3α-acetoxy-17,20:20,21-bismethylenedioxy-5β-pregnan-11-one | 1338579-70-6

• 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: 3α-acetoxy-17,20:20,21-bismethylenedioxy-5β-pregnan-11-one
• CAS: 1338579-70-6
• 化学式: C₂₅H₃₆O₇
• 分子量: 448.557
• InChiKey: AWQLYZAQQAGPBV-ROAFLRAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  32.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3α-acetoxy-17,20:20,21-bismethylenedioxy-5β-pregnan-11-one 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以84%的产率得到17,20:20,21-bismethylenedioxy-3α-hydroxy-5β-pregnan-11-one
  参考文献：
  名称：

  Synthesis of 3- and 21-monosulfates of [2,2,3β,4,4-2H5]-tetrahydrocorticosteroids in the 5β-series as internal standards for mass spectrometry

  摘要：

  The 3- and 21-monosulfates of pentadeuterated 5 beta-tetrahydrocorticosteroides were synthesized, starting from cortisol and 11-deoxycotisol. The principal reactions used were (1) perdeuteration of the methylene groups adjacent to the 3-oxo group of 17,20:20,21-bismethylendioxy-5 beta-3-ketosteroids with NaOD in CH3OD followed by stereoselective reduction with NaBD4, (2) sulfation of hydroxy groups with sulfur trioxide-trimethylamine complex, and (3) removal of the 17,20:20,21-bismethylendioxy group with hydrogen fluoride. The labeled compounds can be used as internal standards in liquid chromatography/mass spectrometry assays for clinical and biochemical studies. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.014
• 作为产物：
  描述：

  11β-hydroxy-17α,20:20,21-bis(methylenedioxy)pregn-4-en-3-one 在 吡啶 、 sodium tetrahydroborate 、 Jones reagent 、 10% Pd(OH)₂ on C 、 氢气 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 丙酮 为溶剂， 反应 11.0h， 生成 3α-acetoxy-17,20:20,21-bismethylenedioxy-5β-pregnan-11-one
  参考文献：
  名称：

  Synthesis of 3- and 21-monosulfates of [2,2,3β,4,4-2H5]-tetrahydrocorticosteroids in the 5β-series as internal standards for mass spectrometry

  摘要：

  The 3- and 21-monosulfates of pentadeuterated 5 beta-tetrahydrocorticosteroides were synthesized, starting from cortisol and 11-deoxycotisol. The principal reactions used were (1) perdeuteration of the methylene groups adjacent to the 3-oxo group of 17,20:20,21-bismethylendioxy-5 beta-3-ketosteroids with NaOD in CH3OD followed by stereoselective reduction with NaBD4, (2) sulfation of hydroxy groups with sulfur trioxide-trimethylamine complex, and (3) removal of the 17,20:20,21-bismethylendioxy group with hydrogen fluoride. The labeled compounds can be used as internal standards in liquid chromatography/mass spectrometry assays for clinical and biochemical studies. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.014