1-(3'',5''-dimethoxyphenyl)-2-(2'-thienyl)pyrrole | 849403-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(3'',5''-dimethoxyphenyl)-2-(2'-thienyl)pyrrole
• 英文别名: 1-(3,5-Dimethoxyphenyl)-2-thiophen-2-ylpyrrole
• CAS: 849403-54-9
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: DBQUSPNETFPGGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四氰基乙烯 、 1-(3'',5''-dimethoxyphenyl)-2-(2'-thienyl)pyrrole 以 N,N-二甲基甲酰胺 为溶剂， 以37%的产率得到1-(3'',5''-dimethoxyphenyl)-2-(2'-thienyl)-5-tricyanovinylpyrrole
  参考文献：
  名称：

  Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

  摘要：

  Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2'-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryi-2-(2'-thienyl)pyrroles 2 using TCNE. The tricyanovinyl-derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities beta of the mentioned compounds. The beta values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.062
• 作为产物：
  描述：

  3-(2-噻吩甲酰基)丙酸 在 劳森试剂 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 168.25h， 生成 1-(3'',5''-dimethoxyphenyl)-2-(2'-thienyl)pyrrole
  参考文献：
  名称：

  Arylamino-thieno-oxobutanamides under Lawesson’s Conditions: Competition between Thienylpyrrole and Bithiophene Formation

  摘要：

  通过用 Lawesson 试剂处理芳基氨基噻吩氧代丁酰胺，合成了 1-芳基-2-噻吩基取代的吡咯和/或 5-芳基氨基-2,2′-联噻吩。这些化合物又是通过 DCC-BtOH 介导的 4-氧代-(2-噻吩基)丁酸直接酰胺化反应制备的。

  DOI：

  10.1055/s-2004-834952

文献信息

• Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties
  作者：M. Manuela M. Raposo、Ana M.R.C. Sousa、G. Kirsch、F. Ferreira、M. Belsley、E. de Matos Gomes、A. Maurício C. Fonseca

  DOI：10.1016/j.tet.2005.09.062

  日期：2005.12

  Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2'-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryi-2-(2'-thienyl)pyrroles 2 using TCNE. The tricyanovinyl-derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities beta of the mentioned compounds. The beta values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties. (c) 2005 Elsevier Ltd. All rights reserved.
• Arylamino-thieno-oxobutanamides under Lawesson’s Conditions: Competition between Thienylpyrrole and Bithiophene Formation
  作者：M. Manuela Raposo、Ana M. Sampaio、G. Kirsch

  DOI：10.1055/s-2004-834952

  日期：——

  1-Aryl-2-thienyl-substituted pyrroles and/or 5-arylamino-2,2′-bithiophenes were synthesized by treatment of arylamino-thieno-oxobutanamides with Lawesson’s reagent. These in turn were prepared by direct amidation of 4-oxo-(2-thienyl)butanoic acid through DCC-BtOH mediated reactions.

  通过用 Lawesson 试剂处理芳基氨基噻吩氧代丁酰胺，合成了 1-芳基-2-噻吩基取代的吡咯和/或 5-芳基氨基-2,2′-联噻吩。这些化合物又是通过 DCC-BtOH 介导的 4-氧代-(2-噻吩基)丁酸直接酰胺化反应制备的。