(3E)-2-methyl-4-(2,6-dimethylphenyl)-3-buten-2-ol | 441003-43-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (3E)-2-methyl-4-(2,6-dimethylphenyl)-3-buten-2-ol
• 英文别名: (E)-4-(2,6-dimethylphenyl)-2-methylbut-3-en-2-ol
• CAS: 441003-43-6
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: ONIUTDWROHHLMA-CMDGGOBGSA-N

物化性质

• 沸点：
  304.3±11.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (3E)-2-methyl-4-(2,6-dimethylphenyl)-3-buten-2-ol 在 正丁基锂 、 四甲基乙二胺 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.25h， 生成 2-[(E)-1-deuterio-3-methoxy-3-methylbut-1-enyl]-1,3-dimethylbenzene
  参考文献：
  名称：

  Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene

  摘要：

  The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. In this paper, the full details of the examples of the highly activated vinyl hydrogens in twisted styrene derivatives are described, with a discussion on the correlation between the reactivity of the vinyl hydrogens and the magnitude of the twist. The highly reactive vinyl hydrogens could be rationalized by considering the novel orbital interaction between the pi* orbital of the benzene ring and the sigma orbital of the vinylic C-H bond in the twisted styrene derivatives.

  DOI：

  10.1021/jo061092z
• 作为产物：
  描述：

  1-(2,6-dimethylphenyl)-3-methyl-1-butyn-3-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到(3E)-2-methyl-4-(2,6-dimethylphenyl)-3-buten-2-ol
  参考文献：
  名称：

  Vinyl hydrogen more reactive than benzyl hydrogen toward base in significantly twisted styrenes

  摘要：

  The novel example of vinyl hydrogen more reactive than benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. The characteristic nature of the vinyl hydrogen, which is activated by sigma-pi* orbital interaction, was apparently demonstrated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00308-2

文献信息

• Vinyl hydrogen more reactive than benzyl hydrogen toward base in significantly twisted styrenes
  作者：Hajime Mori、Takafumi Matsuo、Yasunori Yoshioka、Shigeo Katsumura

  DOI：10.1016/s0040-4039(01)00308-2

  日期：2001.4

  The novel example of vinyl hydrogen more reactive than benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. The characteristic nature of the vinyl hydrogen, which is activated by sigma-pi* orbital interaction, was apparently demonstrated. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene
  作者：Hajime Mori、Takafumi Matsuo、Yasunori Yoshioka、Shigeo Katsumura

  DOI：10.1021/jo061092z

  日期：2006.11.1

  The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. In this paper, the full details of the examples of the highly activated vinyl hydrogens in twisted styrene derivatives are described, with a discussion on the correlation between the reactivity of the vinyl hydrogens and the magnitude of the twist. The highly reactive vinyl hydrogens could be rationalized by considering the novel orbital interaction between the pi* orbital of the benzene ring and the sigma orbital of the vinylic C-H bond in the twisted styrene derivatives.