3-oxo-4-aza-5-α-androstan-17β-yl acetate | 76251-33-7

• 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-oxo-4-aza-5-α-androstan-17β-yl acetate
• 英文别名: 17β-acetoxy-4-aza-5α-androstan-3-one；17-acetoxy-4-aza-5α-androstan-3-one；[(1S,3aS,3bR,5aR,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,8,9,9b,10,11-tetradecahydroindeno[5,4-f]quinolin-1-yl] acetate
• CAS: 76251-33-7
• 化学式: C₂₀H₃₁NO₃
• 分子量: 333.471
• InChiKey: QHJUNXVULYXDPT-MYTMCOJVSA-N

物化性质

• 沸点：
  471.8±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-4-aza-5-α-androstan-17β-yl acetate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以65%的产率得到4-Azadihydrotestosterone
  参考文献：
  名称：

  Crabb, Trevor A.; Ratcliffe, Norman M., Journal of Chemical Research, Miniprint, 1988, # 7, p. 1601 - 1618

  摘要：

  DOI：
• 作为产物：
  描述：

  3-((3S,3aS,5aS,6R,9aS,9bS)-3-acetoxy-3a,6-dimethyl-7-oxododecahydro-1H-cyclopenta[a]naphthalen-6-yl)propanoic acid 在 palladium on activated charcoal 氨 、 氢气 、 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 29.0h， 生成 3-oxo-4-aza-5-α-androstan-17β-yl acetate
  参考文献：
  名称：

  Crabb, Trevor A.; Ratcliffe, Norman M., Journal of Chemical Research, Miniprint, 1988, # 7, p. 1601 - 1618

  摘要：

  DOI：

文献信息

• N-chloroazasteroids: preparation of a novel class of thiophilic steroids
  作者：Thomas G. Back、Kurt Brunner

  DOI：10.1039/c39870001233

  日期：——

  The chlorination of various azasteroid lactams with N-chlorosuccinimide afforded novel N-chloroazasteroids which reacted with a model thiol to produce N-thioalkylated products and, in one case, a sulphenate ester.

  用N-氯代琥珀酰亚胺氯化多种氮杂甾体内酰胺，得到了新型N-氯氮杂甾体，其与模型硫醇反应生成N-硫代烷基化产物，在一种情况下还生成了亚磺酸酯。
• Oxidation of azasteroid lactams and alcohols with benzeneseleninic anhydride
  作者：Thomas G. Back

  DOI：10.1021/jo00320a040

  日期：1981.3
• 17-BETA-CYCLOPROPYL(AMINO/OXY) 4-AZA STEROIDS AS ACTIVE INHIBITORS OF TESTOSTERONE 5-ALPHA-REDUCTASE AND C17-20-LYASE
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP0880540B1

  公开（公告）日：2002-06-12
• Synthesis and biological activity of azasteroidal [3,2-c]- and [17,16-c]pyrazoles
  作者：R Gupta、D Pathak、DP Jindal

  DOI：10.1016/0223-5234(96)89140-9

  日期：1996.1

  Cholesterol, testosterone acetate and dehydroepiandrosterone acetate were used as starting materials for the preparation of azasteroidal [3,2-c]- and [17,16-c]pyrazole derivatives. In case of the 4-aza androstane series, a mixture of 5 alpha/5 beta epimers 8 was obtained, which were separated by chemical methods. The compounds 4, 5, 10, 12, 13, 15, 16 and 18-22 were screened for antiinflammatory activity using the carrageenan rat paw oedema model. Oxirane 22 was found to be around ten times more potent than hydrocortisone. Evaluation of compounds 14, 18 and 19 for their antineoplastic activity was also carried out at the National Cancer Institute, Bethesda, MD, USA, using standard procedures.
• N-Chloroazasteroids. A novel class of reactive steroid analogs. Preparation, reaction with thiols, and photochemical conversion to electrophilic N-acyl imines
  作者：Thomas G. Back、Kurt Brunner

  DOI：10.1021/jo00269a029

  日期：1989.4