2,3-O-isopropylidene-14-O-(trimethylsilyl)poststerone | 23931-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-14-O-(trimethylsilyl)poststerone
• 英文别名: (1R,2R,4S,8R,10R,14S,17S,18R)-17-acetyl-2,6,6,18-tetramethyl-14-trimethylsilyloxy-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icos-12-en-11-one
• CAS: 23931-34-2
• 化学式: C₂₇H₄₂O₅Si
• 分子量: 474.713
• InChiKey: RPPQTRNMSSYYNL-YHLZAIQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-14-O-(trimethylsilyl)poststerone 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.55h， 生成 (20RS)-2β,3β-dihydroxy-14α,20-bis(trimethylsiloxy)-20-(trifluoromethyl)-5β-pregn-7-en-6-one
  参考文献：
  名称：

  First Example of Trifluoromethylation in the Ecdysteroid Series. Synthesis of (20RS)-20-O-Hydro-20-trifluoromethylpoststerone

  摘要：

  The title compound was synthesized by trifluoromethylation of poststerone derivatives with trimethyl(trifluoromethyl)silane in the presence of tetrabutylammonium fluoride.

  DOI：

  10.1023/b:rujo.0000019736.80902.6e
• 作为产物：
  描述：

  (2β,3β,5β,14xi)-2,3,14-三羟基孕-7-烯-6,20-二酮 在 phosphomolybdic acid 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.38h， 生成 2,3-O-isopropylidene-14-O-(trimethylsilyl)poststerone
  参考文献：
  名称：

  First Example of Trifluoromethylation in the Ecdysteroid Series. Synthesis of (20RS)-20-O-Hydro-20-trifluoromethylpoststerone

  摘要：

  The title compound was synthesized by trifluoromethylation of poststerone derivatives with trimethyl(trifluoromethyl)silane in the presence of tetrabutylammonium fluoride.

  DOI：

  10.1023/b:rujo.0000019736.80902.6e

文献信息

• Stereoselective synthesis of 9α-hydroxylated ecdysteroids
  作者：Svetlana V. Drach、Vladimir A. Khripach、Raisa P. Litvinovskaya、Alexander S. Lyakhov、Bernd Schneider、Halina A. Zhylitskaya

  DOI：10.1016/j.steroids.2009.10.011

  日期：2010.2

  Treatment of ecdysteroids with excess of TBAF in THF was shown to proceed with stereoselective oxidation at the 9 alpha position of the carbon skeleton. The stereochemistry of the products was confirmed by X-ray analysis. Using this method. 9 alpha-hydroxyecdysteroids were obtained in good yield. The results open a route to novel type of natural and modified steroids that are difficult to access otherwise. (C) 2009 Elsevier Inc. All rights reserved.
• ——
  作者：V. N. Odinokov、R. G. Savchenko、S. R. Nazmeeva、I. V. Galyautdinov

  DOI：10.1023/a:1021393611323

  日期：——

  In the reactions of poststerone derivatives and 20-hydroxyecdysone with (trifluoromethyl)trimethylsilane catalyzed by tetrabutylammonium fluoride, the 14alpha-hydroxy group is readily subjected to trimethylsilylation.