trans-2-Hydroxymethyl-bicyclopropyl | 192056-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2-Hydroxymethyl-bicyclopropyl
• 英文别名: (2-Cyclopropylcyclopropyl)methanol；(2-cyclopropylcyclopropyl)methanol
• CAS: 192056-12-5
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: QENGFKJBIVRULH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二碘甲烷 、 2,4-戊二烯-1-醇 在 diethylzinc 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以87%的产率得到trans-2-Hydroxymethyl-bicyclopropyl
  参考文献：
  名称：

  Studies on Mercury(II)-Mediated Opening of Bi- and Tercyclopropane Arrays

  摘要：

  The first examples of the mercury(II)-mediated ring opening of bicyclopropane and tercyclopropane arrays have been investigated. The presence of an adjacent cyclopropyl group dramatically increased the rate of the mercury-mediated opening of the first cyclopropane in a cyclopropane array. In contrast to the mercury-mediated ring opening of monocyclopropanes which usually undergo a concerted ring-opening mechanism, electrophilic openings of cyclopropane arrays occurred through a stabilized, free carbocation. Excellent regio- and stereoselectivities were observed in the mercury-mediated intramolecular openings of the second cyclopropanes in the cyclopropane arrays, giving rise to the formation of enantiomerically pure, highly substituted tetrahydrofurans.

  DOI：

  10.1021/jo970464o

文献信息

• Studies on Mercury(II)-Mediated Opening of Bi- and Tercyclopropane Arrays
  作者：Anthony G. M. Barrett、William Tam

  DOI：10.1021/jo970464o

  日期：1997.7.1

  The first examples of the mercury(II)-mediated ring opening of bicyclopropane and tercyclopropane arrays have been investigated. The presence of an adjacent cyclopropyl group dramatically increased the rate of the mercury-mediated opening of the first cyclopropane in a cyclopropane array. In contrast to the mercury-mediated ring opening of monocyclopropanes which usually undergo a concerted ring-opening mechanism, electrophilic openings of cyclopropane arrays occurred through a stabilized, free carbocation. Excellent regio- and stereoselectivities were observed in the mercury-mediated intramolecular openings of the second cyclopropanes in the cyclopropane arrays, giving rise to the formation of enantiomerically pure, highly substituted tetrahydrofurans.