4-aza-androst-16-en-3-one

• 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: 4-aza-androst-16-en-3-one
• 英文别名: (3aS,3bS,9aR,9bS,11aR)-9a,11a-dimethyl-3,3a,3b,4,5,5a,6,8,9,9b,10,11-dodecahydroindeno[5,4-f]quinolin-7-one
• 化学式: C₁₈H₂₇NO
• 分子量: 273.418
• InChiKey: IZOSXDNFNOUPQL-ZDISZSNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  亚磷酸二异丙酯 、 17-iodo-4-aza-androst-16-en-3-one 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三乙胺 作用下， 反应 20.0h， 以93%的产率得到diisopropyl 4-aza-androst-16-en-3-one-17-phosphonate
  参考文献：
  名称：

  Steroidal alkenylphosphonates via palladium-catalyzed coupling reactions

  摘要：

  The palladium-catalyzed coupling of various 17-iodo-Delta(16) steroids (17-iodo-androst-16-ene, 17-iodo-4-methyl-4-aza-androst-16-en-3-one, and 17-iodo-4-aza-androst-16-en-3-one) with dialkyl phosphites (dimethyl phosphite, diethyl phosphite, and diisopropyl phosphite) was examined in detail. The only successful condition for homogeneous coupling involved carrying out the reaction in the absence of any solvents. A large excess of dialkyl phosphite was used, which means that the phosphite itself acted as a solvent. Eight new androst-16-ene derivatives with phosphonate groups at C-17 were synthesized and characterized. These steroids are of pharmacological interest as potential Sol-reductase inhibitors. Under the same conditions, methylation of lactam NH was observed using dimethyl phosphite.

  DOI：

  10.1016/0039-128x(95)00121-6

文献信息

• Process
  申请人：——

  公开号：US20040049042A1

  公开（公告）日：2004-03-11

  An improved process for preparing steriods, such as 3-oxo-4-azasteroids, is described. Compounds of this type are known to be useful in the preparation of compounds having 5a-reductase inhibitor activity. The process comprises the hydrogenation of the corresponding steroid alkene in the presence of ammonium acetate, ammonium formate, and/or ammonium propionate and an appropriate catalyst.

  本文描述了一种改进的制备类固醇的方法，例如3-氧代-4-氮杂类固醇。这种类型的化合物已知在制备具有5a-还原酶抑制剂活性的化合物方面非常有用。该过程包括在氨醋酸铵、氨甲酸铵和/或氨丙酸铵以及适当的催化剂存在下对相应的类固醇烯烃进行氢化。
• PROCESS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1335930A2

  公开（公告）日：2003-08-20
• Process for the preparation of 3-oxo-4-azasteroids
  申请人：GLAXO GROUP LIMITED

  公开号：EP1335930B1

  公开（公告）日：2004-10-13
• US6794508B2
  申请人：——

  公开号：US6794508B2

  公开（公告）日：2004-09-21
• [EN] PROCESS<br/>[FR] PROCEDE
  申请人：GLAXO GROUP LTD

  公开号：WO2002046207A2

  公开（公告）日：2002-06-13

  An improved process for preparing steroids, such as 3-oxo-4-azasteroids, is described. Compounds of this type are known to be useful in the preparation of compounds having 5a-reductase inhibitor activity. The process comprises the hydrogenation of the corresponding steroid alkene in the presence of ammonium acetate, ammonium formate, and/or ammonium propionate and an appropriate catalyst.