18-hydroxypregn-4-ene-3,20-dione(18<*>20) hemiketal-20-hydroperoxide | 1241-52-7

• 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: 18-hydroxypregn-4-ene-3,20-dione(18<*>20) hemiketal-20-hydroperoxide
• 英文别名: (1R,2S,5S,9R,12S,13R)-6-hydroperoxy-6,13-dimethyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-17-en-16-one
• CAS: 1241-52-7
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: FAUZKWKIPLKMIX-BSAOXSGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  18-hydroxypregn-4-ene-3,20-dione(18<*>20) hemiketal-20-hydroperoxide 在 吡啶 、 三甲胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.5h， 生成 17β-Hydroxy-18-acetoxyandrost-4-ene-3-one
  参考文献：
  名称：

  An improved synthesis of 18-norandrost-4-ene-3,17-dione

  摘要：

  We describe the synthesis of 13beta- and 13alpha-H-18-nor-androst-4-ene-3,17-dione (1a and 1b) from 18-hydroxyprogesterone (18 --> 20) hemiketal, via the 18-acetoxy-17beta-hydroxyandrost-4-en-3-one formed by a modified Baeyer-Villiger reaction. Saponification of 18-acetoxyandrost-4-ene-3,17-dione with sonication, then retroaldolization in the presence of a formaldehyde trap, methone, afforded the mixture of 1a and 1b with 80% yield in a ''one-pot'' procedure and at room temperature. This yield was greatly improved, compared with the already published procedure.

  DOI：

  10.1016/0039-128x(93)90051-n
• 作为产物：
  描述：

  18-hydroxypregn-4-ene-3,20-dione (18<*>20)hemiketal 在 双氧水 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以2.1 g的产率得到18-hydroxypregn-4-ene-3,20-dione(18<*>20) hemiketal-20-hydroperoxide
  参考文献：
  名称：

  An improved synthesis of 18-norandrost-4-ene-3,17-dione

  摘要：

  We describe the synthesis of 13beta- and 13alpha-H-18-nor-androst-4-ene-3,17-dione (1a and 1b) from 18-hydroxyprogesterone (18 --> 20) hemiketal, via the 18-acetoxy-17beta-hydroxyandrost-4-en-3-one formed by a modified Baeyer-Villiger reaction. Saponification of 18-acetoxyandrost-4-ene-3,17-dione with sonication, then retroaldolization in the presence of a formaldehyde trap, methone, afforded the mixture of 1a and 1b with 80% yield in a ''one-pot'' procedure and at room temperature. This yield was greatly improved, compared with the already published procedure.

  DOI：

  10.1016/0039-128x(93)90051-n

文献信息

• An improved synthesis of 18-norandrost-4-ene-3,17-dione
  作者：Elisabeth Davioud、Philippe Schambel、Antoinette Viger、Andrée Marquet

  DOI：10.1016/0039-128x(93)90051-n

  日期：1993.3

  We describe the synthesis of 13beta- and 13alpha-H-18-nor-androst-4-ene-3,17-dione (1a and 1b) from 18-hydroxyprogesterone (18 --> 20) hemiketal, via the 18-acetoxy-17beta-hydroxyandrost-4-en-3-one formed by a modified Baeyer-Villiger reaction. Saponification of 18-acetoxyandrost-4-ene-3,17-dione with sonication, then retroaldolization in the presence of a formaldehyde trap, methone, afforded the mixture of 1a and 1b with 80% yield in a ''one-pot'' procedure and at room temperature. This yield was greatly improved, compared with the already published procedure.