4α,5-cyclopropano-5α-cholestan-3α-ol | 13903-63-4

• 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: 4α,5-cyclopropano-5α-cholestan-3α-ol
• CAS: 13903-63-4
• 化学式: C₂₈H₄₈O
• 分子量: 400.689
• InChiKey: NHCFIELJCQCTTN-QYAGBQGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4α,5-cyclopropano-5α-cholestan-3α-ol 在 chromium trioxide-pyridine complex 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到4α,5α-methano-5β-cholestan-3-one
  参考文献：
  名称：

  4,5-Cyclopropanocholestan-3β-ol Substrates for Cholesterol Oxidase and Their ¹H NMR Assignments

  摘要：

  We have assayed 4,5-cyclopropanocholestan-3-ols and 4,5-cyclopropanocholestan-3-ones and tested them as substrates and inhibitors of cholesterol oxidase. The 4,5-cyclopropanocholestan-3 beta-ols (alpha and beta) are substrates of cholesterol oxidase that are converted to their respective ketones 1000-fold more slowly than cholesterol. The induced ring-current effects of a cyclopropane ring are clearly illustrated in the H-1 NMR spectra of these sterols. These shielding effects are dramatic because of the rigidity of the steroid backbone. Assignments of the H-1 resonances of the A, B, and cyclopropyl rings of the sterols have been made using DQF-COSY and NOESY experiments. We have assigned the upheld multiplet at approximately 0.5 ppm to H-6 alpha in both isomers. H-6 alpha is Shielded by the cyclopropyl sigma bond. H-6 beta is deshielded by the cyclopropane ring and appears at approximately 2.0 ppm in both isomers.

  DOI：

  10.1021/jo9706537
• 作为产物：
  描述：

  4α,5α-methano-5β-cholestan-3β-ol 在 jones' reagent 、 lithium tri(t-butoxy)aluminum hydride 作用下， 以 乙二醇二甲醚 、 丙酮 为溶剂， 反应 2.25h， 生成 4α,5-cyclopropano-5α-cholestan-3α-ol
  参考文献：
  名称：

  Joska, Jiri; Fajkos, Jan, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 6, p. 1850 - 1859

  摘要：

  DOI：