3',6'-Bis-(4-butoxy-phenylethynyl)-4',5'-dimethyl-[1,1';2',1'']terphenyl | 190372-16-8

• 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: 3',6'-Bis-(4-butoxy-phenylethynyl)-4',5'-dimethyl-[1,1';2',1'']terphenyl
• 英文别名: 1,4-bis[2-(4-butoxyphenyl)ethynyl]-2,3-dimethyl-5,6-diphenylbenzene
• CAS: 190372-16-8
• 化学式: C₄₄H₄₂O₂
• 分子量: 602.816
• InChiKey: YKLXFEHPLAWCTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.79
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3',6'-Bis-(4-butoxy-phenylethynyl)-4',5'-dimethyl-[1,1';2',1'']terphenyl 在 碘 、 silver trifluoromethanesulfonate 作用下， 生成 1,6-Bis-(4-butoxy-phenyl)-3,4-dimethyl-dibenzo[c,g]phenanthrene
  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：

  1,2-二溴-3,6-二碘-4,5-二甲基苯 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 copper(l) iodide 、 二异丙胺 、 三苯基膦 、 potassium iodide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 水 、 硝基苯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 130.0h， 生成 3',6'-Bis-(4-butoxy-phenylethynyl)-4',5'-dimethyl-[1,1';2',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