17β-hydroxy-7α-methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone | 1263102-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 17β-hydroxy-7α-methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
• 英文别名: (1R,6R,10S,11R,14S,15R,16R)-6,10-dimethylspiro[18-oxapentacyclo[14.2.1.01,6.07,15.010,14]nonadec-7-ene-11,5'-oxolane]-2',3-dione
• CAS: 1263102-65-3
• 化学式: C₂₃H₃₀O₄
• 分子量: 370.489
• InChiKey: FHZNBCCNYGFNNM-DNECWOSGSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  557.9±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-7α-methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone 在 甲基(三氟甲基)-1,3-二环氧丙烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到17β-hydroxy-7α-(1'-hydroxy)methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
  参考文献：
  名称：

  Stereoselective construction of a steroid 5α,7α-oxymethylene derivative and its use in the synthesis of eplerenone

  摘要：

  A new and practical method for a stereoselective construction of a steroid 5 alpha,7 alpha-oxymethylene derivative has been developed and successfully applied to the stereoselective synthesis of eplerenone (8). Starting with available 11 alpha-hydroxyl canrenone (1), eplerenone (8) was synthesised in seven steps with a 48% overall yield. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.08.009
• 作为产物：
  描述：

  11-alpha-羟基坎利酮 在 potassium fluoride 、 copper(I) iodide-lithium chloride 、 三氟化硼乙醚 、 双氧水 、 potassium acetate 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲酸 、 二氯甲烷 、 水 、 乙酸酐 为溶剂， 反应 20.0h， 生成 17β-hydroxy-7α-methylene-5α-oxo-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
  参考文献：
  名称：

  Stereoselective construction of a steroid 5α,7α-oxymethylene derivative and its use in the synthesis of eplerenone

  摘要：

  A new and practical method for a stereoselective construction of a steroid 5 alpha,7 alpha-oxymethylene derivative has been developed and successfully applied to the stereoselective synthesis of eplerenone (8). Starting with available 11 alpha-hydroxyl canrenone (1), eplerenone (8) was synthesised in seven steps with a 48% overall yield. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.08.009

文献信息

• Stereoselective construction of a steroid 5α,7α-oxymethylene derivative and its use in the synthesis of eplerenone
  作者：Bin Zhang、Hongli Chen、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.steroids.2010.08.009

  日期：2011.1

  A new and practical method for a stereoselective construction of a steroid 5 alpha,7 alpha-oxymethylene derivative has been developed and successfully applied to the stereoselective synthesis of eplerenone (8). Starting with available 11 alpha-hydroxyl canrenone (1), eplerenone (8) was synthesised in seven steps with a 48% overall yield. (C) 2010 Elsevier Inc. All rights reserved.