2,4-bis([4-(hexyloxy)phenyl]ethynyl)-1,5-bis(2,2'-bithiophene-5-yl)benzene | 190372-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2,4-bis([4-(hexyloxy)phenyl]ethynyl)-1,5-bis(2,2'-bithiophene-5-yl)benzene
• 英文别名: 2-[2,4-bis[2-(4-hexoxyphenyl)ethynyl]-5-(5-thiophen-2-ylthiophen-2-yl)phenyl]-5-thiophen-2-ylthiophene
• CAS: 190372-10-2
• 化学式: C₅₀H₄₆O₂S₄
• 分子量: 807.178
• InChiKey: INZHISOCYRMQIA-UHFFFAOYSA-N

物化性质

• 沸点：
  864.2±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.32
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,4-bis([4-(hexyloxy)phenyl]ethynyl)-1,5-bis(2,2'-bithiophene-5-yl)benzene 在 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 4,7-bis(4-(hexyloxy)phenyl)-2,10-bis(thiophen-2-yl)bisthien[2,3-a:3',2'-j]anthracene 、 4,8-bis(4-(hexyloxy)phenyl)-2,10-bis(thiophen-2-yl)bisthien[2,3-a:3',2'-j]anthracene
  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 、 正丁基锂 、 硫酸 、 四丁基溴化铵 、 高碘酸 、 二异丙胺 、 potassium iodide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 21.0h， 生成 2,4-bis([4-(hexyloxy)phenyl]ethynyl)-1,5-bis(2,2'-bithiophene-5-yl)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