Propenoyltriphenylsilane | 137122-53-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Propenoyltriphenylsilane
• 英文别名: Triphenylsilyl vinyl ketone；1-triphenylsilylprop-2-en-1-one
• CAS: 137122-53-3
• 化学式: C₂₁H₁₈OSi
• 分子量: 314.459
• InChiKey: WQVHAHUZQMJDRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-1-(Triphenylsilyl)prop-2-en-1-ol	137122-54-4	C21H20OSi	316.475

反应信息

• 作为反应物：
  描述：

  Propenoyltriphenylsilane 在 二乙醇胺 、 (-)-diisopinocamphenylborane chloride 作用下， 生成 (S)-1-Triphenylsilanyl-prop-2-en-1-ol 、 (R)-1-(Triphenylsilyl)prop-2-en-1-ol
  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 、 3-[2-(乙烯基氧基)乙氧基]-1-丙烯 生成 Propenoyltriphenylsilane
  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

• 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.