18-甲基-11-亚甲基雌甾-4-烯-3,17-二酮合成路线 （共 26 条）
反应条件
1: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 2: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 4: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C 5: 72 percent / n-C4H9Br, Li / tetrahydrofuran; diethyl ether / 1.) -10 deg C, 2 h; -5 deg C, 3 h, 2.) -5 deg C, 3 h View Scheme
参考文献
Organic Preparations and Procedures International, , vol. 29, # 5 p. 572 - 576
反应条件
1: 98 percent / BF3*Et2O / methanol / 2.5 h / 0 - 5 °C 2: 100 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 94 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h / -50 - -45 °C 4: 82 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C View Scheme
参考文献
Schering Aktiengesellschaft
Patent: US5140106 A1, 1992 ;
反应条件
hydrogenchloride in methanol; water
T=0°C; Peterson Olefination; 3 h; Reflux;
参考文献
Nickisch, Klaus; Santhamma, Bindu
Patent: US2013/123523 A1, 2013 ;
Location in patent: Page/Page column 0071; 0072; 0073; 0074; 0075 ;
反应条件
Dess-Martin periodane in dichloromethane
T=20°C; 1.33333 h;
参考文献
Tietze, Lutz F.; Krimmelbein, Ilga K.
Chemistry - A European Journal, 2008 , vol. 14, # 5 p. 1541 - 1551
反应条件
toluene-4-sulfonic acid in formic acid
T=50 - 60°C; 7 h;
参考文献
Gao, Hongwu; Su, Xiangdong; Zhou, Liming; Li, Zhensu
Organic Preparations and Procedures International, 1997 , vol. 29, # 5 p. 572 - 576
反应条件
hydrogenchloride
5 h; Ambient temperature;
参考文献
Gao, Hongwu; Su, Xiangdong; Huang, Lei; Li, Zhensu
Synthetic Communications, 1997 , vol. 27, # 11 p. 1981 - 1987
反应条件
formic acid; toluene-4-sulfonic acid
T=50 - 60°C; 7 h;
参考文献
Gao, Hongwu; Su, Xiangdong; Li, Zhensu
Steroids, 1997 , vol. 62, # 5 p. 398 - 402
反应条件
1: 94 percent / Jones' reagent / acetone / 0.25 h / -15 - -10 °C
2: 79 percent / HC(OEt)3, p-TsOH*H2O / CH2Cl2 / 7 h / Heating
3: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C
4: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C
View Scheme
参考文献
Gao, Hongwu; Su, Xiangdong; Zhou, Liming; Li, Zhensu
Organic Preparations and Procedures International, 1997 , vol. 29, # 5 p. 572 - 576
反应条件
1: 79 percent / HC(OEt)3, p-TsOH*H2O / CH2Cl2 / 7 h / Heating
2: 88 percent / benzene; diethyl ether / 3 h / 10 - 15 °C
3: 74 percent / p-TsOH*H2O / formic acid / 7 h / 50 - 60 °C
View Scheme
参考文献
Gao, Hongwu; Su, Xiangdong; Zhou, Liming; Li, Zhensu
Organic Preparations and Procedures International, 1997 , vol. 29, # 5 p. 572 - 576
反应条件
1: 64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature
2: 98 percent / benzene; diethyl ether / 3 h / 10 - 15 °C
3: 76 percent / Li, liq. NH3, t-BuOH / tetrahydrofuran / 0.5 h / -55 - -50 °C
4: 92 percent / aq. HCl / acetone / 1 h / 25 °C
5: 91 percent / CrO3, H2SO4 / acetone / 0.17 h / 0 - 5 °C
6: 80.3 percent / TsOH*H2O, formic acid / 7 h / 50 - 60 °C
View Scheme
参考文献
Gao, Hongwu; Su, Xiangdong; Li, Zhensu
Steroids, 1997 , vol. 62, # 5 p. 398 - 402
