16α,17α-epoxy-5α-pregnane-3β,21-diol-20-one-20-ethoxycarbonylhydrazone | 135508-20-2

• 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: 16α,17α-epoxy-5α-pregnane-3β,21-diol-20-one-20-ethoxycarbonylhydrazone
• 英文别名: 16α,17α-epoxy-5α-pregnan-3β,21-diol-20-one 20-carbethoxyhydrazone
• CAS: 135508-20-2
• 化学式: C₂₄H₃₈N₂O₅
• 分子量: 434.576
• InChiKey: LNHXDYDPMFRCBR-FYYJOIONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  103.68
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  16α,17α-epoxy-5α-pregnane-3β,21-diol-20-one-20-ethoxycarbonylhydrazone 在 盐酸 、 高氯酸 、 对苯二酚 、 硫代乙酸 作用下， 反应 58.0h， 生成 5α-pregnan-3β,16α,21-triol-17α-thiol-20-one 16α,17α-acetonide
  参考文献：
  名称：

  Transformed steroids. 189. Synthesis and transformations of 21-hydroxy-5?-H-pregnane 2?,2?-dimethyl-[16?,17?-d]-thioxalanes

  摘要：

  In a continuation of the research on use of 20-keto-16alpha,17alpha-epoxysteroid 20-hydrazones for synthesis of 17-thio analogs of 20-ketosteroid 16alpha,17alpha-acetonides [2, 3], we synthesized 5alpha-H-pregnane-3beta,16alpha,21-trihydroxy-17alpha-thiol-20-one 16,17-acetonide and found methods for its microbiological dehydrogenation and hydroxylation into DELTA4-3-keto- and 9alpha-hydroxy-DELTA4-3-keto derivatives.

  DOI：

  10.1007/bf00864542
• 作为产物：
  描述：

  (3β,5α,16α)-16,17-epoxy-3-hydroxypregnan-20-one 在 氢氧化钾 、 碘苯二乙酸 、 吡啶盐酸盐 、 对甲苯磺酸 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 21.0h， 生成 16α,17α-epoxy-5α-pregnane-3β,21-diol-20-one-20-ethoxycarbonylhydrazone
  参考文献：
  名称：

  Synthesis and transformations of the 20-substituted derivatives of 16?,17?-epoxy-5?-pregnane-3?,21-diol-20-ones

  摘要：

  A new and more effective sequence of reactions is proposed for the production of 16-alpha,17-alpha-isopropylidenedioxy-5-alpha-pregnane-3-beta,21-diol-20-one. It uses methods previously unused for 5-alpha-H-steroids and involves 21-hydroxylation of 16-alpha,17-alpha-epoxy-5-alpha-pregnan-3-beta-ol-20-one with diacetoxyiodobenzene and cis-opening of the obtained 21-hydroxy-16-alpha,17-alpha-epoxy-5-alpha-pregnane-3-beta,21-diol-20-one by acetic acid in the presence of epoxycarbonylhydrazine, followed by condensation of the obtained product with acetone.

  DOI：

  10.1007/bf00961375