(8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]螺[1,2,4,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-3,2'-1,3-二氧戊环] | 3496-88-6

• 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
• 中文名称: (8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]螺[1,2,4,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-3,2'-1,3-二氧戊环]
• 英文名称: Δ5-cholesten-3-one ethylene ketal
• 英文别名: 3,3-Ethylenedioxycholest-5-ene；(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]spiro[1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]
• CAS: 3496-88-6
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: GPAYFLROALHUFV-OKPKYCIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]螺[1,2,4,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-3,2'-1,3-二氧戊环] 在 aluminium(III) iodide 作用下， 以 乙腈 、 苯 为溶剂， 反应 0.08h， 以92%的产率得到4-胆甾烯-3-酮
  参考文献：
  名称：

  将缩酮选择性转化为羰基化合物的简便方法

  摘要：

  缩酮被三碘化铝（Al3 3）选择性裂解为相应的羰基化合物，收率很高。但是，硫缩酮不受该试剂的影响。

  DOI：

  10.1016/s0040-4039(01)80779-6
• 作为产物：
  描述：

  4-胆甾烯-3-酮 、 乙二醇 在 montmorillonite K-10 作用下， 以 苯 为溶剂， 反应 2.0h， 以98%的产率得到(8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]螺[1,2,4,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-3,2'-1,3-二氧戊环]
  参考文献：
  名称：

  Montmorillonite Clay Catalysis. Part 2.1 An Efficient and Convenient Procedure for the Preparation of Acetals catalysed by Montmorillonite K-10

  摘要：

  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。

  DOI：

  10.1039/a605661j

文献信息

• A Convenient Synthesis of 5,6β-Epoxides of Some Cholesteryl Esters and Δ⁵-Ketosteroid Derivatives by Catalytic β-Stereoselective Epoxidation
  作者：Jean-Claude Marchon、René Ramasseul

  DOI：10.1055/s-1989-27261

  日期：——

  The epoxidation of a series of cholesteryl esters by air in the presence of a catalytic amount of a ruthenium tetramesitylporphyrin complex is described. The preparative procedure, which requires only 4 to 5 mol % of the catalyst, leads to high conversion (76 to 94 %) and very high β-stereoselectivity (> 99 %). Similar results are obtained in the epoxidation of 3β-acetoxyandrost-5-ene-17-one, 3β-acetoxypregn-5-ene-20-one, and 3,3-ethylenedioxycholest-5-ene.

  报道了在四甲基卟啉钌络合物催化剂存在下，空气对一系列胆固醇酯进行环氧化反应的研究。该制备方法仅需加入4至5摩尔%的催化剂，即可实现高转化率（76至94%）和极高β立体选择性（> 99%）。类似的结果也在3β-乙酰氧基雄甾-5-烯-17-酮、3β-乙酰氧基孕甾-5-烯-20-酮和3,3-亚乙二氧基胆甾-5-烯的环氧化反应中获得。
• Dichlororuthenium(IV) Complex ofmeso-Tetrakis(2,6-dichlorophenyl)porphyrin: Active and Robust Catalyst for Highly Selective Oxidation of Arenes, Unsaturated Steroids, and Electron-Deficient Alkenes by Using 2,6-DichloropyridineN-Oxide
  作者：Jun-Long Zhang、Chi-Ming Che

  DOI：10.1002/chem.200401008

  日期：2005.6.20

  under acid-free conditions, a wide variety of hydrocarbons including 1) cycloalkenes, conjugated enynes, electron-deficient alkenes (to afford epoxides), 2) arenes (to afford quinones), and 3) Delta5-unsaturated steroids, Delta4-3-ketosteroids, and estratetraene derivatives (to afford epoxide/ketone derivatives of steroids) in up to 99 % product yield within several hours with up to 100 % substrate conversion

  由[Ru（VI）（2,6-Cl2tpp）O2]与Me3SiCl的反应以90％的收率制备的[Ru（IV）（2,6-Cl2tpp）Cl2]是通过X射线晶体学表征的结构明显优于[Ru（IV）（tmp）Cl2]，[Ru（IV）（ttp）Cl2]和[Ru（II）（por）（CO）]（por = 2,6-Cl2tpp，F20-tpp ，F28-tpp）作为烯烃与2,6-Cl2pyNO（2,6-Cl2tpp = meso-tetrakis（2,6-dichlorophenyl）porphyrinato dianion; tmp = meso-tetramesitylporphyrinato dianion; ttp = meso-tetrakis（对甲苯基）卟啉二价阴离子; F20-tpp =间四（五氟苯基）卟啉二价阴离子; F28-tpp = 2,3,7,8,12,13,17,18-八氟-5,10,15
• BIS(DIISOBUTYLALUMINUM) 1,2-ETHANEDITHIOLATE: A REAGENT IN THE CONVERSION OF OXYACETALS TO THIOACETALS
  作者：TsuyoShi Satoh、Satoru Uwaya、Koji Yamakawa

  DOI：10.1246/cl.1983.667

  日期：1983.5.5

  Bis(diisobutylaluminum) 1,2-ethanedithiolate (9) made from diisobutylaluminum hydride and ethanedithiol in benzene is useful to convert oxyacetals into thioacetals, however not effective to ketones.

  双（二异丁基铝）1,2-乙二硫醇（9）由氢化二异丁基铝和乙二硫醇在苯中制成，可用于将氧乙酸酯转化为硫代乙酸酯，但对酮类无效。
• Highly β‐Selective Epoxidation of Δ ⁵ ‐Unsaturated Steroids Catalyzed by Ketones
  作者：Dan Yang、Guan‐Sheng Jiao

  DOI：10.1002/1521-3765(20001002)6:19<3517::aid-chem3517>3.0.co;2-#

  日期：2000.10.2

  A general catalytic and environmentally friendly method for beta-epoxidation of Delta(5)-unsaturated steroids has been developed, which uses ketones as the catalysts and Oxone as the terminal oxidant. A whole range of Delta(5)-unsaturated steroids, which bear different functional groups such as hydroxyl, carbonyl, acetyl, or ketal, as well as different side chains, were conveniently converted to the corresponding synthetically and biologically interesting 5 beta,5 beta-epoxides with excellent beta-selectivities and high yields.
• The Hydration of Unsaturated Steroids by the Brown Hydroboration Reaction. I. Monounsaturated Steroids
  作者：Manasse Nussim、Yehuda Mazur、Franz Sondheimer

  DOI：10.1021/jo01028a032

  日期：1964.5