1,5-dibromo-2,4-bis(p-dodecyloxyphenylethynyl)benzene | 190372-01-1

• 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: 1,5-dibromo-2,4-bis(p-dodecyloxyphenylethynyl)benzene
• 英文别名: 1,5-dibromo-2,4-bis-(4-dodecyloxyphenylethynyl)benzene；1,5-Dibromo-2,4-bis[2-(4-dodecoxyphenyl)ethynyl]benzene
• CAS: 190372-01-1
• 化学式: C₄₆H₆₀Br₂O₂
• 分子量: 804.789
• InChiKey: DWLYCTRMOSOCFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  779.1±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  18.5
• 重原子数：
  50
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-dibromo-2,4-bis(p-dodecyloxyphenylethynyl)benzene 、 苯硼酸 在 氢氧化钾 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 水 、 硝基苯 为溶剂， 反应 16.0h， 以80.9%的产率得到4',6'-Bis-(4-dodecyloxy-phenylethynyl)-[1,1';3',1'']terphenyl
  参考文献：
  名称：

  Directed Electrophilic Cyclizations:  Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics

  摘要：

  A versatile method for the synthesis of complex, fused polycyclic aromatic systems in high chemical yield is described. Construction is achieved using a general two-step synthetic sequence. Pd-catalyzed Suzuki and Negishi type cross-coupling chemistries allow for the preparation of nonfused skeletal ring systems in yields consistently > 80%. The critical ring-forming step, which generally proceeds in very high to quantitative yield, utilizes 4-alkoxyphenylethynyl groups and is induced by strong electrophiles such as trifluoroacetic acid and iodonium tetrafluoroborate. The reaction in essence produces phenanthrene moieties which are integrated into extended polycyclic aromatic structures. Fused polycyclic benzenoids as well as benzenoid/thiophene systems may be prepared utilizing this methodology. The scope of the described cross-coupling/cyclization chemistry including mechanistic insights and problematic side reactions are described.

  DOI：

  10.1021/ja9642673
• 作为产物：
  描述：

  1,3-二溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 硫酸 、 四丁基溴化铵 、 高碘酸 、 二异丙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.5h， 生成 1,5-dibromo-2,4-bis(p-dodecyloxyphenylethynyl)benzene
  参考文献：
  名称：

  Directed Electrophilic Cyclizations:  Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics

  摘要：

  A versatile method for the synthesis of complex, fused polycyclic aromatic systems in high chemical yield is described. Construction is achieved using a general two-step synthetic sequence. Pd-catalyzed Suzuki and Negishi type cross-coupling chemistries allow for the preparation of nonfused skeletal ring systems in yields consistently > 80%. The critical ring-forming step, which generally proceeds in very high to quantitative yield, utilizes 4-alkoxyphenylethynyl groups and is induced by strong electrophiles such as trifluoroacetic acid and iodonium tetrafluoroborate. The reaction in essence produces phenanthrene moieties which are integrated into extended polycyclic aromatic structures. Fused polycyclic benzenoids as well as benzenoid/thiophene systems may be prepared utilizing this methodology. The scope of the described cross-coupling/cyclization chemistry including mechanistic insights and problematic side reactions are described.

  DOI：

  10.1021/ja9642673

文献信息

• Chan, Julian M. W.; Tischler, Jonathan R.; Kooi, Steve E., Journal of the American Chemical Society, 2009, vol. 131, p. 5659 - 5666
  作者：Chan, Julian M. W.、Tischler, Jonathan R.、Kooi, Steve E.、Bulovic, Vladimir、Swager, Timothy M.

  DOI：——

  日期：——
• Synthesis of arylethynylated cyclohexa-m-phenylenes via sixfold Suzuki coupling
  作者：Julian M.W. Chan、Timothy M. Swager

  DOI：10.1016/j.tetlet.2008.05.150

  日期：2008.8

  A one-step, one-pot assembly of arylethynylated cyclohexa-m-phenylenes from meta-dibromide and meta-diboronic acids has been accomplished using a sixfold Suzuki macrocyclization, without the need for high dilution or slow-addition techniques. (C) 2008 Elsevier Ltd. All rights reserved.