(1S,2S,3R,6S,7R,8R,9R,11S)-3,4,5,6-tetrachloro-13,13-dimethoxy-10,10-diphenylpentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene | 145295-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3R,6S,7R,8R,9R,11S)-3,4,5,6-tetrachloro-13,13-dimethoxy-10,10-diphenylpentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
• CAS: 145295-68-7；145375-77-5
• 化学式: C₂₇H₂₄Cl₄O₂
• 分子量: 522.298
• InChiKey: MOFGAZRAKWUDGM-LJBUZRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  endo-3,3-diphenyltricyclo<3.2.1.0^2,4>oct-6-ene 、 5,5-二甲氧基-1,2,3,4-四氯环戊二烯 以 氘代苯 为溶剂， 反应 72.0h， 以61%的产率得到(1S,2S,3R,6S,7R,8R,9R,11S)-3,4,5,6-tetrachloro-13,13-dimethoxy-10,10-diphenylpentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
  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

• 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
  作者：Mehboob Peeran、James W. Wilt、Ramakrishnan Subramanian、David S. Crumrine

  DOI：10.1021/jo00053a037

  日期：1993.1

  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.