trans-1,1-dibromo-2,3-dipentylcyclopropane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: trans-1,1-dibromo-2,3-dipentylcyclopropane
• 英文别名: (2R,3R)-1,1-dibromo-2,3-dipentylcyclopropane
• 化学式: C₁₃H₂₄Br₂
• 分子量: 340.142
• InChiKey: AOLGKDBAAAPRND-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• 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：

  正丁基锂 、 trans-1,1-dibromo-2,3-dipentylcyclopropane 在 溴丁基-镁 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.17h， 以77%的产率得到r-1-butyl-2-c,3-t-dipentylcyclopropane
  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
• 作为产物：
  描述：

  (6E)-6-十二碳烯 、 三溴甲烷 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 trans-1,1-dibromo-2,3-dipentylcyclopropane
  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

• 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.