trans-1,1-dibromo-2-trimethylsilyl-3-phenylcyclopropane

• 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: trans-1,1-dibromo-2-trimethylsilyl-3-phenylcyclopropane
• 英文别名: [(1R,3R)-2,2-dibromo-3-phenylcyclopropyl]-trimethylsilane
• 化学式: C₁₂H₁₆Br₂Si
• 分子量: 348.153
• InChiKey: HMLWQXKANOBERD-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  trans-1,1-dibromo-2-trimethylsilyl-3-phenylcyclopropane 在 甲基锂 作用下， 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：

  三溴甲烷 、 三甲基-[(E)-2-苯乙烯基]硅烷 在 sodium hydroxide 、 十六烷基三甲基溴化铵 作用下， 以90%的产率得到trans-1,1-dibromo-2-trimethylsilyl-3-phenylcyclopropane
  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

• Versatile Synthesis of Cyclopropanecarboxylic Acid Derivatives by the Ni(CO)₄-Induced Reductive Carbonylation Reaction of<i>gem</i>-Dibromocyclopropanes
  作者：Toshikazu Hirao、Yoshiyuki Harano、Yoshihiro Yamana、Yuji Hamada、Shinichiro Nagata、Toshio Agawa

  DOI：10.1246/bcsj.59.1341

  日期：1986.5

  Reductive carbonylation of gem-dibromocyclopropanes was achieved by treatment with tetracarbonylnickel in the presence of alcohols, amines, thiols, or imidazole in DMF leading to the corresponding cyclopropanecarboxylic acid derivatives, respectively. Use of disulfides as an initial nucleophile resulted in carbonylation with sulfenylation at the geminal position. This method was applied to the intramolecular

  在醇、胺、硫醇或咪唑的存在下，在 DMF 中用四羰基镍处理，分别产生相应的环丙烷羧酸衍生物，从而实现嵴二溴环丙烷的还原羰基化。使用二硫化物作为初始亲核试剂导致在孪位位置发生羰基化和磺基化。该方法应用于2,2-二溴环丙烷醇分子内还原羰基化反应生成双环内酯。镍卡宾和烯醇复合物被认为是关键中间体。
• HIRAO, TOSHIKAZU;MASUNAGA, TOSHIO;HAYASHI, KEN-ICHIRO;OHSHIRO, YOSHIKI, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1987) N 7, 1277-1279
  作者：HIRAO, TOSHIKAZU、MASUNAGA, TOSHIO、HAYASHI, KEN-ICHIRO、OHSHIRO, YOSHIKI

  DOI：——

  日期：——
• 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.
• Stereocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene
  作者：Andrey E. Sheshenev、Mark S. Baird、Anna K. Croft、Zoya A. Starikova、Alexandre S. Shashkov、Alexey L. Zhuze、Ivan G. Bolesov

  DOI：10.1016/j.tetlet.2005.12.111

  日期：2006.4

  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.