2-[(Z)-2-戊烯基]环戊烯-1-酮合成路线 （共 38 条）
反应条件
1: 1.) LiNEt2 / 1.) HMPT, benzene, THF, -45 deg C, 1.5 h, 2.) -45 deg C, 30 min; room temp., overnight
2: 10percent aq. HCl / hexamethylphosphoric acid triamide; benzene; tetrahydrofuran / 11.5 h / Heating
3: 1.) O3, 2.) H2, quinoline / 2.) Lindlar catalyst / 1.) MeOH, -60 deg C, 2.) 1 atm
4: 87 percent / 1percent aq. NaOH / diethyl ether / 24 h / Ambient temperature
View Scheme
参考文献
Geraghty, Niall W. A.; Morris, Noreen M.
Synthesis, 1989 , # 8 p. 603 - 607
反应条件
1: 88 percent / benzene / 17 h / Heating
2: 1.) LiNEt2 / 1.) HMPT, benzene, THF, -45 deg C, 1.5 h, 2.) -45 deg C, 30 min; room temp., overnight
3: 10percent aq. HCl / hexamethylphosphoric acid triamide; benzene; tetrahydrofuran / 11.5 h / Heating
4: 1.) O3, 2.) H2, quinoline / 2.) Lindlar catalyst / 1.) MeOH, -60 deg C, 2.) 1 atm
5: 87 percent / 1percent aq. NaOH / diethyl ether / 24 h / Ambient temperature
View Scheme
参考文献
Geraghty, Niall W. A.; Morris, Noreen M.
Synthesis, 1989 , # 8 p. 603 - 607
反应条件
1: 1.) O3, 2.) H2, quinoline / 2.) Lindlar catalyst / 1.) MeOH, -60 deg C, 2.) 1 atm
2: 87 percent / 1percent aq. NaOH / diethyl ether / 24 h / Ambient temperature
View Scheme
参考文献
Geraghty, Niall W. A.; Morris, Noreen M.
Synthesis, 1989 , # 8 p. 603 - 607
反应条件
1: 85 percent Chromat. / Pd(OAc)2, PPh3 / acetonitrile / 0.5 h / 80 °C / Heating; effect and amount of different catalyst and solvent
2: 95 percent / H2 / Lindlar catalyst / butan-1-ol / 2 h / 760 Torr / Ambient temperature
View Scheme
参考文献
Kataoka, Hideaki; Yamada, Toshiro; Goto, Kuniaki; Tsuji, Jiro
Tetrahedron, 1987 , vol. 43, # 18 p. 4107 - 4112
反应条件
1: pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature
2: 86 percent / KOH / diethyl ether; tetrahydrofuran; H2O / 1.) reflux, 10h, 2.) room temperature, 36 h.
View Scheme
参考文献
Matsuda, Isamu; Murata, Shizuaki; Izumi, Yusuke
Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 237 - 240
反应条件
2: 1) NaH / 1) allylalcohol, mineral oil, 90 deg C, 3 h; 2) 100 deg C, 3-4 h
3: 55 percent Chromat. / Pd(OAc)2, bis(diphenylphosphino)ethane / acetonitrile / Heating
View Scheme
参考文献
Kataoka, Hideaki; Yamada, Toshiro; Goto, Kuniaki; Tsuji, Jiro
Tetrahedron, 1987 , vol. 43, # 18 p. 4107 - 4112
反应条件
1: 1) NaH / 1) allylalcohol, mineral oil, 90 deg C, 3 h; 2) 100 deg C, 3-4 h
2: 55 percent Chromat. / Pd(OAc)2, bis(diphenylphosphino)ethane / acetonitrile / Heating
View Scheme
参考文献
Kataoka, Hideaki; Yamada, Toshiro; Goto, Kuniaki; Tsuji, Jiro
Tetrahedron, 1987 , vol. 43, # 18 p. 4107 - 4112
反应条件
palladium diacetate; 1,2-bis-(diphenylphosphino)ethane in acetonitrile
Heating;
参考文献
Kataoka, Hideaki; Yamada, Toshiro; Goto, Kuniaki; Tsuji, Jiro
Tetrahedron, 1987 , vol. 43, # 18 p. 4107 - 4112
反应条件
1: 71 percent / pyridinium chlorochromate, molecular sieves / CH2Cl2 / 36 h / Ambient temperature
2: 93 percent / methanol / 12 h / Ambient temperature
3: 94 percent / lithium aluminium hydride / tetrahydrofuran / 0.33 h / 0 °C
4: 1.) p-toluenesulfonic acid, paraformaldehyde; 2.) BF3*Et2O / 1.) acetone, water, rt, 4 h; 2.) rt, 15 h
5: 90 percent / 1percent NaOH / diethyl ether; H2O / 72 h
View Scheme
参考文献
Rosini, Goffredo; Ballini, Roberto; Petrini, Marino; Sorrenti, Pietro
Tetrahedron, 1984 , vol. 40, # 19 p. 3809 - 3814
反应条件
1: 93 percent / methanol / 12 h / Ambient temperature
2: 94 percent / lithium aluminium hydride / tetrahydrofuran / 0.33 h / 0 °C
3: 1.) p-toluenesulfonic acid, paraformaldehyde; 2.) BF3*Et2O / 1.) acetone, water, rt, 4 h; 2.) rt, 15 h
4: 90 percent / 1percent NaOH / diethyl ether; H2O / 72 h
View Scheme
参考文献
Rosini, Goffredo; Ballini, Roberto; Petrini, Marino; Sorrenti, Pietro
Tetrahedron, 1984 , vol. 40, # 19 p. 3809 - 3814
