1-(2,2-dichlorocyclopropyl)butan-1-ol | 151859-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,2-dichlorocyclopropyl)butan-1-ol
• CAS: 151859-80-2
• 化学式: C₇H₁₂Cl₂O
• 分子量: 183.078
• InChiKey: CRLSCKJUEJGBKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(2,2-dichlorocyclopropyl)butan-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到1-Butanoyl-2,2-dichlorocyclopropane
  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
• 作为产物：
  描述：

  2,2-dichlorocyclopropanecarbaldehyde 、 1-碘代丙烷 在 magnesium 作用下， 生成 1-(2,2-dichlorocyclopropyl)butan-1-ol
  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.