.83 h / -10 - 25 °C
4: NaOH / diethyl ether; methanol / 0.42 h / 25 °C
5: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / Heating
6: 92 percent / pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 50 °C
7: 99 percent / dimethylaminopyridine (DMAP), pyridine / 0.5 h / 25 °C
View Scheme
参考文献
Ivanova, N. M.; Cheskis, B. E.; Moiseenkov, A. M.; Nefedov, O. M.
Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992 , vol. 41, # 10.2 p. 2362 - 2367,1853 - 1857
反应条件
1: 92 percent / pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 50 °C
2: 99 percent / dimethylaminopyridine (DMAP), pyridine / 0.5 h / 25 °C
View Scheme
参考文献
Ivanova, N. M.; Cheskis, B. E.; Moiseenkov, A. M.; Nefedov, O. M.
Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992 , vol. 41, # 10.2 p. 2362 - 2367,1853 - 1857
反应条件
1: 1.) n-BuLi, HMPA / 1.) THF, hexane, -15 deg C, 30 min, 2.) THF, hexane, -10 deg C, 30 min
2: dimethylaminopyridine (DMAP) / tetrahydrofuran / 0.83 h / -10 - 25 °C
3: NaOH / diethyl ether; methanol / 0.42 h / 25 °C
4: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / Heating
5: 92 percent / pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 50 °C
6: 99 percent / dimethylaminopyridine (DMAP), pyridine / 0.5 h / 25 °C
View Scheme
参考文献
Ivanova, N. M.; Cheskis, B. E.; Moiseenkov, A. M.; Nefedov, O. M.
Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992 , vol. 41, # 10.2 p. 2362 - 2367,1853 - 1857
反应条件
1: LiNH2 / liquid ammonia
2: PBr3, 2.6-lutidine / diethyl ether
3: n-Bu3SnCl
4: 84 percent / quinoline, H2 / Pd-BaSO4 / methanol
5: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature
6: 74 percent / pyridine / Ambient temperature
7: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C
8: 1) diisobutylaluminium hydride, 2) sodium borohydride
View Scheme
参考文献
Nishiyama, Hisao; Sakuta, Koji; Itoh, Kenji
Tetrahedron Letters, 1984 , vol. 25, # 2 p. 223 - 226
反应条件
1: 1.) C2H5MgBr, 2.) cuprous chloride / 1.) THF, reflux, 3 h, 2.) a). 20 deg C, 2 h, b). 65 deg C, 12 h
2: 98 percent / ammonium sulfate, tert-butyl alcohol, lithium / tetrahydrofuran; liquid ammonia / 2 h
3: 96 percent / pyridine / diethyl ether / 4 h / Ambient temperature
View Scheme
参考文献
Ishchenko, R. I.; Kovalev, B. G.
Journal of Organic Chemistry USSR (English Translation), 1989 , vol. 25, # 2.1 p. 258 - 262
Zhurnal Organicheskoi Khimii, 1989 , vol. 25, # 2 p. 291 - 296
反应条件
1: 89 percent / LiAlH4 / diethyl ether / 2 h / 0 °C
2: 80 percent / pyridine / 12 h / Ambient temperature
View Scheme
参考文献
Odinokov; Vakhidov; Shakhmaev; Zorin
Chemistry of Natural Compounds, 1997 , vol. 33, # 3 p. 350 - 352
反应条件
1: 83 percent / tetrahydrofuran
2: 74 percent / H2 / (methyl benzoate)chromium tricarbonyl / acetone / 3 h / 120 - 125 °C / 45600 Torr
3: 71 percent / propionic acid / toluene / 3 h / Heating
4: 76 percent / LiAlH4 / diethyl ether
5: 88 percent / pyridine
View Scheme
参考文献
Vasil'ev; Serebryakov
Russian Chemical Bulletin, 1996 , vol. 45, # 9 p. 2232 - 2235
反应条件
1: 74 percent / H2 / (methyl benzoate)chromium tricarbonyl / acetone / 3 h / 120 - 125 °C / 45600 Torr
2: 71 percent / propionic acid / toluene / 3 h / Heating
3: 76 percent / LiAlH4 / diethyl ether
4: 88 percent / pyridine
View Scheme
参考文献
Vasil'ev; Serebryakov
Russian Chemical Bulletin, 1996 , vol. 45, # 9 p. 2232 - 2235
反应条件
1: 78 percent / conc. HCl / methanol / 4 h
2: 1.) H2, 2.) PBr3 / 1.) NIP-2 / 2.) ether, reflux, 4 h
3: 1.) EtMgBr, 2.) CuCN, HMPT / 1.) THF, RT, 2 h, 2.) THF, 3 h
4: 79 percent / conc. H2SO4 / CCl4 / 10 h
5: LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 20 h / 145 - 150 °C
6: 88 percent / pyridine / 24 h / Ambient temperature
View Scheme
参考文献
Gocan, Alexandra; Gansca, Lucia; Oprean, Ioan
Revue Roumaine de Chimie, 1995 , vol. 40, # 3 p. 253 - 258
