17,17-dimethoxyandrost-5-ene-3β,7α,16α-triol | 880517-93-1

• 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: 17,17-dimethoxyandrost-5-ene-3β,7α,16α-triol
• CAS: 880517-93-1
• 化学式: C₂₁H₃₄O₅
• 分子量: 366.498
• InChiKey: QCAOFUUWWBCTLT-GHDZTLAJSA-N

物化性质

• 熔点：
  225-228 °C (decomp)(Solv: ethyl ether (60-29-7))
• 沸点：
  506.0±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  17,17-dimethoxyandrost-5-ene-3β,7α,16α-triol 在 对甲苯磺酸一水合物 作用下， 以 吡啶 、 水 、 丙酮 为溶剂， 反应 2.25h， 生成
  参考文献：
  名称：

  Derivatives of 16α-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: Synthesis and gas chromatography/mass spectrometry analysis

  摘要：

  Derivatives of 16 alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3 beta, 16 alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by L-Selectride (R) or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7 alpha-hydroxy and 7 beta-hydroxy derivatives of 16 alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by H-1 and C-13 NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.04.002
• 作为产物：
  描述：

  17,17-dimethoxy-7α-hydroxyandrost-5-ene-3β,16α-diyl diacetate 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以86%的产率得到17,17-dimethoxyandrost-5-ene-3β,7α,16α-triol
  参考文献：
  名称：

  Derivatives of 16α-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: Synthesis and gas chromatography/mass spectrometry analysis

  摘要：

  Derivatives of 16 alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3 beta, 16 alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by L-Selectride (R) or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7 alpha-hydroxy and 7 beta-hydroxy derivatives of 16 alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by H-1 and C-13 NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2005.04.002