3-((8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14, 15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-oxopropanenitrile | 1534363-79-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-((8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14, 15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-oxopropanenitrile
• 英文别名: 3-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-3-oxopropanenitrile
• CAS: 1534363-79-5
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: XWJLPWXJKXFFTF-XUCMERPOSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  492.0±45.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14, 15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-oxopropanenitrile 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以68%的产率得到(8S,9S,10R,13S,14S,17S)-17-(5-amino-1H-pyrazol-3-yl)-10,13-dimethyl-6,7,8,9, 10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
  参考文献：
  名称：

  Synthesis of progesterone derivatives and evaluation of their efficiency as pneumococcal vaccines

  摘要：

  Progesterone (1) was used as a template to develop new anticancer compounds. Ring D modification of 1, through its reaction with active methylene derivatives, gave the condensate derivatives 3a, b. The latter compounds underwent heterocyclization reactions through the reaction with either hydrazine hydrate or phenyl hydrazine to give the pyrazole derivatives 6a-d, respectively. The reaction of 1 with bromine gave the alpha-bromo derivative 7, which in turn reacted with potassium cyanide to yield the cyanoacetyl derivative 8. Compound 8 has been subjected to a series of reactions that produced benzylidene, aryl hydrazine, pyrazole, and pyran derivatives. The newly synthesized products were tested for their efficiency as pneumococcal vaccines and the results were promising.

  DOI：

  10.1007/s00044-013-0894-8
• 作为产物：
  描述：

  potassium cyanide 、 (8S,9S,10R,13S,14S,17S)-17-(2-bromoacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14, 15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one 以 乙醇 、 水 为溶剂， 反应 2.0h， 以58%的产率得到3-((8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14, 15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-oxopropanenitrile
  参考文献：
  名称：

  Synthesis of progesterone derivatives and evaluation of their efficiency as pneumococcal vaccines

  摘要：

  Progesterone (1) was used as a template to develop new anticancer compounds. Ring D modification of 1, through its reaction with active methylene derivatives, gave the condensate derivatives 3a, b. The latter compounds underwent heterocyclization reactions through the reaction with either hydrazine hydrate or phenyl hydrazine to give the pyrazole derivatives 6a-d, respectively. The reaction of 1 with bromine gave the alpha-bromo derivative 7, which in turn reacted with potassium cyanide to yield the cyanoacetyl derivative 8. Compound 8 has been subjected to a series of reactions that produced benzylidene, aryl hydrazine, pyrazole, and pyran derivatives. The newly synthesized products were tested for their efficiency as pneumococcal vaccines and the results were promising.

  DOI：

  10.1007/s00044-013-0894-8