(Z)-5-benzyldimethylsilyl-3-phenyl-4-pentenoic acid | 639086-31-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (Z)-5-benzyldimethylsilyl-3-phenyl-4-pentenoic acid
• CAS: 639086-31-0
• 化学式: C₂₀H₂₄O₂Si
• 分子量: 324.495
• InChiKey: DICSSRFKUXXIRF-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-5-benzyldimethylsilyl-3-phenyl-4-pentenoic acid 在 四氯化钛 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以83%的产率得到trans-5-benzyldimethylsilyl-3-phenyl-4-pentanolide
  参考文献：
  名称：

  Acid-catalyzed intramolecular addition of a carboxy group to vinylsilanes

  摘要：

  In the presence of a catalytic amount of (TsOHH2O)-H-. or TiCl4, 5-silyl-4-pentenoic acids (1), namely vinylsilanes with a carboxy group, were smoothly cyclized to gamma-lactones in good to high yields. The difference in the geometry of the carbon-carbon double-bond did not affect the reaction rate. The TiCl4-catalyzed cyclization of the substrates bearing a phenyl or alkyl group at the homoallylic position showed moderate cis-selectivity, while introduction of a substituent into the allylic position led to high transselectivity. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00533-3
• 作为产物：
  描述：

  (Z)-5-benzyldimethylsilyl-3-phenyl-4-penten-1-ol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (Z)-5-benzyldimethylsilyl-3-phenyl-4-pentenoic acid
  参考文献：
  名称：

  Acid-catalyzed intramolecular addition of a carboxy group to vinylsilanes

  摘要：

  In the presence of a catalytic amount of (TsOHH2O)-H-. or TiCl4, 5-silyl-4-pentenoic acids (1), namely vinylsilanes with a carboxy group, were smoothly cyclized to gamma-lactones in good to high yields. The difference in the geometry of the carbon-carbon double-bond did not affect the reaction rate. The TiCl4-catalyzed cyclization of the substrates bearing a phenyl or alkyl group at the homoallylic position showed moderate cis-selectivity, while introduction of a substituent into the allylic position led to high transselectivity. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00533-3