dicyclohexyl(dibromomethyl)methylsilane | 190653-00-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: dicyclohexyl(dibromomethyl)methylsilane
• 英文别名: Dicyclohexyl-(dibromomethyl)-methylsilane
• CAS: 190653-00-0
• 化学式: C₁₄H₂₆Br₂Si
• 分子量: 382.254
• InChiKey: DDVAIWDDBUTPML-UHFFFAOYSA-N

物化性质

• 沸点：
  370.0±22.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  溴丁基-镁 、 dicyclohexyl(dibromomethyl)methylsilane 在 manganese(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到(E)-1-dicyclohexylmethylsilyl-1-pentene
  参考文献：
  名称：

  三烷基（二溴甲基）硅烷或 1,2-双（二溴甲基）苯与三有机锰酸盐的反应。烯基硅烷和 1,2-二芳基-1,2-二氢苯并环丁烯的简便和选择性合成

  摘要：

  用衍生自氯化锰 (II) 和三摩尔量的格氏试剂或烷基锂的三烷基锰酸盐处理三烷基（二溴甲基）硅烷，以良好的收率提供具有高立体选择性的（E）-1-三烷基甲硅烷基-1-烯烃。三烷基（二溴甲基）硅烷与烷基卤化镁的反应在催化量的氯化锰（II）存在下进行。用三苯基锰酸盐处理 1,2-双(二溴甲基)苯得到 1,2-二苯基-1,2-二氢苯并环丁烯。

  DOI：

  10.1246/bcsj.73.2139
• 作为产物：
  描述：

  di(cyclohexyl)methylchlorosilane 、 二溴甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 dicyclohexyl(dibromomethyl)methylsilane
  参考文献：
  名称：

  Reactions ofgem-Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds

  摘要：

  The reaction of gem-dibromocyclopropanes 5 with nBu(3)MgLi affords butylated cyclopropylmagnesium species that can be trapped with various electrophiles. The reaction of dibromomethylsilanes 12 requires the addition of a catalytic amount of CuCN.2LiCl for smooth migration of the alkyl groups. The resultant alpha-silylpentylmagnesium compounds 16 react with electrophiles, such as acyl chlorides or alpha.beta-unsaturated ketones to afford alpha- or gamma-silyl ketones, respectively. Treatment of dibromodisilylmethanes with Me3MgLi yields 1-bromo-1,1-disilylethanes 25 that can be converted into 1,1-disilylethenes 29 by dehydrobromination.

  DOI：

  10.1002/1521-3765(20020402)8:7<1730::aid-chem1730>3.0.co;2-6

文献信息

• Manganese-catalyzed reaction of gem-dibromoalkanes with Grignard reagents. Selective synthesis of alkenylsilanes
  作者：Hirotada Kakiya、Rie Inoue、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1016/s0040-4039(97)00601-1

  日期：1997.5

  Treatment of dibromomethyltrialkylsilanes with butylmagnesium bromide in the presence of a catalytic amount of manganese(II) chloride provided (E)-1-trialkylsilyl-1-pentenes with high stereoselectivity in good yields.

  在催化量的氯化锰（II）的存在下，用丁基溴化镁处理二溴甲基三烷基硅烷，可提供高立体选择性的高收率的（E）-1-三烷基甲硅烷基-1-戊烯。
• Alkylative Preparation ofα-Silylalkylmagnesium from R3SiCHBr2 Using a Magnesate Reagent
  作者：Junichi Kondo、Atsushi Inoue、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1002/1521-3773(20010601)40:11<2085::aid-anie2085>3.0.co;2-k

  日期：2001.6.1

  Magnesium-bromine exchange to provide the 1-bromo-1-silylmethylmagnesium species is mediated by treatment of dibromomethylsilane with an trialkylmagnesate reagent. The addition of a copper catalyst induces facile migration of an alkyl group to afford an α-silylalkylmagnesium compound, which furnishes α-silyl ketones in good yield upon treatment with acyl chloride.
• Reaction of Trialkyl(dibromomethyl)silanes or 1,2-Bis(dibromomethyl)benzene with Triorganomanganates. A Facile and Selective Synthesis of Alkenylsilanes and 1,2-Diaryl-1,2-dihydrobenzocyclobutenes
  作者：Hirotada Kakiya、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1246/bcsj.73.2139

  日期：2000.9

  stereoselectivity in good yields. The reaction of trialkyl(dibromomethyl)silanes with alkylmagnesium halides proceeded in the presence of a catalytic amount of manganese(II) chloride. Treatment of 1,2-bis(dibromomethyl)benzene with triphenylmanganate gave 1,2-diphenyl-1,2-dihydrobenzocyclobutene.

  用衍生自氯化锰 (II) 和三摩尔量的格氏试剂或烷基锂的三烷基锰酸盐处理三烷基（二溴甲基）硅烷，以良好的收率提供具有高立体选择性的（E）-1-三烷基甲硅烷基-1-烯烃。三烷基（二溴甲基）硅烷与烷基卤化镁的反应在催化量的氯化锰（II）存在下进行。用三苯基锰酸盐处理 1,2-双(二溴甲基)苯得到 1,2-二苯基-1,2-二氢苯并环丁烯。
• Reactions ofgem-Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds
  作者：Atsushi Inoue、Junichi Kondo、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1002/1521-3765(20020402)8:7<1730::aid-chem1730>3.0.co;2-6

  日期：2002.4.2

  The reaction of gem-dibromocyclopropanes 5 with nBu(3)MgLi affords butylated cyclopropylmagnesium species that can be trapped with various electrophiles. The reaction of dibromomethylsilanes 12 requires the addition of a catalytic amount of CuCN.2LiCl for smooth migration of the alkyl groups. The resultant alpha-silylpentylmagnesium compounds 16 react with electrophiles, such as acyl chlorides or alpha.beta-unsaturated ketones to afford alpha- or gamma-silyl ketones, respectively. Treatment of dibromodisilylmethanes with Me3MgLi yields 1-bromo-1,1-disilylethanes 25 that can be converted into 1,1-disilylethenes 29 by dehydrobromination.