2,5-bis(4-chlorophenyl)-3,4-diphenylcyclopenta-2,4-dienone | 38268-04-1

• 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: 2,5-bis(4-chlorophenyl)-3,4-diphenylcyclopenta-2,4-dienone
• 英文别名: 2,5-bis-(4-chloro-phenyl)-3,4-diphenyl-cyclopentadienone；2,5-Bis-(4-chlor-phenyl)-3,4-diphenyl-cyclopentadienon；2,5-bis(4-chlorophenyl)-3,4-diphenylcyclopenta-2,4-dien-1-one
• CAS: 38268-04-1
• 化学式: C₂₉H₁₈Cl₂O
• 分子量: 453.367
• InChiKey: GSVDNDUTJHQKQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-二氟氯苯 、 2,5-bis(4-chlorophenyl)-3,4-diphenylcyclopenta-2,4-dienone 在 溴苯 作用下， 生成 3,6-bis-(4-chloro-phenyl)-4,5-diphenyl-phthalic acid-anhydride
  参考文献：
  名称：

  The Absorption Spectra of Some Chloro-Substituted Tetracyclones

  摘要：

  DOI：

  10.1021/ja01145a078
• 作为产物：
  描述：

  2-(4-氯苯基)-1-苯乙酮 在 sodium methylate 、 溶剂黄146 、 N,N-二甲基-4-亚硝基苯胺 、 锌 、 苯 作用下， 生成 2,5-bis(4-chlorophenyl)-3,4-diphenylcyclopenta-2,4-dienone
  参考文献：
  名称：

  Tetraarylcyclopentadienes¹

  摘要：

  DOI：

  10.1021/ja01609a053

文献信息

• Efficient Synthesis of Substituted Polyarylphthalimides via Cycloaddition of Cyclopentadienones with 2-Bromomaleimide
  作者：Jacques Einhorn、Rémi Vanel、Florian Berthiol、Bernard Bessières、Cathy Einhorn

  DOI：10.1055/s-0030-1260556

  日期：2011.6

  Functionalized tetraarylphthalimides or diarylphthal­imides fused with an acenaphthene moiety have been prepared in one step from 2-bromomaleimide and tetraarylcyclopentadienones (tetracyclones) or 7,9-diaryl-8H-cyclopentacenaphthylene-8-ones (acecyclones). The reaction, involving a cycloaddition-decarbonylation-dehydrobromination sequence, gives high isolated yields and is compatible with the presence of various functional groups.

  已通过一步法合成了带有acenaphthene结构的功能化四芳基邻苯二甲酰亚胺或二芳基邻苯二甲酰亚胺。利用2-溴马来酰亚胺与四芳基环戊二烯酮（四环酮）或7,9-二芳基-8H-环戊并苊-8-酮（苊环酮）反应制得。该反应涉及环加成-脱羰基-脱溴化氢序列，具有高纯度产率，且能兼容多种官能团的存在。
• Predicting the UV−Vis Spectra of Tetraarylcyclopentadienones:  Using DFT Molecular Orbital Energies to Model Electronic Transitions of Organic Materials
  作者：Robert G. Potter、Thomas S. Hughes

  DOI：10.1021/jo701676x

  日期：2008.4.1

  Tetraphenylcyclopentadienone, due to its intrinsically low HOMO-LUMO gap, has been suggested as a valuable repeat unit in conducting polymers for nanoscale electronics. The HOMO and LUMO of tetraphenylcyclopentadienone appear to be associated with the relevant pi orbitals of unsubstituted cyclopentadienone. Using previously developed carbonylative coupling reactions, a series of tetraarylcyclopentadienones was synthesized, accessing a range of substituents not previously available. The UV-vis spectra of these molecules were compared to their calculated wave functions and predicted transitions. A quantitative structure-activity relationship was discovered that may greatly simplify prediction of band gaps for oligomers and polymers built from these tetraarylcyclopentadienones.
• Broser,W. et al., Chemische Berichte, 1969, vol. 102, p. 1715 - 1724
  作者：Broser,W. et al.

  DOI：——

  日期：——