1-propyl-2-(5'-formyl-2'-thienyl)pyrrole | 887830-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 1-propyl-2-(5'-formyl-2'-thienyl)pyrrole
• 英文别名: 5-(1-Propylpyrrol-2-yl)thiophene-2-carbaldehyde；5-(1-propylpyrrol-2-yl)thiophene-2-carbaldehyde
• CAS: 887830-25-3
• 化学式: C₁₂H₁₃NOS
• 分子量: 219.307
• InChiKey: QSKVJCLMXDCURZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-propyl-2-(5'-formyl-2'-thienyl)pyrrole 、 2-氨基苯硫醇 以 二甲基亚砜 为溶剂， 以36%的产率得到2-(1''-propyl-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：

  3-(2-噻吩甲酰基)丙酸 在 劳森试剂 、 正丁基锂 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 1-propyl-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

• 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.