3-甲基-2-环己烯-1-酮合成路线 （共 314 条）
反应条件
hydrogenchloride; trimethylsilyl trifluoromethanesulfonate
1.) dichloromethane, 0 deg C to room temperature, 2 h, 2.) dichloromethane, water; Yield given. Multistep reaction;
参考文献
Mori, Ichiro; Kimura, Yoko; Nakano, Toshihito; Matsunaga, Shin-Ichiro; Iwasaki, Genji; Ogawa, Atsuko; Hayakawa, Kenji
Tetrahedron Letters, 1997 , vol. 38, # 20 p. 3543 - 3546
反应条件
hydrogenchloride; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate
1.) dichloromethane, 0 deg C, 30 min, 2.) dichloromethane, 0 deg C, 1 h, 3.) dichloromethane, water, 3 h; Yield given. Multistep reaction. Yields of byproduct given;
参考文献
Mori, Ichiro; Kimura, Yoko; Nakano, Toshihito; Matsunaga, Shin-Ichiro; Iwasaki, Genji; Ogawa, Atsuko; Hayakawa, Kenji
Tetrahedron Letters, 1997 , vol. 38, # 20 p. 3543 - 3546
反应条件
1: 72 percent / AcOH / ethanol / 2.5 h / Heating
2: 1) p-TsOH*H2O / 1) benzene, reflux, 1 h; 2) ether
3: 9.5 g / aq. 5 percent HCl, acetone / 1 h / Heating
4: 13.5 g / p-TsOH*H2O / benzene / 1 h / Heating
5: 1) LiAlH4; 2) EtOAc, water, aq. 4 N NaOH / 1) THF, 1 h; 2) RT, 1 h
6: 99 percent / tri-n-butylphosphine / pyridine / 23 h / 60 °C
7: 1) aq. NaHCO3, 80 percent m-chloroperbenzoic acid; 2) aq. 10 percent Na2S2O3 / 1) RT, CH2Cl2, 1 h
8: 4.63 g / aq. 5 percent HCl, acetone / 1.5 h / Heating
9: p-TsOH*H2O / benzene / 0.5 h / Heating
View Scheme
参考文献
Shibuya, Hirotaka; Tsujii, Shinji; Yamamoto, Yoshio; Miura, Hiromi; Kitagawa, Isao
Chemical and Pharmaceutical Bulletin, 1984 , vol. 32, # 9 p. 3417 - 3427
反应条件
1: 3-methyl-cyclohex-2-en-1-one With lithium diisopropyl amide in tetrahydrofuran
T=-78°C; 0.5 h;
2: ethyl bromoacetate in tetrahydrofuran
T=20°C; 2 h;
参考文献
MERCK SHARP and DOHME LIMITED
Patent: WO2005/13985 A1, 2005 ;
Location in patent: Page/Page column 52-53 ;
WO 2005/013985 A1
反应条件
sodium ethanolate in ethanol
216 h; Ambient temperature;
参考文献
Paquette, Leo A.; Poupart, Marc-Andre
Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4245 - 4253
反应条件
indium; chloro-trimethyl-silane in tetrahydrofuran
T=20°C; Michael addition reaction; 0.5 h;
参考文献
Lee, Phil Ho; Seomoon, Dong; Lee, Kooyeon; Heo, Yunkiu
Journal of Organic Chemistry, 2003 , vol. 68, # 6 p. 2510 - 2513
反应条件
DBN in acetonitrile
T=45°C; P=11250900 Torr; 36 h;
参考文献
Dauben, William G.; Gerdes, John M.
Tetrahedron Letters, 1983 , vol. 24, # 36 p. 3841 - 3844
反应条件
sodium tert-pentoxide in benzene
1 h; Ambient temperature;
参考文献
Tamura, Yasumitsu; Wada, Akimori; Okuyama, Shigehiro; Fukumori, Satoshi; Hayashi, Yoko; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 5 p. 1312 - 1320
反应条件
1: 60 percent / lithium dimethylcuprate / diethyl ether; hexamethylphosphoric acid triamide / 2 h / Ambient temperature
2: 58 percent / NaH (60percent) / tetrahydrofuran / Ambient temperature
3: 73 percent / m-CPBA / CH2Cl2 / Ambient temperature
View Scheme
参考文献
Tamura, Yasumitsu; Wada, Akimori; Okuyama, Shigehiro; Fukumori, Satoshi; Hayashi, Yoko; et al.
Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 5 p. 1312 - 1320
反应条件
t-Bu(Me)Cu(CN)Li2 in diethyl ether
T=-25°C; 0.25 h;
参考文献
Lipshutz, Bruce H.; Wilhelm, Robert S.; Kozlowski, Joseph A.
Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 3938 - 3942
