1,4-Bis[2,5-bis[2-(4-butoxyphenyl)ethynyl]-4-(2,5-dimethylphenyl)phenyl]-2,5-dimethylbenzene | 203254-23-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,4-Bis[2,5-bis[2-(4-butoxyphenyl)ethynyl]-4-(2,5-dimethylphenyl)phenyl]-2,5-dimethylbenzene
• CAS: 203254-23-3
• 化学式: C₈₄H₈₂O₄
• 分子量: 1155.57
• InChiKey: QXNPRLMJRUKWQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.6
• 重原子数：
  88
• 可旋转键数：
  28
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-Bis[2,5-bis[2-(4-butoxyphenyl)ethynyl]-4-(2,5-dimethylphenyl)phenyl]-2,5-dimethylbenzene 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到8-butoxy-4,6a-dimethyl-{[5,8-dimethyl-9-(4-butoxyphenyl)]phenanthro[2,3-c]}spiro[{[2'-(4-butoxyphenyl)][4-(4-butoxyphenyl)-5,8-dimethylnaphtho[1,2-f']]}indenyl-1',6-(6,6a-dihydrofluoranthene)]
  参考文献：
  名称：

  Synthesis of Ethynyl-Substituted Quinquephenyls and Conversion to Extended Fused-Ring Structures

  摘要：

  An organometallic coupling, electrophile-induced cyclization strategy for the synthesis of p-terphenyl compounds has been extended to the synthesis of p-quinquephenyl systems. In this work we report the synthesis of various polycyclic aromatic systems containing nine annelated rings including the synthesis of functionalized polycyclic aromatic systems. An interesting side reaction which leads to an indenyl spiro ring system is also described. This side reaction can be suppressed by changing the electrophile (from H+ to I+) or by modification of the cyclization precursor. The UV-vis and fluorescence spectra of several of these polycyclic aromatics and the p-quinquephenyl precursors are also reported.

  DOI：

  10.1021/jo9721251
• 作为产物：
  描述：

  1,4-二碘-2,5-二甲苯 、 2,5-bis(4-butoxyphenylethynyl)-2',5'-dimethyl-1,1'-biphenyl-4-boronic acid 在 氢氧化钾 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯基膦 作用下， 以 水 、 硝基苯 为溶剂， 反应 14.0h， 以82.1%的产率得到1,4-Bis[2,5-bis[2-(4-butoxyphenyl)ethynyl]-4-(2,5-dimethylphenyl)phenyl]-2,5-dimethylbenzene
  参考文献：
  名称：

  Synthesis of Ethynyl-Substituted Quinquephenyls and Conversion to Extended Fused-Ring Structures

  摘要：

  An organometallic coupling, electrophile-induced cyclization strategy for the synthesis of p-terphenyl compounds has been extended to the synthesis of p-quinquephenyl systems. In this work we report the synthesis of various polycyclic aromatic systems containing nine annelated rings including the synthesis of functionalized polycyclic aromatic systems. An interesting side reaction which leads to an indenyl spiro ring system is also described. This side reaction can be suppressed by changing the electrophile (from H+ to I+) or by modification of the cyclization precursor. The UV-vis and fluorescence spectra of several of these polycyclic aromatics and the p-quinquephenyl precursors are also reported.

  DOI：

  10.1021/jo9721251

文献信息

• Synthesis of Ethynyl-Substituted Quinquephenyls and Conversion to Extended Fused-Ring Structures
  作者：Marc B. Goldfinger、Khushrav B. Crawford、Timothy M. Swager

  DOI：10.1021/jo9721251

  日期：1998.3.1

  An organometallic coupling, electrophile-induced cyclization strategy for the synthesis of p-terphenyl compounds has been extended to the synthesis of p-quinquephenyl systems. In this work we report the synthesis of various polycyclic aromatic systems containing nine annelated rings including the synthesis of functionalized polycyclic aromatic systems. An interesting side reaction which leads to an indenyl spiro ring system is also described. This side reaction can be suppressed by changing the electrophile (from H+ to I+) or by modification of the cyclization precursor. The UV-vis and fluorescence spectra of several of these polycyclic aromatics and the p-quinquephenyl precursors are also reported.