1-trimethylsilyl-3-phenylcyclopropene | 865351-11-7

• 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: 1-trimethylsilyl-3-phenylcyclopropene
• 英文别名: Trimethyl-(3-phenylcyclopropen-1-yl)silane
• CAS: 865351-11-7
• 化学式: C₁₂H₁₆Si
• 分子量: 188.345
• InChiKey: AOJFBXOMVABGKD-UHFFFAOYSA-N

物化性质

• 沸点：
  219.9±39.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  1-trimethylsilyl-3-phenylcyclopropene 以 乙醚 、 苯 为溶剂， 反应 36.0h， 生成 2-phenyl-3-(2-phenyl-3-(trimethylsilyl)cyclopropyl)-4-(trimethylsilyl)tricyclo[3.2.1.0(2,4)]oct-6-ene
  参考文献：
  名称：

  Stereocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene

  摘要：

  1-Trimethylsilyl-3-phenylcyclopropene undergoes a highly stereocontrolled ene-reaction to give a dimer and further reaction leads to one or more trimers derived through two ene-reactions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.111
• 作为产物：
  描述：

  三甲基-[(E)-2-苯乙烯基]硅烷 在 sodium hydroxide 、 甲基锂 、 十六烷基三甲基溴化铵 作用下， 生成 1-trimethylsilyl-3-phenylcyclopropene
  参考文献：
  名称：

  Stereocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene

  摘要：

  1-Trimethylsilyl-3-phenylcyclopropene undergoes a highly stereocontrolled ene-reaction to give a dimer and further reaction leads to one or more trimers derived through two ene-reactions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.111

文献信息

• Generation and stereocontrolled trapping of 3-phenylcyclopropene and its derivatives
  作者：Andrey E. Sheshenev、Mark S. Baird、Anna K. Croft、Ivan G. Bolesov

  DOI：10.1070/mc2004v014n06abeh002061

  日期：2004.1

  Selective methods for the preparation of 3-phenylcyclopropene and its 1-substituted derivatives are provided. The parent cyclopropene is readily trapped in (3+2)- and (4+2)-cycloadditions that lead to exo-3-phenyl-1,2-disubstituted cyclopropanes. Ab initio calculations suggest that the lowest energy conformation has the plane of the benzene ring perpendicular to the cyclopropene π-bond but with a low

  提供了制备3-苯基环丙烯及其1-取代的衍生物的选择性方法。母体环丙烯很容易陷入（3 + 2）-和（4 + 2）-环加成反应中，从而导致exo-3-苯基-1,2-二取代的环丙烷。从头算计算表明最低的能量构象具有垂直于环丙烯π键的苯环平面，但旋转势垒较低。
• Stereo- and regiocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene
  作者：Andrey E. Sheshenev、Mark S. Baird、Ivan G. Bolesov、Alexandre S. Shashkov

  DOI：10.1016/j.tet.2009.10.077

  日期：2009.12

  1-Trimethylsilyl-3-phenylcyclopropene and its 2D-analog undergo a highly stereocontrolled ene-reaction to give a single dinner. Further reaction leads to one or more trimers derived through two ene-reactions. The dinner formed easily undergoes cycloaddition with active dienes and nitrile oxides while the trimers do not react under the same conditions. The first enantioselective example of an ene-reaction of cyclopropene derivatives using optically active 1-trimethylsilyl-3S-phenylcyclopropene is also discussed. (C) 2009 Elsevier Ltd. All rights reserved.