3β-acetoxy-8α,9α-epoxy-5α-cholestan-7,11-dione | 157396-43-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-acetoxy-8α,9α-epoxy-5α-cholestan-7,11-dione
• 英文别名: 3β-acetoxy-8,9-epoxy-5α,8α-cholestane-7,11-dione；3β-Acetoxy-8,9-epoxy-5α,8α-cholestan-7,11-dion
• CAS: 157396-43-5
• 化学式: C₂₉H₄₄O₅
• 分子量: 472.665
• InChiKey: RYVZPTOICBTKSV-KNUMMSEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 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：
  0.9
• 拓扑面积：
  72.97
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-8α,9α-epoxy-5α-cholestan-7,11-dione 在 四氢呋喃 、 盐酸 、 甲醇 、 氢氧化钾 、 lithium aluminium tetrahydride 、 镍 、 溶剂黄146 、 锌 作用下， 生成 5α-cholest-9(11)-en-3β-ol
  参考文献：
  名称：

  Synthesis of Δ⁹⁽¹¹⁾- and Δ²⁰⁽²²⁾-Cholestenol

  摘要：

  DOI：

  10.1021/ja01117a063
• 作为产物：
  描述：

  3β-acetoxy-8α,9α-epoxy-7α-hydroxy-5α-cholestan-11-one 在 chromium trioxide pyridine 作用下， 生成 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

文献信息

• Über Steroide und Sexualhormone. 177. Mitteilung. Ein neuer Weg zur Synthese von 11-Keto-Steroiden II. Versuche in der Androstan- und der Cholestan-Reihe
  作者：H. Heusser、K. Heusler、K. Eichenberger、C. G. Honegger、O. Jeger

  DOI：10.1002/hlca.19520350138

  日期：1952.2.1

  „Ein neuer Weg zur Synthese von 11-Keto-Steroiden” (l. c.) geben wir in der vorliegenden Mitteilung weitere Resultate bekannt, die in der Androstan- und der Cholestan-Reihe erzielt wurden. Die Endprodukte dieser Versuche sind das 3,11,17-Triketo-androstan (IX) und das 3β-Acetoxy-11-keto-cholestan (XVII).

  除了我们最近发表的著作“合成11-酮-类固醇的新途径”（lc）之外，在本新闻稿中，我们还宣布了雄甾烷和胆甾烷系列所取得的进一步结果。这些实验的最终产物是3,11,17-三酮-雄烷（IX）和3β-乙酰氧基-11-酮-胆甾烷（XVII）。