(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: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature
2: 74 percent / pyridine / Ambient temperature
3: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C
4: 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: 84 percent / quinoline, H2 / Pd-BaSO4 / methanol
2: sodium acetate, hydroxylamine hydrochloride / ethanol / Ambient temperature
3: 74 percent / pyridine / Ambient temperature
4: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C
5: 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: 74 percent / pyridine / Ambient temperature
2: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C
3: 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: 79 percent / TMSOTf / CH2Cl2 / 2.5 h / 0 °C
2: 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
pyridine; 4-(N,N-dimethlyamino)pyridine in dichloromethane
0.5 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
参考文献
Nonshita, Katsumasa; Banno, Hiroshi; Maruoka, Keiji; Yamamoto, Hishashi
Journal of the American Chemical Society, 1990 , vol. 112, # 1 p. 316 - 322
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: 68 percent / propionic acid / 2 h / 136 - 139 °C
2: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature
3: 89 percent / LiAlH4 / diethyl ether / 2 h / 0 °C
4: 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: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature
2: 89 percent / LiAlH4 / diethyl ether / 2 h / 0 °C
3: 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: LiAlH4 / diethyl ether / 0.33 h / 0 °C
2: ZnBr2, Me3SiBr / CH2Cl2 / 0.5 h / -10 °C
3: 100 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 / 2 h / 25 °C
4: 90 percent / dimethylformamide / 3 h / 60 °C
5: 1.) n-BuLi, HMPA / 1.) THF, hexane, -15 deg C, 30 min, 2.) THF, hexane, -10 deg C, 30 min
6: dimethylaminopyridine (DMAP) / tetrahydrofuran / 0.83 h / -10 - 25 °C
7: NaOH / diethyl ether; methanol / 0.42 h / 25 °C
8: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / Heating
9: 92 percent / pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 50 °C
10: 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: ZnBr2, Me3SiBr / CH2Cl2 / 0.5 h / -10 °C
2: 100 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 / 2 h / 25 °C
3: 90 percent / dimethylformamide / 3 h / 60 °C
4: 1.) n-BuLi, HMPA / 1.) THF, hexane, -15 deg C, 30 min, 2.) THF, hexane, -10 deg C, 30 min
5: dimethylaminopyridine (DMAP) / tetrahydrofuran / 0.83 h / -10 - 25 °C
6: NaOH / diethyl ether; methanol / 0.42 h / 25 °C
7: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / Heating
8: 92 percent / pyridinium p-toluenesulfonate (PPTS) / methanol / 2 h / 50 °C
9: 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
