8α,9α-epoxy-11α-hydroxy-7-oxo-5α-cholestan-3β-yl acetate | 115760-47-9

• 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: 8α,9α-epoxy-11α-hydroxy-7-oxo-5α-cholestan-3β-yl acetate
• 英文别名: 3β-acetoxy-8α,9α-epoxy-11α-hydroxy-5α-cholestan-7-one；3β-acetoxy-8,9-epoxy-11α-hydroxy-5α,8α-cholestan-7-one；3β-Acetoxy-8,9-epoxy-11α-hydroxy-5α,8α-cholestan-7-on
• CAS: 115760-47-9
• 化学式: C₂₉H₄₆O₅
• 分子量: 474.681
• InChiKey: PMDDMXIQMUPROG-TXVNXSQQSA-N

物化性质

• 沸点：
  574.0±50.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  76.13
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  8α,9α-epoxy-11α-hydroxy-7-oxo-5α-cholestan-3β-yl acetate 在 chromium trioxide pyridine 作用下， 反应 16.0h， 以1.1 mg的产率得到3β-acetoxy-8α,9α-epoxy-5α-cholestan-7,11-dione
  参考文献：
  名称：

  Studies towards the synthesis of polyoxygenated steroids. Reaction of 7,9(11)-diene steroids with RuO4.

  摘要：

  In order to find an entry to C-ring oxygenated steroids, the reaction of ruthenium tetroxide with some Delta(7,9(11))-sterols gas been explored. The reaction has been performed both at -70 degrees C and room temperature using an equimolecular amount of the oxidant and acetone-water as solvent system in the absence of a cooxidant. The change in the temperature conditions moderately affects the yields of the reaction products. When 3 beta,6 alpha- and 3 beta,6 beta-diacetoxy-Delta(7,9(11))-sterols were used the diene system was predominantly attacked at the 9(11)-double bond from the alpha-face of the molecule giving Delta(7)-9 alpha-hydroxy-11-keto- and Delta(7)-9 alpha,11 alpha-dihydroxy-sterols. RuO4 oxidation of cholesta-7,9(11)-dien-3 beta-yl acetate, yielded, in addition to the above oxidation products, minor amounts of three related C-7,C-11 oxigenated 8 alpha,9 alpha-epoxysterols, arising from the oxidation of both double bonds of the diene system. These results, that in part parallel those we recently found on RuO4 oxidation of trisubstituted [Delta(4), Delta(5) and Delta(7)] steroidal alkenes, shed further light on the reactivity of this oxidizing agent which, neverthless, seems far from being completely understood. In addition, our procedure furnishes a reliable route to Delta(7)-9 alpha,11 beta-dihydroxysterols via LiAlH4 reduction of the 11-keto group.

  DOI：

  10.1016/s0040-4020(01)85020-1
• 作为产物：
  描述：

  11α-hydroxy-7-oxo-5α-cholest-8-en-3β-yl acetate 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 8α,9α-epoxy-11α-hydroxy-7-oxo-5α-cholestan-3β-yl acetate
  参考文献：
  名称：

  Lasalvia, Maria; Musumeci, Domenica; Piccialli, Vincenzo, Journal of Chemical Research, Miniprint, 1998, # 11, p. 2988 - 2995

  摘要：

  DOI：

文献信息

• Synthesis of Δ⁹⁽¹¹⁾- and Δ²⁰⁽²²⁾-Cholestenol
  作者：Louis F. Fieser、Wei-Yuan Huang

  DOI：10.1021/ja01117a063

  日期：1953.11