11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone | 1398078-09-5

• 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: 11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
• CAS: 1398078-09-5
• 化学式: C₂₃H₃₁NO₆
• 分子量: 417.502
• InChiKey: YUSAASPFAZQJGG-PXMJCRCBSA-N

物化性质

• 沸点：
  646.5±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  106.74
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone 在 dipotassium hydrogenphosphate 、 甲酸 、 硝基甲烷 、 2,2,2-三氯乙酰胺 、 双氧水 、 potassium formate 、 十八烷基二甲基苄基氯化铵 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.5h， 生成 依普利酮
  参考文献：
  名称：

  A diastereoselective synthesis of 7α-nitromethyl steroid derivative and its use for an efficient synthesis of eplerenone

  摘要：

  A novel and efficient method of stereoselectively introducing alpha-nitromethyl group to C-7 position of 11 alpha-hydroxyl canrenone 4 was described. In addition, this method was successfully applied in a total synthesis of Eplerenone 8. The route was characteristic of simple operation, moderate reaction conditions with 5 steps and 55% total yield, at the same time, without any expensive or toxic reagent in use. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.04.017
• 作为产物：
  描述：

  11-alpha-羟基坎利酮 、 硝基甲烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以25%的产率得到11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
  参考文献：
  名称：

  A diastereoselective synthesis of 7α-nitromethyl steroid derivative and its use for an efficient synthesis of eplerenone

  摘要：

  A novel and efficient method of stereoselectively introducing alpha-nitromethyl group to C-7 position of 11 alpha-hydroxyl canrenone 4 was described. In addition, this method was successfully applied in a total synthesis of Eplerenone 8. The route was characteristic of simple operation, moderate reaction conditions with 5 steps and 55% total yield, at the same time, without any expensive or toxic reagent in use. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.04.017