2,2-二甲基-4-戊烯醛合成路线 （共 65 条）
反应条件
1: 91 percent / Mg / diethyl ether
2: 85 percent / H2CrO4 / H2O; diethyl ether
3: 79 percent / p-TsOH*H2O / benzene / 48 h / Heating
4: 4.28 g / BH3-Me2S / tetrahydrofuran
5: pyridine
6: 85 percent / Li2CuCl4 / tetrahydrofuran
8: 97 percent / p-TsOH*H2O / benzene
9: 1) i-Pr2NLi / 1) THF, -78 degC; 2) THF
10: 45 percent / TiCl2(Oi-Pr)2 / CH2Cl2 / 20 h / -78 - 25 °C
View Scheme
参考文献
Cockerill, Stuart G.; Kocienski, Philip; Treadgold, Richard
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985 , p. 2101 - 2108
反应条件
AgBr; manganese in tetrahydrofuran
T=20°C; 40 h; Darkness;
参考文献
Barczak, Nicholas T.; Jarvo, Elizabeth R.
European Journal of Organic Chemistry, 2008 , # 33 p. 5507 - 5510
参考文献
Tiecco, Marcello; Testaferri, Lorenzo; Bagnoli, Luana
Tetrahedron, 1996 , vol. 52, # 19 p. 6811 - 6822
反应条件
N-bromosuccinmide in dimethyl sulfoxide
T=20°C; 3 h;
参考文献
Gulla, Mahendra; Bierer, Lars; Schmidt, Stefan; Redcliffe, Leo; Jaeger, Volker
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2006 , vol. 61, # 4 p. 471 - 485
反应条件
1.1: 72 percent / NaBH4; aq. NaOH / ethanol / 20 °C
2.1: 91 percent Spectr. / CBr4; PPh3 / acetonitrile / Heating
3.1: disiamylborane / tetrahydrofuran / 0 °C
3.2: 62 percent / NaOH; aq. H2O2 / tetrahydrofuran / 20 °C
4.1: 75 percent / pyridinium dichromate / CH2Cl2 / 20 °C
5.1: 75 percent / 2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate / benzene / 24 h / Heating
6.1: 67 percent / Ph3SnH; AIBN / benzene-d6 / 5.5 h / 45 °C
7.1: DOWEX 50W; H2O / tetrahydrofuran / 24 h / 20 °C
View Scheme
参考文献
Andersen, Rosaleen J.; Ashwell, Susan; Garnett, Ian; Golding, Bernard T.
Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 24 p. 4488 - 4498
反应条件
1: 92 percent / piperidine, glacial acetic acid / CHCl3 / 14 h / Heating
2: 90 percent / sodium borohydride / ethanol / 0.67 h / 15 - 20 °C
3: 55 percent / Cu, pyridine / methanol / 36 h / Heating
4: 88 percent / lithium aluminium hydride / diethyl ether / Heating
5: 92 percent / pydidinum chlorochromate, celite, sodium acetate / CH2Cl2 / 5 h
6: 96 percent / diethyl ether; tetrahydrofuran / -60 °C
7: 95 percent / MnO2 / CHCl3 / 72 h / Ambient temperature
8: 97 percent / potassium t-butoxide / diethyl ether / 16 h / 1.) ether, 16 h
9: 87 percent / NaCl, water / dimethylsulfoxide / 10 h / 150 °C
10: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C
View Scheme
参考文献
Pattenden; Teague
Tetrahedron, 1987 , vol. 43, # 23 p. 5637 - 5652
反应条件
1: lithium aluminium tetrahydride / diethyl ether / Reflux
2: 1H-imidazole / tetrahydrofuran / 20 h / 20 °C
View Scheme
参考文献
Horiuchi, Takao; Takeda, Yasuyuki; Haginoya, Noriyasu; Miyazaki, Masaki; Nagata, Motoko; Kitagawa, Mayumi; Akahane, Kouichi; Uoto, Kouichi
Chemical and Pharmaceutical Bulletin, 2011 , vol. 59, # 8 p. 991 - 1002
反应条件
2: O2; MS3A; pyridine / Pd(OAc)2 / toluene / 2 h / 80 °C
View Scheme
参考文献
Nishimura, Takahiro; Onoue, Tomoaki; Ohe, Kouichi; Uemura, Sakae
Journal of Organic Chemistry, 1999 , vol. 64, # 18 p. 6750 - 6755
反应条件
1.1: 79 percent / Li / tetrahydrofuran / 0.75 h
2.1: 89 percent / PCC; silica gel / CH2Cl2 / 2 h
3.1: 80 percent / tetrahydrofuran / 4 h
4.1: 76 percent / PCC; silica gel / CH2Cl2 / 24 h
5.1: 81 percent / NaBH4 / methanol / 0 - 5 °C
6.1: 45 percent / EtCOOH / 48 h / 180 °C
7.1: 94 percent / PhCH=RuCl2(PCy3)2 / CH2Cl2 / 10 h / 20 °C
8.1: 99 percent / H2 / Pd/C / ethanol / 6 h
9.1: LAH / diethyl ether / 1 h / 0 - 5 °C
9.2: PCC; silica gel / CH2Cl2 / 0.5 h
10.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C
View Scheme
参考文献
Srikrishna; Satyanarayana
Tetrahedron Letters, 2003 , vol. 44, # 5 p. 1027 - 1030
反应条件
oxygen; copper(l) chloride; palladium dichloride in water; N,N-dimethyl-formamide
1 h; Ambient temperature;
参考文献
Magnus, P. D.; Nobbs, M. S.
Synthetic Communications, 1980 , vol. 10, # 4 p. 273 - 278
