1-(2-bromoethyl)-1-[1-(2-bromoethyl)-vinyl]-2,2-dichlorocyclopropane | 350991-02-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 1-(2-bromoethyl)-1-[1-(2-bromoethyl)-vinyl]-2,2-dichlorocyclopropane
• 英文别名: 1-(4-Bromobut-1-en-2-yl)-1-(2-bromoethyl)-2,2-dichlorocyclopropane
• CAS: 350991-02-5
• 化学式: C₉H₁₂Br₂Cl₂
• 分子量: 350.908
• InChiKey: SYNGYIQBQXUCGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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-(2-bromoethyl)-1-[1-(2-bromoethyl)-vinyl]-2,2-dichlorocyclopropane 480.0 ℃ 、0.01 Pa 条件下， 以90%的产率得到1,2-bis-(2-bromoethyl)-4,4-dichlorocyclopentene
  参考文献：
  名称：

  Synthesis and anomalous structure–reactivity relationship of 8,11-dichloro[5]metacyclophan-3-one

  摘要：

  The synthesis, structural characterisation, and reactivity of the title compound are reported. It was prepared in order to investigate the effects of incorporation of an sp(2)-centre in the bridge of a [5]metacyclophane on its structure and reactivity. An X-ray crystal structure of the cyclophanone demonstrates that the benzene ring is distorted to the same extent as in the hydrocarbon parent compound, while there is less strain in the bridge. Nevertheless, the cyclophanone displays a reduced reactivity in Diels-Alder reactions, which is tentatively ascribed to transition state effects. Calculations indicate that in spite of the close proximity between the ketone functionality and the benzene ring, there are no pi-pi interactions between them. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00239-3
• 作为产物：
  描述：

  [3,4-Dimethylidene-6-(4-methylphenyl)sulfonyloxyhexyl] 4-methylbenzenesulfonate 在 potassium tert-butylate 、 lithium bromide 作用下， 以 丙酮 、 正戊烷 为溶剂， 反应 10.0h， 生成 1-(2-bromoethyl)-1-[1-(2-bromoethyl)-vinyl]-2,2-dichlorocyclopropane
  参考文献：
  名称：

  Synthesis and anomalous structure–reactivity relationship of 8,11-dichloro[5]metacyclophan-3-one

  摘要：

  The synthesis, structural characterisation, and reactivity of the title compound are reported. It was prepared in order to investigate the effects of incorporation of an sp(2)-centre in the bridge of a [5]metacyclophane on its structure and reactivity. An X-ray crystal structure of the cyclophanone demonstrates that the benzene ring is distorted to the same extent as in the hydrocarbon parent compound, while there is less strain in the bridge. Nevertheless, the cyclophanone displays a reduced reactivity in Diels-Alder reactions, which is tentatively ascribed to transition state effects. Calculations indicate that in spite of the close proximity between the ketone functionality and the benzene ring, there are no pi-pi interactions between them. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00239-3