1,1,2,2-Tetraphenyl-3-(2,2-dicyanovinyl)cyclopropane | 72228-09-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1,2,2-Tetraphenyl-3-(2,2-dicyanovinyl)cyclopropane
• 英文别名: 2-[(2,2,3,3-Tetraphenylcyclopropyl)methylidene]propanedinitrile；2-[(2,2,3,3-tetraphenylcyclopropyl)methylidene]propanedinitrile
• CAS: 72228-09-2
• 化学式: C₃₁H₂₂N₂
• 分子量: 422.529
• InChiKey: ALKIZHUEJTWPTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,1,3,3-Tetraphenyl-5,5-dicyano-1,4-pentadiene 在 苯乙酮 作用下， 以 苯 为溶剂， 生成 1,1,2,2-Tetraphenyl-3-(2,2-dicyanovinyl)cyclopropane
  参考文献：
  名称：

  Unusual organic photochemistry effected by cyano and methoxy substitution. Exploratory and mechanistic organic photochemistry

  摘要：

  DOI：

  10.1021/ja00515a035

文献信息

• Photochemistry of Organic Molecules Entwined in Spiderwebs; The Use of Poly(methyl methacrylate) Glass for Restricting Excited-State Motion
  作者：Howard E. Zimmerman、Michael E. O'Brien

  DOI：10.1021/jo00086a036

  日期：1994.4

  A study of several unimolecular photochemical rearrangements in poly(methyl methacrylate) glass was carried out with the intent of comparing the behavior of excited-state species trapped in a polymer matrix with both the corresponding solution photochemistry and that in crystal lattices. Three reactants were studied: (a) 4,5,5-triphenylcyclohex-2-en-1-one, (b) 1,1-dicyano-3,3,5,5-tetraphenyl-1,4-pentadiene, and (c) 2,2-dimethyl-1,1-diphenyl-3-(2,2-diphenyl)cyclopropane. The solution photochemistry of the three compounds had previously been studied in our laboratory, and the photochemistry in the crystal lattice had been similarly investigated for the first two. The crystal lattice photochemistry of the last of the three was investigated in the present study. For each of the three reactants; different photochemical behavior was observed depending on the environment-polymer glass, solution, or crystal lattice. The experimental behavior correlated nicely with theoretical assessment of molecular motion of the component atoms in proceeding onward from that point along the reaction coordinate where multiple reaction pathways are available. The preferred reaction pathway proved consistently to require the least motion and the minimum molecular volume displacement. A concept of least motion dependent on its application to the ''branch point'' rather than the entire conversion of reactant to product was established.
• Unusual organic photochemistry effected by cyano and methoxy substitution. Exploratory and mechanistic organic photochemistry
  作者：Howard E. Zimmerman、Diego Armesto、Mercedes G. Amezua、Thomas P. Gannett、Richard P. Johnson

  DOI：10.1021/ja00515a035

  日期：1979.10