3β-acetoxy-17aβ-hydroxy-17aα-methyl-D-homo-5-androsten-17-one | 2302-10-5

• 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: 3β-acetoxy-17aβ-hydroxy-17aα-methyl-D-homo-5-androsten-17-one
• 英文别名: 17aβ-hydroxy-3β-acetoxy-17aα-methyl-D-homo-androsten-(5)-one-(17)；17aβ-Hydroxy-3β-acetoxy-17aα-methyl-D-homo-androsten-(5)-on-(17)；3β-Acetoxy-17-oxo-17aβ-hydroxy-17aα-methyl-D-homo-Δ⁵-androsten
• CAS: 2302-10-5
• 化学式: C₂₃H₃₄O₄
• 分子量: 374.521
• InChiKey: WHXXRFQGHUUAGH-ZGIWMXSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  17Alpha-羟基妊娠烯醇酮 在 吡啶 、 sodium hydride 、 6-甲巯基嘌呤 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 3β-acetoxy-17aβ-hydroxy-17aα-methyl-D-homo-5-androsten-17-one
  参考文献：
  名称：

  Nucleosteroids: Reaction of activated purine bases with steroidal reactive centers

  摘要：

  The reaction of 16 alpha,17 alpha-epoxy-3 beta-hydroxy-5-pregnen-20-one with 6-methyl thiopurine activated with sodium hydride leads to the coupling of the purine base with the carbonyl group at C-20 to give a steroidal nucleoside analog, which is termed ''nucleosteroid.'' In the presence of an excess of purine, a parallel reaction occurs in which the oxirane ring is opened, presumably by nucleophilic attack of an intermediate C-20 oxyanion, and yields as the main product of reaction an oligomeric mixture of nucleosteroid units linked together by ether linkages. Analogous reactions conducted with 3 beta-hydroxy-5-pregnen-20-one and with 3 beta,17 alpha-dihydroxy-5-pregnen-20-one gave minor amounts or only traces of the corresponding coupling adduct, and oligomerization did nor occur. This behavior is interpreted in terms of the conformational differences showed by the different steroids to the attack by the purine. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00199-7

文献信息

• Molecular Rearrangements of 17-Hydroxy-pregnane Compounds¹
  作者：Homer E. Stavely

  DOI：10.1021/ja01856a069

  日期：1941.11
• Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 58. Mitteilung. Über Umlagerungen von 17-Oxy-20-keto-steroiden in Polyhydrochrysen-Derivate. Acetylierungen in Gegenwart von Borfluorid
  作者：C. W. Shoppee、D. A. Prins

  DOI：10.1002/hlca.19430260127

  日期：1943.2.1
• Die Umlagerung von 17-Oxy-20-keto-steroiden III
  作者：C. W. Shoppee、D. A. Prins

  DOI：10.1002/hlca.19430260331

  日期：1943.5.3