17β-hydroxy-17α-methyl-3,5-seco-4-nor-5-oxo-androstan-3-oic acid | 2931-65-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 17β-hydroxy-17α-methyl-3,5-seco-4-nor-5-oxo-androstan-3-oic acid
• 英文别名: 17β-hydroxy-17α-methyl-5-oxo-3,5-seco-A-nor-androstan-3-oic acid；17β-Hydroxy-17α-methyl-5-oxo-3,5-seco-A-nor-androstan-3-saeure；17β-Hydroxy-17α-methyl-3.5-seco-4-nor-5-oxo-androstan-3-saeure；17β-Hydroxy-17α-methyl-5-oxo-3,5-seco-androstan-3-saeure；3-[(3S,3aS,5aS,6R,9aS,9bS)-3-hydroxy-3,3a,6-trimethyl-7-oxo-2,4,5,5a,8,9,9a,9b-octahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid
• CAS: 2931-65-9
• 化学式: C₁₉H₃₀O₄
• 分子量: 322.445
• InChiKey: UYMHYRPSWIDDSO-TULRTYAESA-N

物化性质

• 熔点：
  188-191 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  480.2±40.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-17α-methyl-3,5-seco-4-nor-5-oxo-androstan-3-oic acid 在 sodium hydroxide 、 tetrafluoroboric acid 、 potassium acetate 作用下， 以 乙醚 为溶剂， 反应 0.17h， 生成 17β-methoxy-17α-methyl-(10β-H)-des-A-androstan-5-one
  参考文献：
  名称：

  Rodewald, Wladyslaw J.; Jagodzinska, Barbara M., Polish Journal of Chemistry, 1980, vol. 54, # 4, p. 709 - 716

  摘要：

  DOI：
• 作为产物：
  描述：

  17-甲睾酮 在 溶剂黄146 作用下， 生成 17β-hydroxy-17α-methyl-3,5-seco-4-nor-5-oxo-androstan-3-oic acid
  参考文献：
  名称：

  Bolt, Recueil des Travaux Chimiques des Pays-Bas, 1951, vol. 70, p. 940,946

  摘要：

  DOI：

文献信息

• Development of a Commercial Process to Produce Oxandrolone
  作者：John E. Cabaj、David Kairys、Thomas R. Benson

  DOI：10.1021/op060231b

  日期：2007.5.1

  A manufacturing scale process for the preparation of the anabolic steroid Oxandrolone was developed. Key elements included the following: the bromination of methylandrostanolone with perbromide to give the 2-bromoketone in ca. 80% yield with minimal dehydration, subsequent elimination of the bromide with Li2CO3/LiBr to give the 2-enone in ca. 70% yield with minimal formation of methyltestosterone, and an ozonolysis procedure to give the penultimate intermediate in ca. 90% yield. The overall yield from methylandrostanolone to Oxandrolone using the described process was 45% as compared to the original Searle yield of 8%.