3,3-ethylenedioxy-5β-cholestane | 25328-53-4

• 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: 3,3-ethylenedioxy-5β-cholestane
• 英文别名: 3-cholestanone ethylene ketal；3,3-ethanediyldioxy-5β-cholestane；3,3-Aethandiyldioxy-5β-cholestan；5beta-Cholestan-3-one ethylene acetal；(5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]spiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]
• CAS: 25328-53-4
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: NCAQEOULCQQMGY-SMIFZSHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-ethylenedioxy-5β-cholestane 在 Montmorillonite K 10 、 水 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以97%的产率得到(5beta)-胆甾烷-3-酮
  参考文献：
  名称：

  Montmorillonite Clay Catalysis. Part 3¹: A New Ready and High Yield Procedure for the Cleavage of Acetals Catalysed by Montmorillonite K 10

  摘要：

  An easy cleavage of acetals has been carried out in excellent yield under catalysis of montmorillonite K 10 in refluxing wet acetone.

  DOI：

  10.1080/00397919708003385
• 作为产物：
  描述：

  2-乙基-2-甲基-1,3-二氧杂烷 、 (5beta)-胆甾烷-3-酮 在 对甲苯磺酸 、 苯 作用下， 生成 3,3-ethylenedioxy-5β-cholestane
  参考文献：
  名称：

  Preparation of Ethylenedioxy Derivatives of Ketosteroids by Exchange Dioxolanation. An Improved Synthesis of Testosterone from Δ⁴-Androstene-3,17-dione¹

  摘要：

  DOI：

  10.1021/ja01634a050

文献信息

• Montmorillonite Clay Catalysis. Part 2.1 An Efficient and Convenient Procedure for the Preparation of Acetals catalysed by Montmorillonite K-10
  作者：Tong-Shuang Li、Sheng-Hui Li、Ji-Tai Li、Hui-Zhang Li

  DOI：10.1039/a605661j

  日期：——

  Acetalization of aldehydes and ketones is catalysed by montmorillonite K-10 in refluxing benzene or toluene in excellent yields.

  醛和酮的缩醛反应在沸腾的苯或甲苯中由膨润土 K-10 催化，产率极高。
• The presence of cholestanyl substituents in hydraphile channels inhibits cation transport in the phospholipid bilayer
  作者：Eric S Meadows、Ernesto Abel-Santos、Daniel C Frankel、George W Gokel

  DOI：10.1016/s0040-4039(00)00068-x

  日期：2000.3

  The presence of steroids within a synthetic, cation channel model compound restricts or prevents the passage of Na+ through the phospholipid bilayer owing to collapse of the pore induced by hydraphobic contacts (C) 2000 Elsevier Science Ltd. All rights reserved.
• Montmorillonite Clay Catalysis. Part 3¹: A New Ready and High Yield Procedure for the Cleavage of Acetals Catalysed by Montmorillonite K 10
  作者：Tong-Shuang Li、Sheng-Hui Li

  DOI：10.1080/00397919708003385

  日期：1997.7

  An easy cleavage of acetals has been carried out in excellent yield under catalysis of montmorillonite K 10 in refluxing wet acetone.
• Preparation of Ethylenedioxy Derivatives of Ketosteroids by Exchange Dioxolanation. An Improved Synthesis of Testosterone from Δ⁴-Androstene-3,17-dione¹
  作者：Hyp J. Dauben、Bjarte Löken、Howard J. Ringold

  DOI：10.1021/ja01634a050

  日期：1954.3