5β-cholan-3β-ol | 42921-44-8

• 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: 5β-cholan-3β-ol
• 英文别名: Cholan-3-ol, (3beta,5beta)-；(3S,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-pentan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 42921-44-8
• 化学式: C₂₄H₄₂O
• 分子量: 346.597
• InChiKey: ODFHHECDCZZICL-QFGBFBPLSA-N

物化性质

• 熔点：
  134-135 °C
• 沸点：
  428.4±13.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5β-cholan-3β-ol 在 collision-induced decomposition 作用下， 生成
  参考文献：
  名称：

  Translational energy release and stereochemistry of steroids. IX-The mechanism of the elimination of water from metastable ions in epimeric 3-hydroxy steroids of the 5β-series

  摘要：

  AbstractThe mechanism of water elimination from metastable molecular and [M − CH3˙]+ ions, as well as from ions deprived of ring D, in epimeric 3‐hydroxy steroids of the 5β‐series has been elucidated by deuterium labelling, by the measurements of the translational energy released during loss of water, and by collision‐induced decomposition mass‐analysed ion kinetic energy spectrometry. It was found that the dehydration of the metastable molecular ion in 3α‐hydroxy steroids of the 5β‐series occurs mostly regiospecifically as an elimination of the 3α‐hydroxyl together with the 9α‐hydrogen atom. The ring A in the molecular ion has to flip to the boat conformation to make this reaction possible. In the metastable molecular ion of 3β‐hydroxy steroids of the 5β‐series a different dehydration mechanism operates, with very little participation of the 9α‐hydrogen atom. The mechanisms of water loss from metastable [M − CH3˙]+ ions and from ions deprived of ring D differ from that of the molecular ion.

  DOI：

  10.1002/oms.1210230606
• 作为产物：
  描述：

  3α,12α,24-trihydroxy-5β-cholane 反应 2.0h， 生成 5β-cholan-3β-ol
  参考文献：
  名称：

  Klein,H.; Djerassi,C., Chemische Berichte, 1973, vol. 106, p. 1897 - 1904

  摘要：

  DOI：

文献信息

• A review of porcine tonsils in immunity and disease
  作者：Dennis C. Horter、Kyoung-Jin Yoon、Jeffrey J. Zimmerman

  DOI：10.1079/ahrr200358

  日期：2003.12
• Klein,H.; Djerassi,C., Chemische Berichte, 1973, vol. 106, p. 1897 - 1904
  作者：Klein,H.、Djerassi,C.

  DOI：——

  日期：——
• Translational energy release and stereochemistry of steroids. IX-The mechanism of the elimination of water from metastable ions in epimeric 3-hydroxy steroids of the 5β-series
  作者：Z. V. I. Zaretskii、J. M. Curtis、A. G. Brenton、J. H. Beynon、Carl Djerassi

  DOI：10.1002/oms.1210230606

  日期：1988.6

  AbstractThe mechanism of water elimination from metastable molecular and [M − CH3˙]+ ions, as well as from ions deprived of ring D, in epimeric 3‐hydroxy steroids of the 5β‐series has been elucidated by deuterium labelling, by the measurements of the translational energy released during loss of water, and by collision‐induced decomposition mass‐analysed ion kinetic energy spectrometry. It was found that the dehydration of the metastable molecular ion in 3α‐hydroxy steroids of the 5β‐series occurs mostly regiospecifically as an elimination of the 3α‐hydroxyl together with the 9α‐hydrogen atom. The ring A in the molecular ion has to flip to the boat conformation to make this reaction possible. In the metastable molecular ion of 3β‐hydroxy steroids of the 5β‐series a different dehydration mechanism operates, with very little participation of the 9α‐hydrogen atom. The mechanisms of water loss from metastable [M − CH3˙]+ ions and from ions deprived of ring D differ from that of the molecular ion.