p-Toluoyltriphenylsilane | 124494-19-5

• 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-Toluoyltriphenylsilane
• 英文别名: (4-Methylphenyl)-triphenylsilylmethanone
• CAS: 124494-19-5
• 化学式: C₂₆H₂₂OSi
• 分子量: 378.546
• InChiKey: XPDXPXLWBPCPNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  487.3±28.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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-Toluoyltriphenylsilane 在 吡啶 、 4-二甲氨基吡啶 、 potassium fluoride 、 双氧水 、 potassium hydrogencarbonate 、 二乙醇胺 、 (-)-diisopinocamphenylborane chloride 作用下， 反应 17.5h， 生成 (R)-(4-Methylphenyl)phenylmethanol
  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
• 作为产物：
  描述：

  三苯基氯硅烷 、 对甲基苯甲酰氯 生成 p-Toluoyltriphenylsilane
  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

文献信息

• The conversion of acyl silanes into chiral secondary alcohols
  作者：John D. Buynak、J. Byron Strickland、Trace Hurd、Andrew Phan

  DOI：10.1039/c39890000089

  日期：——

  Chiral secondary carbinols are prepared in high enantiomeric excess by a new process involving the reduction of acyl silanes and utilising a thermal rearrangement of α-acetoxy silanes.

  通过涉及减少酰基硅烷并利用α-乙酰氧基硅烷的热重排的新方法，以高对映体过量制备手性仲甲醇。
• BUYNAK, JOHN D.;STRICKLAND, J. BYRON;HURD, TRACE;PHAN, ANDREW, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 89-90
  作者：BUYNAK, JOHN D.、STRICKLAND, J. BYRON、HURD, TRACE、PHAN, ANDREW

  DOI：——

  日期：——
• Thermal rearrangements of .alpha.-(acyloxy)silanes: formation of chiral precursors and migratory preference of silicon-based groups
  作者：John D. Buynak、J. Byron Strickland、Grady W. Lamb、Dipti Khasnis、Seema Modi、Delena Williams、Hongming Zhang

  DOI：10.1021/jo00025a024

  日期：1991.12

  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.