17,20:20,21-bismethylenedioxy-11β-hydroxy-5β-pregnan-3-one | 102900-58-3

• 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: 17,20:20,21-bismethylenedioxy-11β-hydroxy-5β-pregnan-3-one
• CAS: 102900-58-3
• 化学式: C₂₃H₃₄O₆
• 分子量: 406.519
• InChiKey: WMOCWGJGTDLMSA-PXPIOOTJSA-N

物化性质

• 熔点：
  239-240 °C(Solv: methanol (67-56-1))
• 沸点：
  536.7±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  29.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  17,20:20,21-bismethylenedioxy-11β-hydroxy-5β-pregnan-3-one 在 吡啶 、 sodium hydroxide 、 sodium borodeuteride 、 氢氟酸 、 sodium acetate 、 三甲基铵三氧化硫共聚物 、 pyridinium chlorochromate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 CH₃OD 、 D₂D 、 重水 为溶剂， 反应 46.0h， 生成 [2,2,3β,4,4-d5]-3α,17α-dihydroxy-21-sulfooxy-5β-pregnane-11,20-dione sodium
  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 10% Pd(OH)₂ on C 、 氢气 作用下， 以 吡啶 为溶剂， 以67%的产率得到17,20:20,21-bismethylenedioxy-11β-hydroxy-5β-pregnan-3-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