3,3-dichloro-c-5-ethenyl-t-2-methyl-r-1-cyclopentanecarbonitrile

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3-dichloro-c-5-ethenyl-t-2-methyl-r-1-cyclopentanecarbonitrile
• 化学式: C₉H₁₁Cl₂N
• 分子量: 204.099
• InChiKey: IDIKCKZKBBQHKK-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  反式-巴豆腈(含有约20的顺式同分异构体) 、 2,2-二氯环丙基乙烯 在 偶氮二异丁腈 、 二苯二硫醚 作用下， 以 苯 为溶剂， 生成 3,3-dichloro-5-ethenyl-2-methyl-1-cyclopentanecarbonitrile 、 3,3-dichloro-t-5-ethenyl-c-2-methyl-r-1-cyclopentanecarbonitrile 、 3,3-dichloro-c-5-ethenyl-t-2-methyl-r-1-cyclopentanecarbonitrile
  参考文献：
  名称：

  2,2-Dihalovinylcyclopropanes as highly diastereoselective three-atom addends in phenylthio radical mediated vinylcyclopentane synthesis

  摘要：

  2,2-Dichloro- or -2,2-dibromovinylcyclopropane was condensed with electron-deficient alkenes in a phenylthio radical catalyzed process to afford 4-substituted and 4,5-disubstituted-1,1-dihalo-3-vinylcyclopentane derivatives in good yield and with good-to-excellent diastereoselectivity for the 3,4-cis isomer. Neither electron-rich nor beta-substituted alkenes led to good yields of cyclopentane products. The diastereoselectivity and reactivity profiles of these transformations are satisfactorily rationalized by application of existing transition-state application of existing transition-state models of radical reactions.

  DOI：

  10.1021/ja00077a040

文献信息

• 2,2-Dihalovinylcyclopropanes as highly diastereoselective three-atom addends in phenylthio radical mediated vinylcyclopentane synthesis
  作者：Ken S. Feldman、Heidi M. Berven、Paul H. Weinreb

  DOI：10.1021/ja00077a040

  日期：1993.12

  2,2-Dichloro- or -2,2-dibromovinylcyclopropane was condensed with electron-deficient alkenes in a phenylthio radical catalyzed process to afford 4-substituted and 4,5-disubstituted-1,1-dihalo-3-vinylcyclopentane derivatives in good yield and with good-to-excellent diastereoselectivity for the 3,4-cis isomer. Neither electron-rich nor beta-substituted alkenes led to good yields of cyclopentane products. The diastereoselectivity and reactivity profiles of these transformations are satisfactorily rationalized by application of existing transition-state application of existing transition-state models of radical reactions.