(E)-2,4-dimethylhex-4-en-3-ol | 116530-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2,4-dimethylhex-4-en-3-ol
• 英文别名: 2,4-dimethyl-hex-4-en-3-ol
• CAS: 116530-51-9
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: DHHMVDDMFQPFDW-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2,4-dimethylhex-4-en-3-ol 在 喹啉 、 盐酸 作用下， 生成 (E)-2,4-dimethyl-hexa-2,4-diene
  参考文献：
  名称：

  Abelmann, Chemische Berichte, 1910, vol. 43, p. 1581

  摘要：

  DOI：
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 、 异丙基氯化镁 以 乙醚 为溶剂， 反应 2.0h， 以90%的产率得到(E)-2,4-dimethylhex-4-en-3-ol
  参考文献：
  名称：

  Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer

  摘要：

  Here we report a ternary catalyst system for the intramolecular hydroamidation of unactivated olefins using simple N-aryl amide derivatives. Amide activation in these reactions occurs via concerted proton-coupled electron transfer (PCET) mediated by an excited state iridium complex and weak phosphate base to furnish a reactive amidyl radical that readily adds to pendant alkenes. A series of H-atom, electron, and proton transfer events with a thiophenol cocatalyst furnish the product and regenerate the active forms of the photocatalyst and base. Mechanistic studies indicate that the amide substrate can be selectively homolyzed via PCET in the presence of the thiophenol, despite a large difference in bond dissociation free energies between these functional groups.

  DOI：

  10.1021/jacs.5b09671

文献信息

• Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer
  作者：David C. Miller、Gilbert J. Choi、Hudson S. Orbe、Robert R. Knowles

  DOI：10.1021/jacs.5b09671

  日期：2015.10.28

  Here we report a ternary catalyst system for the intramolecular hydroamidation of unactivated olefins using simple N-aryl amide derivatives. Amide activation in these reactions occurs via concerted proton-coupled electron transfer (PCET) mediated by an excited state iridium complex and weak phosphate base to furnish a reactive amidyl radical that readily adds to pendant alkenes. A series of H-atom, electron, and proton transfer events with a thiophenol cocatalyst furnish the product and regenerate the active forms of the photocatalyst and base. Mechanistic studies indicate that the amide substrate can be selectively homolyzed via PCET in the presence of the thiophenol, despite a large difference in bond dissociation free energies between these functional groups.
• Abelmann, Chemische Berichte, 1910, vol. 43, p. 1581
  作者：Abelmann

  DOI：——

  日期：——