1-phenyl-2-(5'-formyl-2'-thienyl)pyrrole | 887830-26-4

• 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-phenyl-2-(5'-formyl-2'-thienyl)pyrrole
• 英文别名: 5-(1-Phenylpyrrol-2-yl)thiophene-2-carbaldehyde
• CAS: 887830-26-4
• 化学式: C₁₅H₁₁NOS
• 分子量: 253.324
• InChiKey: ORQQZGVOQWSGOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(5'-formyl-2'-thienyl)pyrrole 、 2-氨基苯硫醇 以 二甲基亚砜 为溶剂， 以48%的产率得到2-(1''-phenyl-2''-(thien-2'-yl)pyrrolyl)-1,3-benzothiazole
  参考文献：
  名称：

  Synthesis and characterization of new thienylpyrrolyl-benzothiazoles as efficient and thermally stable nonlinear optical chromophores

  摘要：

  The synthesis and full characterization of new chromophores with second-order nonlinearities containing thienylpyrrolyl and benzothiazolyl moieties are reported. The solvatochromic behavior of the compounds was investigated. The hyperpolarizabilities beta of derivatives 4-6 were measured using hyper-Rayleigh scattering and thermogravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that strong nonlinearity is balanced by good thermal stability especially for chromophores 6b and 6c, making them good candidates for NLO applications. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.065
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 1-phenyl-2-(2'-thienyl)pyrrole 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以78%的产率得到1-phenyl-2-(5'-formyl-2'-thienyl)pyrrole
  参考文献：
  名称：

  Synthesis of formyl-thienylpyrroles: versatile building blocks for NLO materials

  摘要：

  Several formyl-substituted 1-alkyl(aryl)-2-(2'-thienyl)pyrroles 3-7 were synthesized by functionalization of the pyrrole or thiophene ring of thienylpyrroles 2 using different methods: Vilsnicier formylation or metalation followed by reaction with DMF. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.004

文献信息

• Metal-Free Photocatalyzed Cross Coupling of Bromoheteroarenes with Pyrroles
  作者：Leyre Marzo、Indrajit Ghosh、Francisco Esteban、Burkhard König

  DOI：10.1021/acscatal.6b01452

  日期：2016.10.7

  successively trapped by pyrroles for the synthesis of heteroaromatic biaryls in moderate to excellent yields. The synthetically important photoredox catalytic C–H heteroarylation reaction works for a broad range of brominated electron-rich heteroarenes and chlorinated heteroarenes bearing electron withdrawing groups. In addition, this methodology was applied to the formal synthesis of a benzimidazole derivative

  罗丹明6G的激发自由基阴离子可还原杂芳基溴化物和氯化物，生成杂芳基自由基，随后这些杂芳基自由基被吡咯捕获，以中等至极好的收率合成杂芳族联芳基。具有重要合成意义的光氧化还原催化CH–H杂芳基化反应可用于各种带电子吸取基团的溴化富电子杂芳烃和氯化杂芳烃。另外，该方法学被用于具有有趣药理特性的苯并咪唑衍生物II的正式合成。
• Synthesis and Characterization of Dicyanovinyl-Substituted Thienylpyrroles as New Nonlinear Optical Chromophores
  作者：M. Manuela M. Raposo、Ana M. R. C. Sousa、G. Kirsch、P. Cardoso、M. Belsley、E. de Matos Gomes、A. Maurício C. Fonseca

  DOI：10.1021/ol061277s

  日期：2006.8.1

  New dicyanovinyl-substituted 1-(alkyl)aryl-2-(2'-thienyl) pyrroles 2 were synthesized and characterized. The solvatochromic behavior of the synthesized compounds was investigated. All the derivatives showed reversible oxidation and reduction on the CV time scale. The hyperpolarizabilities (beta) of compounds 2 were measured using hyper-Rayleigh scattering. The results are among the highest beta values reported for donor-acceptor-substituted thienylpyrroles.
• Synthesis of formyl-thienylpyrroles: versatile building blocks for NLO materials
  作者：M. Manuela M. Raposo、Ana M.R.C. Sousa、A. Maurício C. Fonseca、G. Kirsch

  DOI：10.1016/j.tet.2006.02.004

  日期：2006.4

  Several formyl-substituted 1-alkyl(aryl)-2-(2'-thienyl)pyrroles 3-7 were synthesized by functionalization of the pyrrole or thiophene ring of thienylpyrroles 2 using different methods: Vilsnicier formylation or metalation followed by reaction with DMF. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and characterization of new thienylpyrrolyl-benzothiazoles as efficient and thermally stable nonlinear optical chromophores
  作者：Rosa M.F. Batista、Susana P.G. Costa、Elisabeth L. Malheiro、Michael Belsley、M. Manuela M. Raposo

  DOI：10.1016/j.tet.2007.03.065

  日期：2007.5

  The synthesis and full characterization of new chromophores with second-order nonlinearities containing thienylpyrrolyl and benzothiazolyl moieties are reported. The solvatochromic behavior of the compounds was investigated. The hyperpolarizabilities beta of derivatives 4-6 were measured using hyper-Rayleigh scattering and thermogravimetric analysis (TGA) was used to evaluate their thermal stability. The experimental results indicate that strong nonlinearity is balanced by good thermal stability especially for chromophores 6b and 6c, making them good candidates for NLO applications. (C) 2007 Elsevier Ltd. All rights reserved.