(2-phenylpent-4-enyl)trimethylsilane | 1219613-70-3

• 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-phenylpent-4-enyl)trimethylsilane
• 英文别名: 4-phenyl-5-trimethylsilyl-1-pentene；Trimethyl(2-phenylpent-4-enyl)silane；trimethyl(2-phenylpent-4-enyl)silane
• CAS: 1219613-70-3
• 化学式: C₁₄H₂₂Si
• 分子量: 218.414
• InChiKey: CLEUXGXCPAWOSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  苯乙烯 、 烯丙基三甲基硅烷 在 H⁺-montmorillonite 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以72%的产率得到(2-phenylpent-4-enyl)trimethylsilane
  参考文献：
  名称：

  Heterogeneous Allylsilylation of Aromatic and Aliphatic Alkenes Catalyzed by Proton-Exchanged Montmorillonite

  摘要：

  Allylsilylation of an alkene is the only known procedure to install both silyl and allyl groups onto a carbon-carbon double bond directly. Proton-exchanged montmorillonite showed excellent catalytic performances for the allylsilylation of alkenes. For example, the reaction of p-chlorostyrene with allyltrimethylsilane proceeded smoothly to afford the corresponding allylsilylated product in 95% yield. We also attempted to Isolate the reaction Intermediate on the montmorillonite surface to Investigate the reaction mechanism,

  DOI：

  10.1021/ol100228t

文献信息

• Allylsilylation of alkenes catalyzed by H + -exchanged montmorillonite with water
  作者：Ken Motokura、Shigekazu Matsunaga、Hiroto Noda、Akimitsu Miyaji、Toshihide Baba

  DOI：10.1016/j.cattod.2013.09.058

  日期：2014.5

  Proton-exchanged montmorillonite (H+-montmorillonite) was found to be a heterogeneous catalyst for allylsilylation of alkenes with allylsilanes. A wide variety of aromatic and aliphatic alkenes were effectively converted to the corresponding allylsilylated products in 15-120 min at 60-100 degrees C using H+-montmorillonite with ca. 1-2 wt% of water. The increasing of the amount of water drastically accelerated the allylsilylation of alkenes. For example, the reaction of p-chlorostyrene with allyltrimethysilane afforded 90% yield of the product for 15 min at 40 degrees C using H+-montmorillonite with 8.8 wt% of water, whereas only 2% yield of the product was obtained with 1.3 wt% of water. However, the final product yields with H+-montmorillonite with 1-2 wt% of water were higher than that with the 8.8 wt% of water. A reaction mechanism including the formation of a disilylpropyl cation was proposed. One possible explanation for the role of water is stabilization of the active disilylcation on the montmorillonite surface and/or edges via electron donation from water molecules. (C) 2013 Elsevier B.V. All rights reserved.
• Heterogeneous Allylsilylation of Aromatic and Aliphatic Alkenes Catalyzed by Proton-Exchanged Montmorillonite
  作者：Ken Motokura、Shigekazu Matsunaga、Akimitsu Miyaji、Yasuharu Sakamoto、Toshihide Baba

  DOI：10.1021/ol100228t

  日期：2010.4.2

  Allylsilylation of an alkene is the only known procedure to install both silyl and allyl groups onto a carbon-carbon double bond directly. Proton-exchanged montmorillonite showed excellent catalytic performances for the allylsilylation of alkenes. For example, the reaction of p-chlorostyrene with allyltrimethylsilane proceeded smoothly to afford the corresponding allylsilylated product in 95% yield. We also attempted to Isolate the reaction Intermediate on the montmorillonite surface to Investigate the reaction mechanism,