1-(cyclohexa-2,5-dienylmethyloxy)-naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(cyclohexa-2,5-dienylmethyloxy)-naphthalene
• 英文别名: 1-(Cyclohexa-2,5-dien-1-ylmethoxy)naphthalene
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: PXTACRFEKOZPKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,4-环己二烯 、 1,2-二乙炔基-3-甲氧基苯 在 1,4-环己二烯 作用下， 以 氯苯 为溶剂， 反应 5.0h， 以48%的产率得到1-甲氧基萘
  参考文献：
  名称：

  Ortho Effect in the Bergman Cyclization:  Interception of p-Benzyne Intermediate by Intramolecular Hydrogen Abstraction

  摘要：

  Intramolecular hydrogen atom (H-atom) abstraction from the o-OCH3 group effectively intercepts the p-benzyne intermediate in the Bergman cycloaromatization of 2,3-diethynyl-1-methoxybenzene (1) before this intermediate undergoes either retro-Bergman ring opening or external H-atom abstraction. This process leads to the formation of a new diradical and renders the cyclization step essentially irreversible. Chemical and kinetic consequences of this phenomenon were investigated through the combination of computational and experimental studies.

  DOI：

  10.1021/jo051857n

文献信息

• Ortho Effect in the Bergman Cyclization:  Interception of <i>p</i>-Benzyne Intermediate by Intramolecular Hydrogen Abstraction
  作者：Tarek A. Zeidan、Mariappan Manoharan、Igor V. Alabugin

  DOI：10.1021/jo051857n

  日期：2006.2.1

  Intramolecular hydrogen atom (H-atom) abstraction from the o-OCH3 group effectively intercepts the p-benzyne intermediate in the Bergman cycloaromatization of 2,3-diethynyl-1-methoxybenzene (1) before this intermediate undergoes either retro-Bergman ring opening or external H-atom abstraction. This process leads to the formation of a new diradical and renders the cyclization step essentially irreversible. Chemical and kinetic consequences of this phenomenon were investigated through the combination of computational and experimental studies.