4',4'-dimethylspiro<1,3-dioxolane-2,3'-cholest-5'-ene> | 35490-52-9

• 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: 4',4'-dimethylspiro<1,3-dioxolane-2,3'-cholest-5'-ene>
• 英文别名: 4,4-dimethyl-3,3-ethylenedioxycholest-5-ene；4',4'-dimethylspiro(1,3-dioxolane-2,3'-cholest-5'-ene)；(8'S,9'S,10'R,13'R,14'S,17'R)-4',4',10',13'-tetramethyl-17'-[(2R)-6-methylheptan-2-yl]spiro[1,3-dioxolane-2,3'-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene]
• CAS: 35490-52-9
• 化学式: C₃₁H₅₂O₂
• 分子量: 456.753
• InChiKey: YDHSEWDBWYEIHG-NCCRCWGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  4',4'-dimethylspiro<1,3-dioxolane-2,3'-cholest-5'-ene> 在 Montmorillonite K 10 、 水 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以98%的产率得到4,4-dimethyl-cholest-5-en-3-one
  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：

  4,4-dimethyl-cholest-5-en-3-one 、 乙二醇 在 montmorillonite K-10 作用下， 以 苯 为溶剂， 反应 5.0h， 以96%的产率得到4',4'-dimethylspiro<1,3-dioxolane-2,3'-cholest-5'-ene>
  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

• Chemical Consequences of Long-Range Orbital Interactions in Cholestane-3,7-diol Monosulfonate Esters. A Seven-Center Fragmentation
  作者：Petrus M. F. M. Bastiaansen、Ladislav Kohout、Maarten A. Posthumus、Joannes B. P. A. Wijnberg、Aede de Groot

  DOI：10.1021/jo951655z

  日期：1996.1.1

  The manifestation of through-five-bond interactions in the reactions of the rigid 1,5-diol monosulfonate esters (1-3), having an ideal all-trans geometry of the sigma-relay, with sodium tert-amylate is investigated. It has been shown that the deprotonation of the alcohol group in 2 and 3, which results in an increased electrofugal ability of this group, finds expression in a seven-center fragmentation. This fragmentation also illustrates that effective through-five-bond interactions exist between the alcoholate group and the carbocationic center which is generated during the heterolysis. The reaction outcome of mesylate 1 does not indicate effective through-bond interactions, and only elimination is observed. This difference can be attributed to the alkyl substituents on the gamma- and alpha-positions to the mesylate group in 2 and 3, respectively, which stimulate the seven-center fragmentation. Though a reasonable amount of fragmentation product is obtained from 3, the through-five-bond interaction is not strong enough to dominate the reaction course completely and typical El-like processes, i.e., elimination and rearrangement, are competitive. As expected, only a 1,2 Me-shift is observed in the reaction of the axial mesylate 4 where a gauche interaction is present in the geometry of the sigma-relay. The presence of through-bond interactions in the reactions of 3 and 4 becomes apparent by comparison of the reactivity of 3 and 4 with their O-silylated analogs 5 and 6.
• 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。
• 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.