(20S)-5β,14β-dimethyl-18,19-dinor-8α,9β,10α-cholest-13(17)ene | 28398-71-2

• 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: (20S)-5β,14β-dimethyl-18,19-dinor-8α,9β,10α-cholest-13(17)ene
• 英文别名: (5S,8S,9S,10S,14R)-5,14-dimethyl-17-[(2S)-6-methylheptan-2-yl]-2,3,4,6,7,8,9,10,11,12,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 28398-71-2
• 化学式: C₂₇H₄₆
• 分子量: 370.662
• InChiKey: FJCFWXCCRMONIJ-RYNAVYRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (20S)-5β,14β-dimethyl-18,19-dinor-8α,9β,10α-cholest-13(17)ene 生成 (20S)-13,17-secodiacholesta-13,17-dione
  参考文献：
  名称：

  Kirk; Shaw, Journal of the Chemical Society. Perkin transactions I, 1975, # 22, p. 2284 - 2294

  摘要：

  DOI：
• 作为产物：
  描述：

  5-胆甾烯 在 对甲苯磺酸 、 溶剂黄146 作用下， 生成 (20S)-5β,14β-dimethyl-18,19-dinor-8α,9β,10α-cholest-13(17)ene
  参考文献：
  名称：

  Kirk; Shaw, Journal of the Chemical Society. Perkin transactions I, 1975, # 22, p. 2284 - 2294

  摘要：

  DOI：

文献信息

• Reactions in dry media: reactions of cholesterol and cholestanes on silica bound ferric chloride
  作者：Daniel M. Tal、Ehud Keinan、Yehuda Mazur

  DOI：10.1016/0040-4020(81)85029-6

  日期：1981.1

  Reaction of cholesterol with silica bound FeCl3 resulted in a mixture of 3β-cholesteryl chloride and dicholesteryl ether.

  胆固醇与二氧化硅键合的FeCl 3的反应产生了3β-胆固醇酰氯和二胆固醇酯醚的混合物。
• Novel backbone rearrangement of steroids: formation of (20R and 20S) 1β,14β-dimethyl-18,19-dinor-5β,8α,9β,10α-cholest-13(17)-enes
  作者：Odette Sieskind、Jean-Pierre Kintzinger、Pierre Albrecht

  DOI：10.1039/c39890000133

  日期：——

  Two new 1-methyl rearranged sterenes were formed from cholestan-3β-ol and related compounds by a novel backbone reaction, catalysed by K10-montmorillonite; their structures were determined by 1H and 13C n.m.r. spectroscopy.

  在K10-蒙脱石的催化下，由胆甾醇3β-ol和相关化合物通过新颖的主链反应形成了两个新的1-甲基重排的甾烯。它们的结构由1 H和13 C nmr光谱确定。
• Peakman, Torren M.; Ellis, Karen; Maxwell, James R., Journal of the Chemical Society. Perkin transactions I, 1988, p. 1071 - 1076
  作者：Peakman, Torren M.、Ellis, Karen、Maxwell, James R.

  DOI：——

  日期：——
• Efficient synthesis of rearranged cholest-13(17)-enes catalysed by montmorillonite-clay
  作者：Odette Sieskind、Pierre Albrecht

  DOI：10.1016/s0040-4039(00)94800-7

  日期：——
• Studies of the synthesis of biomarkers. X. Synthesis of 13,17-secodiacholestanes
  作者：Li Tong-Shuang、Li Yu-Lin、Liang Xiao-Tian

  DOI：10.1016/0039-128x(92)90031-4

  日期：1992.2

  13,17-Secodiacholestanes (6) were synthesized from cholesterol (1) in six steps. The key intermediates, (20R)- and (20S)-diacholest-13(17)-enes (3a and 3b), underwent ozonization and reduction to provide (20R)- and (20S)-13,17-secodiacholesta-13,17-dione (5a and 5b), respectively. On Clemmensen reduction, the diones (5a and 5b) yielded the target molecule 6. The structure of an unknown biomarker was shown to be different from the proposed 6 by gas chromatographic/mass spectrometric comparison.