2α,3α-methano-3β-(2-chloroethoxy)-5α-cholestane | 256455-52-4

• 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: 2α,3α-methano-3β-(2-chloroethoxy)-5α-cholestane
• CAS: 256455-52-4
• 化学式: C₃₀H₅₁ClO
• 分子量: 463.187
• InChiKey: MWWLWEDHOWEZRN-RXNYWDMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2α,3α-methano-3β-(2-chloroethoxy)-5α-cholestane 在 正丁基锂 作用下， 以 乙二醇二甲醚 、 正己烷 为溶剂， 反应 0.83h， 以65%的产率得到2α,3α-cyclopropano-5α-cholestan-3β-ol
  参考文献：
  名称：

  A C₆-Flavin Adduct Is the Major Product of Irreversible Inactivation of Cholesterol Oxidase by 2α,3α-Cyclopropano-5α-cholestan-3β-ol

  摘要：

  We have synthesized 2 alpha,3 alpha-cyclopropano-5 alpha-cholestan-3 beta-ol and tested it as a substrate and inhibitor of cholesterol oxidase. The cyclopropylsterol irreversibly inhibits cholesterol oxidase with a k(inact) = 0.010 min(-1) and K-i = 36 mu M. Efficient inactivation requires the general base His(447). TWO FAD-steroid adducts were isolated by reversed-phase HPLC. The UV/vis, fluorescence and mass spectra of the adducts suggest that the FAD cofactor acts as an electrophile in a cyclopropoxide ring-opening reaction to form a C-6-alkylated flavin (68%) and either an N-5 flavin adduct or a cyclic N-5-C-4a flavin adduct (32%). Cyclopropoxide ring-opening to form a C-6-FAD adduct represents a new approach to flavoenzyme inhibition.

  DOI：

  10.1021/ja992053q
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 52.0h， 生成 2α,3α-methano-3β-(2-chloroethoxy)-5α-cholestane
  参考文献：
  名称：

  A C₆-Flavin Adduct Is the Major Product of Irreversible Inactivation of Cholesterol Oxidase by 2α,3α-Cyclopropano-5α-cholestan-3β-ol

  摘要：

  We have synthesized 2 alpha,3 alpha-cyclopropano-5 alpha-cholestan-3 beta-ol and tested it as a substrate and inhibitor of cholesterol oxidase. The cyclopropylsterol irreversibly inhibits cholesterol oxidase with a k(inact) = 0.010 min(-1) and K-i = 36 mu M. Efficient inactivation requires the general base His(447). TWO FAD-steroid adducts were isolated by reversed-phase HPLC. The UV/vis, fluorescence and mass spectra of the adducts suggest that the FAD cofactor acts as an electrophile in a cyclopropoxide ring-opening reaction to form a C-6-alkylated flavin (68%) and either an N-5 flavin adduct or a cyclic N-5-C-4a flavin adduct (32%). Cyclopropoxide ring-opening to form a C-6-FAD adduct represents a new approach to flavoenzyme inhibition.

  DOI：

  10.1021/ja992053q