2-[Tert-butyl(dimethyl)silyl]-2-methylsulfanyl-1-phenylethanone | 1027643-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[Tert-butyl(dimethyl)silyl]-2-methylsulfanyl-1-phenylethanone
• 英文别名: 2-[tert-butyl(dimethyl)silyl]-2-methylsulfanyl-1-phenylethanone
• CAS: 1027643-43-1
• 化学式: C₁₅H₂₄OSSi
• 分子量: 280.506
• InChiKey: PTVGDJDQRXPHSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (dimethyl(phenyl)silyl)(phenyl)methanone 、 (Bis-methylsulfanyl-methyl)-tert-butyl-dimethyl-silane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 61.0h， 以42%的产率得到2-[Tert-butyl(dimethyl)silyl]-2-methylsulfanyl-1-phenylethanone
  参考文献：
  名称：

  1,2- versus 1,3-Silyl migration in the reaction of acylsilanes with silyl-substituted carbanions

  摘要：

  The Peterson olefination of acylsilanes 1 by silylated carbanions 5,14 to give alkenes 13,17 via a 1,3-silyl shift is favored by the stabilization of the carbanion intermediate 16 through two sulfide units versus one as in 12, while a combination of DMPS on I and TBS on 14 leads to 1,2-migration product 15. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.02.077

文献信息

• 1,2- versus 1,3-Silyl migration in the reaction of acylsilanes with silyl-substituted carbanions
  作者：Thomas Puschke、Jens Lange、Ernst Schaumann

  DOI：10.1016/j.tetlet.2008.02.077

  日期：2008.4

  The Peterson olefination of acylsilanes 1 by silylated carbanions 5,14 to give alkenes 13,17 via a 1,3-silyl shift is favored by the stabilization of the carbanion intermediate 16 through two sulfide units versus one as in 12, while a combination of DMPS on I and TBS on 14 leads to 1,2-migration product 15. (C) 2008 Published by Elsevier Ltd.