α-(trimethylsilyl)vinyl alcohol | 80631-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(trimethylsilyl)vinyl alcohol
• 英文别名: 1-Trimethylsilylethenol
• CAS: 80631-08-9
• 化学式: C₅H₁₂OSi
• 分子量: 116.235
• InChiKey: UPAGHIHJPUIYPE-UHFFFAOYSA-N

物化性质

• 沸点：
  112.6±32.0 °C(Predicted)
• 密度：
  0.834±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-(trimethylsilyl)vinyl alcohol 以 水 为溶剂， 生成 1-(trimethylsilyl)ethanone
  参考文献：
  名称：

  Kresge; Tobin, Journal of the American Chemical Society, 1990, vol. 112, # 7, p. 2805 - 2806

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(三甲基硅基)乙醇 在 丙酮 作用下， 生成 α-(trimethylsilyl)vinyl alcohol
  参考文献：
  名称：

  Acetyltrimethylsilane keto-enol system. Determination of the keto-enol equilibrium constant and acid dissociation constants of the keto and enol forms in aqueous solution

  摘要：

  The enol isomer of the prototype alpha-silyl-substituted ketone, acetyltrimethylsilane, was generated by flash photolytic photooxidation of alpha-(trimethylsilyl)ethanol in aqueous solution, and its rates of acid- and base-catalyzed ketonization in that medium were determined. These, in combination with rates of enolization of the ketone determined by iodine scavenging, provided the keto-enol equilibrium constant pK(E) = 4.89, the dissociation constant of the enol ionizing as an oxygen acid pK(a)E = 11.54, and the dissociation constant of the ketone ionizing as a carbon acid PK(a)K = 16.44. Comparison of these results with corresponding values for simple alkyl-substituted carbonyl compounds shows that alpha-silyl substitution raises K(E) markedly, lowers K(a)E modestly, and raises K(a)K somewhat more strongly. Possible causes of these effects are discussed.

  DOI：

  10.1021/jo00062a004

文献信息

• Kresge; Tobin, Journal of the American Chemical Society, 1990, vol. 112, # 7, p. 2805 - 2806
  作者：Kresge、Tobin

  DOI：——

  日期：——
• KRESGE, A. J.;TOBIN, J. B., J. AMER. CHEM. SOC., 112,(1990) N, C. 2805-2806
  作者：KRESGE, A. J.、TOBIN, J. B.

  DOI：——

  日期：——
• Acetyltrimethylsilane keto-enol system. Determination of the keto-enol equilibrium constant and acid dissociation constants of the keto and enol forms in aqueous solution
  作者：A. J. Kresge、J. B. Tobin

  DOI：10.1021/jo00062a004

  日期：1993.5

  The enol isomer of the prototype alpha-silyl-substituted ketone, acetyltrimethylsilane, was generated by flash photolytic photooxidation of alpha-(trimethylsilyl)ethanol in aqueous solution, and its rates of acid- and base-catalyzed ketonization in that medium were determined. These, in combination with rates of enolization of the ketone determined by iodine scavenging, provided the keto-enol equilibrium constant pK(E) = 4.89, the dissociation constant of the enol ionizing as an oxygen acid pK(a)E = 11.54, and the dissociation constant of the ketone ionizing as a carbon acid PK(a)K = 16.44. Comparison of these results with corresponding values for simple alkyl-substituted carbonyl compounds shows that alpha-silyl substitution raises K(E) markedly, lowers K(a)E modestly, and raises K(a)K somewhat more strongly. Possible causes of these effects are discussed.