2-<(Trimethylsilyl)methyl>styrene | 134261-73-7

• 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: 2-<(Trimethylsilyl)methyl>styrene
• 英文别名: a-Trimethylsilylmethyl-styrene；(2-ethenylphenyl)methyl-trimethylsilane
• CAS: 134261-73-7
• 化学式: C₁₂H₁₈Si
• 分子量: 190.36
• InChiKey: WDKFUDYJYQSTKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-(2-bromophenyl)-1,3-dithiolane 在 bis-triphenylphosphine-palladium(II) chloride 、 bis(triphenylphosphine)nickel(II) chloride 作用下， 以 乙醚 、 苯 为溶剂， 反应 32.0h， 生成 2-<(Trimethylsilyl)methyl>styrene
  参考文献：
  名称：

  Nickel-catalyzed olefination of cyclic benzylic dithioacetals by Grignard reagents. Scope and mechanism

  摘要：

  The details of the first nickel-catalyzed olefination of cyclic dithioacetals to form substituted styrenes and aryl-substituted 1,4-pentadienes are described. The reaction represents a new synthetic use of the dithioacetal functionality. Only nickel complexes catalyzed these cross-coupling reactions; palladium complexes displayed no catalytic activity under the reaction conditions employed. Selective coupling occurred. A mechanism for the reaction is proposed. The experimental evidence indicates that, in these nickel-catalyzed couplings, cyclic dithioacetals are more reactive than their acyclic analogues. This increased reactivity appears to be the result of maintaining the two sulfur atoms in close proximity to each other by the use of a short chain of methylene groups.

  DOI：

  10.1021/jo00012a043

文献信息

• Nickel-catalyzed olefination of cyclic benzylic dithioacetals by Grignard reagents. Scope and mechanism
  作者：Zhi Jie Ni、Nai Wen Mei、Xian Shi、Yih Ling Tzeng、Maw Cherng Wang、Tien Yau Luh

  DOI：10.1021/jo00012a043

  日期：1991.6

  The details of the first nickel-catalyzed olefination of cyclic dithioacetals to form substituted styrenes and aryl-substituted 1,4-pentadienes are described. The reaction represents a new synthetic use of the dithioacetal functionality. Only nickel complexes catalyzed these cross-coupling reactions; palladium complexes displayed no catalytic activity under the reaction conditions employed. Selective coupling occurred. A mechanism for the reaction is proposed. The experimental evidence indicates that, in these nickel-catalyzed couplings, cyclic dithioacetals are more reactive than their acyclic analogues. This increased reactivity appears to be the result of maintaining the two sulfur atoms in close proximity to each other by the use of a short chain of methylene groups.