17-Hydroxymethylprogesteron | 65968-94-7

• 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: 17-Hydroxymethylprogesteron
• 英文别名: 17-Hydroxymethylprogesterone；(8R,9S,10R,13S,14S,17S)-17-acetyl-17-(hydroxymethyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 65968-94-7
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: NDRZPEKKCFHARJ-GUCLMQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,6β-Dibromo-17-hydroxymethyl-5α-pregnan-3,20-dion 在 溶剂黄146 、 锌 作用下， 生成 17-Hydroxymethylprogesteron
  参考文献：
  名称：

  Steroids and related products. XLVI. The regiospecific α-hydroxymethylation of saturated carbonyl compounds via preformed enolate ions. An improved synthesis of 17-hydroxymethyl 20-keto steroids

  摘要：

  As demonstrated for pregnenolone, saturated ketones are conveniently alpha-hydroxymethylated by their transformation into a lithium enolate and by the reaction of the latter with formaldehydr. The 17-hydroxymethylpregnenolone prepared by this method in very good yield was readily converted to 17-hydroxymethylprogesterone; either by selective acetylation in position 17(1) and subsequent Jones oxidation, followed by hydrolysis, or by conversion to the 4,5-dibromo 3-ketone - by bis(tri-n-butyltin)oxide-bromine oxidation or by dibromination and oxidation with N-bromoacetamde - and debromination with zinc and acetic acid.

  DOI：

  10.1016/s0039-128x(79)80021-5

文献信息

• Mukherjee,D.; Engel,C.R., Canadian Journal of Chemistry, 1978, vol. 56, p. 410 - 418
  作者：Mukherjee,D.、Engel,C.R.

  DOI：——

  日期：——
• Steroids and related products. XLVI. The regiospecific α-hydroxymethylation of saturated carbonyl compounds via preformed enolate ions. An improved synthesis of 17-hydroxymethyl 20-keto steroids
  作者：D. Mukherjee、Ch.R. Engel

  DOI：10.1016/s0039-128x(79)80021-5

  日期：1979.11

  As demonstrated for pregnenolone, saturated ketones are conveniently alpha-hydroxymethylated by their transformation into a lithium enolate and by the reaction of the latter with formaldehydr. The 17-hydroxymethylpregnenolone prepared by this method in very good yield was readily converted to 17-hydroxymethylprogesterone; either by selective acetylation in position 17(1) and subsequent Jones oxidation, followed by hydrolysis, or by conversion to the 4,5-dibromo 3-ketone - by bis(tri-n-butyltin)oxide-bromine oxidation or by dibromination and oxidation with N-bromoacetamde - and debromination with zinc and acetic acid.