4-(trimethylsilyl)-2-methyl-d3-2-butanol-1,1,1-d3 | 245764-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(trimethylsilyl)-2-methyl-d3-2-butanol-1,1,1-d3
• CAS: 245764-70-9
• 化学式: C₈H₂₀OSi
• 分子量: 166.284
• InChiKey: AUBGBBZESZXOCM-WFGJKAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  10.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(trimethylsilyl)-2-methyl-d3-2-butanol-1,1,1-d3 在 盐酸 作用下， 以 水 为溶剂， 反应 0.25h， 以55%的产率得到4-(trimethylsilyl)-2-chloro-2-methyl-butane-3,3-d2
  参考文献：
  名称：

  γ-Silyl-stabilized tertiary ions? Solvolysis of­4-(trimethylsilyl)-2-chloro-2-methylbutane

  摘要：

  Rate constant, isotope-effect, and product studies of the solvolysis of 4-(trimethylsilyl)-2-chloro-2-methylbutane, 11, and its carbon analog, 2-chloro-2,5,5-trimethylhexane, 10, in aqueous ethanol and aqueous 2,2,2-trifluoroethanol (TFE) indicate very little participation of the gamma-silyl substituent. These results are in sharp contrast to earlier reports on secondary gamma-silyl substituted systems, in which the beck lobe of the silicon-carbon bond has been shown to overlap with the carbocation p-orbital to form a so-called 'percaudally' stabilized intermediate. While the solvolytic behaviors of 11 and 10 are nearly identical in ethanol, differences in the TFE lead to the conclusion that there is a minor amount of participation by the silyl substituent in that solvent. Interestingly, this observation lends credence to an earlier suggestion that TFE is better than ethanol at stabilizing more highly delocalized ions. Copyright (C) 1999 John Wiley st Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199907)12:7<564::aid-poc164>3.0.co;2-2
• 作为产物：
  描述：

  乙基3-(三甲基硅基)丙酸酯 、 (Methyl-d3)magnesium iodide 以 乙醚 为溶剂， 反应 1.5h， 以74%的产率得到4-(trimethylsilyl)-2-methyl-d3-2-butanol-1,1,1-d3
  参考文献：
  名称：

  γ-Silyl-stabilized tertiary ions? Solvolysis of­4-(trimethylsilyl)-2-chloro-2-methylbutane

  摘要：

  Rate constant, isotope-effect, and product studies of the solvolysis of 4-(trimethylsilyl)-2-chloro-2-methylbutane, 11, and its carbon analog, 2-chloro-2,5,5-trimethylhexane, 10, in aqueous ethanol and aqueous 2,2,2-trifluoroethanol (TFE) indicate very little participation of the gamma-silyl substituent. These results are in sharp contrast to earlier reports on secondary gamma-silyl substituted systems, in which the beck lobe of the silicon-carbon bond has been shown to overlap with the carbocation p-orbital to form a so-called 'percaudally' stabilized intermediate. While the solvolytic behaviors of 11 and 10 are nearly identical in ethanol, differences in the TFE lead to the conclusion that there is a minor amount of participation by the silyl substituent in that solvent. Interestingly, this observation lends credence to an earlier suggestion that TFE is better than ethanol at stabilizing more highly delocalized ions. Copyright (C) 1999 John Wiley st Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199907)12:7<564::aid-poc164>3.0.co;2-2