2,5-bis(4-dodecyloxyphenylethynyl)-4'-methoxy-1,1'-biphenyl-4-boronic acid

• 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: 2,5-bis(4-dodecyloxyphenylethynyl)-4'-methoxy-1,1'-biphenyl-4-boronic acid
• 英文别名: [2,5-Bis[2-(4-dodecoxyphenyl)ethynyl]-4-(4-methoxyphenyl)phenyl]boronic acid
• 化学式: C₅₃H₆₉BO₅
• 分子量: 796.939
• InChiKey: XUKLUPFTTCKZRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.44
• 重原子数：
  59
• 可旋转键数：
  31
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-二碘苯 、 2,5-bis(4-dodecyloxyphenylethynyl)-4'-methoxy-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， 以87.1%的产率得到1-[4-[2,5-Bis[2-(4-dodecoxyphenyl)ethynyl]-4-(4-methoxyphenyl)phenyl]phenyl]-2,5-bis[2-(4-dodecoxyphenyl)ethynyl]-4-(4-methoxyphenyl)benzene
  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.