| 127414-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• CAS: 127414-16-8
• 化学式: C₂₀H₁₈
• 分子量: 258.363
• InChiKey: PKLPQDORATZVPZ-BHOZUIHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  endo-3,3-diphenyltricyclo<3.2.1.0^2,4>oct-6-ene 在 偶氮二异庚腈 、 溴 、 三正丁基氢锡 作用下， 以 四氯化碳 、 氘代苯 为溶剂， 生成
  参考文献：
  名称：

  Aryl .pi. participation in additions and solvolyses of endo-3,3-diphenyltricyclo[3.2.1.02,4]oct-6-ene and -oct-6-yl systems

  摘要：

  The influence of phenyl pi electrons on the strategically located double bond of the endo-3,3-diphenyltricyclo[3.2.1.0(2,4)]oct-6-ene (1) during cycloaddition, electrophilic addition, epoxidation, reduction, cyclopropanation, and radical addition has been investigated both through product identification and relative rate studies. Similar additions to the isomeric exo-3,3-diphenyltricyclo[3.2.1.0(2,4)]oct-6-ene (2) serve as a mechanistic contrast to the reactions of 1. This is the first system that appears to demonstrate radical-initiated LRAMERO (long-range aryl migration with electrocyclic ring opening). Solvolyses of the exo and endo tosylates derived from 1 are also influenced by the underlying phenyl group.

  DOI：

  10.1021/jo00053a037

文献信息

• ? Participation in addition reactions of endo-3,3-diphenyltricyclo[3.2.1.02,4]oct-6-ene
  作者：Mehboob Peeran、James W. Wilt、Subramanian Ramakrishnan、David S. Crumrine

  DOI：10.1039/c39890001906

  日期：——

  Radical initiated LRAMERO (long range aryl migration coupled with electrophilic ring opening) is one example of π participation occurring from the syn phenyl ring of (1) in both electrophilic and radical addition reactions.

  自由基引发的LRAMERO（长距离芳基迁移与亲电子开环偶联）是在亲电子和自由基加成反应中由（1）的合成苯环发生的π参与的一个实例。