1-methyl-2,3,4,5,6-pentaphenylbenzene | 23934-49-8

• 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: 1-methyl-2,3,4,5,6-pentaphenylbenzene
• 英文别名: methylpentaphenylbenzene；methyl-pentaphenyl-benzene；Methyl-pentaphenyl-benzol；1-Methyl-2,3,4,5,6-pentakis-phenylbenzene
• CAS: 23934-49-8
• 化学式: C₃₇H₂₈
• 分子量: 472.629
• InChiKey: FCTOXAMCYBFKFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-苯基-1-丙炔 、 四苯基环戊二烯酮 生成 1-methyl-2,3,4,5,6-pentaphenylbenzene
  参考文献：
  名称：

  Photolysis of 6-methyl-1,2,3,4,5-pentaphenyl-1,3-cyclohexadiene. Crystal structure of 7-methyl-2,3,5,6-tetraphenyltricyclo[6.4.0.04,8]dodeca-3,5,9,11-tetraene

  摘要：

  DOI：

  10.1021/jo01328a032

文献信息

• ELECTRONIC EFFECTS AND RATES IN THE DIELS-ALDER REACTION
  作者：JOSEPH J. DUDKOWSKI、ERNEST I. BECKER

  DOI：10.1021/jo01136a005

  日期：1952.2
• Photolysis of 6-methyl-1,2,3,4,5-pentaphenyl-1,3-cyclohexadiene. Crystal structure of 7-methyl-2,3,5,6-tetraphenyltricyclo[6.4.0.04,8]dodeca-3,5,9,11-tetraene
  作者：Neil F. Woolsey、Lewis J. Radonovich、Fathi M. Saad、Franklin J. Koch

  DOI：10.1021/jo01328a032

  日期：1979.7
• Structural Features in Crystals of Derivatives of Benzene with Multiple Contiguous Phenyl Substituents
  作者：Eric Gagnon、Thierry Maris、Pierre-Marc Arseneault、Kenneth E. Maly、James D. Wuest

  DOI：10.1021/cg9010746

  日期：2010.2.3

  Hexaphenylbenzene and related derivatives of benzene with multiple contiguous phenyl substituents have well-defined nonplanar topologies. Their structures limit conjugation and disfavor intermolecular pi-pi and C-H center dot center dot center dot pi interactions. Such compounds therefore show higher HOMO-LUMO gaps, lower degrees of self-association, less efficient packing, and higher solubilities than planar analogues. These characteristic properties underlie the growing utility of nonplanar phenyl-substituted benzenes in science and technology. Surprisingly, no systematic structural analysis of compounds of this type has been reported. We have now examined Structural features in crystals of hexaphenylbenzene, 1,2,4,5-tetraphenylbenzene, 1,4-dimethyl-2,3,5,6-tetraphenylbenzene, pentaphenylbenzene, 1-methyl-2,3,4,5,6-pentaphenylbenzene, and an octaphenyl-p-quinquephenyl. These compounds tend to crystallize in sheets held together by van der Waals contacts and small numbers of C-H center dot center dot center dot pi interactions. Although the nonplanar topologies or these compounds do not eliminate C center dot center dot center dot H contacts entirely, the ratios of H center dot center dot center dot H contacts to C center dot center dot center dot H contacts greatly exceed those found in analogous aromatic compounds that can assume planar structures. Our structural analyses promise to help explain the characteristic behavior of nonplanar aryl-substituted arenes and to accelerate the discovery of new applications.