3β-acetoxy-14α,15α-epoxy-5α-cholest-8-en-7-one | 71076-39-6

• 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: 3β-acetoxy-14α,15α-epoxy-5α-cholest-8-en-7-one
• 英文别名: [(2S,4S,6R,7R,11S,14S,16R)-7,11-dimethyl-6-[(2R)-6-methylheptan-2-yl]-18-oxo-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadec-1(10)-en-14-yl] acetate
• CAS: 71076-39-6
• 化学式: C₂₉H₄₄O₄
• 分子量: 456.666
• InChiKey: FMJGDKYYSGDDGP-DXKHZCIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-14α,15α-epoxy-5α-cholest-8-en-7-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.08h， 生成 3β-acetoxy-9α-methoxy-5α-cholest-8(14)-en-7,15-dione
  参考文献：
  名称：

  Elucidation of the opening of the epoxidic ring of the 3β-acetoxy-14α,15α-epoxy-5α-cholest-8-en-7-one by methanol, using NMR techniques assisted by a conformational study through theoretical calculations

  摘要：

  This paper demonstrates that the crystallization of 3 beta-acetoxy-14 alpha,15 alpha-epoxy-5 alpha-cholest-8en-7-one from methanol affords the 3 beta-acetoxy-9 alpha.-methoxy-15 alpha-hydroxycholest-8(14)-en7-one. The structure of this steroid, which shows an apparently anomalous UV absorption maximum, is determined by high field NMR experiments, supporting the coupling constant values assignments and the NOE contacts by a conformational study through theoretical calculations at the B3LYP/6-31G* level. The computational study also justifies the observed UV absorption of the steroid, thus demonstrating the usefulness of computer chemistry in providing support for the identification of unknown compounds. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.07.004
• 作为产物：
  描述：

  3β-acetoxy-5α-cholesta-8,14-dien-7-one 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 42.0h， 生成 3β-acetoxy-14α,15α-epoxy-5α-cholest-8-en-7-one
  参考文献：
  名称：

  Elucidation of the opening of the epoxidic ring of the 3β-acetoxy-14α,15α-epoxy-5α-cholest-8-en-7-one by methanol, using NMR techniques assisted by a conformational study through theoretical calculations

  摘要：

  This paper demonstrates that the crystallization of 3 beta-acetoxy-14 alpha,15 alpha-epoxy-5 alpha-cholest-8en-7-one from methanol affords the 3 beta-acetoxy-9 alpha.-methoxy-15 alpha-hydroxycholest-8(14)-en7-one. The structure of this steroid, which shows an apparently anomalous UV absorption maximum, is determined by high field NMR experiments, supporting the coupling constant values assignments and the NOE contacts by a conformational study through theoretical calculations at the B3LYP/6-31G* level. The computational study also justifies the observed UV absorption of the steroid, thus demonstrating the usefulness of computer chemistry in providing support for the identification of unknown compounds. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.07.004