3-(t-butyl)diphenylsiloxy-androstan-17-one | 400643-64-3

• 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-(t-butyl)diphenylsiloxy-androstan-17-one
• 英文别名: (3S,5S,8R,9S,10S,13S,14S)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CAS: 400643-64-3
• 化学式: C₃₅H₄₈O₂Si
• 分子量: 528.85
• InChiKey: RYVFQNOBUKWOAQ-YCHMFCEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(t-butyl)diphenylsiloxy-androstan-17-one 在 platinum on activated charcoal sodium tetrahydroborate 、 potassium tert-butylate 、 氢气 、 二甲基氯化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3R,5S,6S)-6-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-[tert-butyl(diphenyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-3-propan-2-ylheptane-1,5-diol
  参考文献：
  名称：

  香豆甾醇侧链的立体控制合成

  摘要：

  该contignasterol的侧链（的四款车型2 - 5）已准备立体专一。合成中的关键反应是类固醇衍生物6与拟对映异构醛7和8之间的氯化二甲基铝介导的“烯”反应。

  DOI：

  10.1016/s0040-4039(01)01964-5
• 作为产物：
  描述：

  3-(t-butyl)diphenylsiloxy-17-methoxyandrostane 在 三氯乙腈 、 间氯过氧苯甲酸 作用下， 以 乙腈 为溶剂， 反应 24.5h， 以59%的产率得到3-(t-butyl)diphenylsiloxy-androstan-17-one
  参考文献：
  名称：

  CCl₃CN: A Crucial Promoter of mCPBA-Mediated Direct Ether Oxidation

  摘要：

  The direct oxidation of ether sp(3) C-H bonds using the new reagent system mCPBA/CCl3CN/MeCN has been developed. CCl3CN in MeCN drastically alters the reactivity of m-chloroperbenzoic acid (mCPBA), and chemoselective transformation of methyl ethers to ketones was realized under mild conditions. Radical-based mCPBA-mediated oxidation was suggested as the reaction mechanism. The present new reaction expands the utility of methyl ethers as stable synthetic precursors of carbonyl compounds and of mCPBA as a radical-based C-H oxidizing agent.

  DOI：

  10.1021/ol1018079

文献信息

• One-pot reductive cleavage of exo-olefin to methylene with a mild ozonolysis-Clemmensen reduction sequence
  作者：Shu Xu、Takayuki Toyama、Jun Nakamura、Hirokazu Arimoto

  DOI：10.1016/j.tetlet.2010.06.102

  日期：2010.8

  A one-pot exo-olefin reductive cleavage was for the first time developed. The reaction could proceed under a mild condition avoiding the use of hazardous and expensive reagents. Meanwhile, a TMSCl-mediated Clemmensen reduction in alcoholic solvent was also examined. (C) 2010 Elsevier Ltd. All rights reserved.
• CCl₃CN: A Crucial Promoter of <i>m</i>CPBA-Mediated Direct Ether Oxidation
  作者：Shin Kamijo、Shoko Matsumura、Masayuki Inoue

  DOI：10.1021/ol1018079

  日期：2010.9.17

  The direct oxidation of ether sp(3) C-H bonds using the new reagent system mCPBA/CCl3CN/MeCN has been developed. CCl3CN in MeCN drastically alters the reactivity of m-chloroperbenzoic acid (mCPBA), and chemoselective transformation of methyl ethers to ketones was realized under mild conditions. Radical-based mCPBA-mediated oxidation was suggested as the reaction mechanism. The present new reaction expands the utility of methyl ethers as stable synthetic precursors of carbonyl compounds and of mCPBA as a radical-based C-H oxidizing agent.
• Stereocontrolled synthesis of contignasterol's side chain
  作者：Irene Izzo、Vincenza Pironti、Carmela Della Monica、Guido Sodano、Francesco De Riccardis

  DOI：10.1016/s0040-4039(01)01964-5

  日期：2001.12

  The four models of the contignasterol's side chains (2–5) have been stereospecifically prepared. The key reaction in the synthesis is a dimethylaluminum chloride-mediated ‘ene’ reaction between the steroid derivative 6 and the pseudo-enantiomeric aldehydes 7 and 8.

  该contignasterol的侧链（的四款车型2 - 5）已准备立体专一。合成中的关键反应是类固醇衍生物6与拟对映异构醛7和8之间的氯化二甲基铝介导的“烯”反应。