5-雄甾-3-烯-17-酮合成路线 (共 25 条)
反应条件
1: 92 percent / diethyl ether / 5 h / 0 °C 2: 82 percent / POCl3 / pyridine / 8 h / Ambient temperature 3: 92 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 4: 81 percent / iPr2NEt / CH2Cl2 / 7 h / Ambient temperature 5: 59 percent / Na2CO3, MeI / H2O; acetonitrile / 3 h / Heating 6: 1.) HMPA, 15percent w/w n-BuLi / 1.) THF, hexane, -78 deg C, 15 min; 2.) THF, -78 deg C, 10 min; 0 deg C, 30 min; rt, 6 h 7: 2.) ethanethiol, BF3*Et2O / 1.) Methylene Blue / 1.) toluene, 220 deg C, 100 h; 2.) CH2Cl2, rt, 1 h 8: 52 percent / CrO3 / pyridine / 10 h / Ambient temperature View Scheme
参考文献
Ihara, Masataka; Sudow, Izumi; Fukumoto, Keiichiro; Kametani, Tetsuji
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 117 - 124
反应条件
1: 2.) ethanethiol, BF3*Et2O / 1.) Methylene Blue / 1.) toluene, 220 deg C, 100 h; 2.) CH2Cl2, rt, 1 h 2: 52 percent / CrO3 / pyridine / 10 h / Ambient temperature View Scheme
参考文献
Ihara, Masataka; Sudow, Izumi; Fukumoto, Keiichiro; Kametani, Tetsuji
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 117 - 124
反应条件
1: conc. HCl / methanol 2: 52 percent / CrO3, pyridine View Scheme
参考文献
Ihara, Masataka; Sudow, Izumi; Fukumoto, Keiichiro; Kametani, Tetsuji
Journal of Organic Chemistry, 1985 , vol. 50, # 1 p. 144 - 145
反应条件
TAMPS in acetonitrile 4 h; RefluxInert atmosphere; stereoselective reaction;
参考文献
Herrmann, Pavel; Kvicala, Jaroslav; Pouzar, Vladimir; Chodounska, Hana
Collection of Czechoslovak Chemical Communications, 2008 , vol. 73, # 12 p. 1825 - 1834
反应条件
lithium bromide in N,N-dimethyl-formamide T=125°C; 2 h; Inert atmosphere; Overall yield = 91 percent; Overall yield = 1.1 g;
参考文献
Qian, Mingxing; Krishnan, Kathiresan; Kudova, Eva; Li, Ping; Manion, Brad D.; Taylor, Amanda; Elias, George; Akk, Gustav; Evers, Alex S.; Zorumski, Charles F.; Mennerick, Steven; Covey, Douglas F.
Journal of Medicinal Chemistry, 2014 , vol. 57, # 1 p. 171 - 190
反应条件
1: 71.3 percent / pyridine / 20 h / 20 °C 2: 18 percent / 72 h / Heating View Scheme
参考文献
Qian, Mingxing; Krishnan, Kathiresan; Kudova, Eva; Li, Ping; Manion, Brad D.; Taylor, Amanda; Elias, George; Akk, Gustav; Evers, Alex S.; Zorumski, Charles F.; Mennerick, Steven; Covey, Douglas F.
Journal of Medicinal Chemistry, 2014 , vol. 57, # 1 p. 171 - 190
反应条件
TAMPS in acetonitrile 11 h; RefluxInert atmosphere; stereoselective reaction;
参考文献
Herrmann, Pavel; Kvicala, Jaroslav; Pouzar, Vladimir; Chodounska, Hana
Collection of Czechoslovak Chemical Communications, 2008 , vol. 73, # 12 p. 1825 - 1834
反应条件
in methanol 72 h; Heating;
参考文献
Amiranashvili, L. Sh.; Sladkov, V. I.; Lindeman, S. V.; Aleksanyan, M. S.; Struchkov, Yu. T.; Suvorov, N. N.
Journal of Organic Chemistry USSR (English Translation), 1990 , vol. 26, # 5.2 p. 906 - 911
Zhurnal Organicheskoi Khimii, 1990 , vol. 26, # 5 p. 1052 - 1058
反应条件
1: Jone's reagent / acetone / 20 °C 2: acetic acid; zinc / 0.25 h / Reflux View Scheme
参考文献
Varela, Carla; Tavares Da Silva, Elisiario J.; Amaral, Cristina; Correia Da Silva, Georgina; Baptista, Teresa; Alcaro, Stefano; Costa, Giosue; Carvalho, Rui A.; Teixeira, Natercia A. A.; Roleira, Fernanda M. F.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 8 p. 3992 - 4002
参考文献
Varela, Carla; Tavares Da Silva, Elisiario J.; Amaral, Cristina; Correia Da Silva, Georgina; Baptista, Teresa; Alcaro, Stefano; Costa, Giosue; Carvalho, Rui A.; Teixeira, Natercia A. A.; Roleira, Fernanda M. F.
Journal of Medicinal Chemistry, 2012 , vol. 55, # 8 p. 3992 - 4002