p-Toluoyldiphenyl-tert-butylsilane | 137122-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-Toluoyldiphenyl-tert-butylsilane
• 英文别名: [Tert-butyl(diphenyl)silyl]-(4-methylphenyl)methanone
• CAS: 137122-47-5
• 化学式: C₂₄H₂₆OSi
• 分子量: 358.555
• InChiKey: WGOVTHPAVKVQAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  p-Toluoyldiphenyl-tert-butylsilane 在 titanium(IV) isopropylate 、 diethylzinc 、 盐酸 作用下， 以 乙醚 、 正己烷 、 水 为溶剂， 反应 12.0h， 以59%的产率得到(tert-butyldiphenylsilyl)(p-tolyl)methanol
  参考文献：
  名称：

  A Lewis acid-promoted reduction of acylsilanes to α-hydroxysilanes by diethylzinc

  摘要：

  We report here the first example of the reduction of acylsilanes to alpha-hydroxysilanes, in which diethylzinc was used as a highly reactive agent in the presence of Ti(OiPr)(4) or other Lewis acids. The reduction typically proceeds to give synthetically useful alpha-hydroxysilanes in good yields. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.059
• 作为产物：
  描述：

  对甲基苯甲酰氯 、 叔丁基二苯基氯硅烷 生成 p-Toluoyldiphenyl-tert-butylsilane
  参考文献：
  名称：

  Thermal rearrangements of .alpha.-(acyloxy)silanes: formation of chiral precursors and migratory preference of silicon-based groups

  摘要：

  The asymmetric reduction of acylsilanes to chiral alpha-hydroxysilanes and the thermal rearrangement of the corresponding chiral alpha-acetoxysilanes was explored. IpcBCl reduces many acylsilanes in > 95% ee. The rate of the thermal rearrangement of the alpha-acetoxysilanes was dependent upon the substituents at both silicon and carbon. Evidence is presented to indicate there is electron deficiency at the alpha-carbon in the transition state. Migratory aptitudes follow those expected on the basis of the migrating group assuming an apical migratory group at a pentacoordinate silicon. A previously unreported hydrolytic transformation of a proposed acylsilyl hydride to a stable 1-sila-1,2-diol was observed.

  DOI：

  10.1021/jo00025a024