5-formyl-1-(4''-methoxyphenyl)-2-(2'-thienyl)pyrrole | 887830-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-formyl-1-(4''-methoxyphenyl)-2-(2'-thienyl)pyrrole
• 英文别名: 1-(4-Methoxyphenyl)-5-thiophen-2-ylpyrrole-2-carbaldehyde；1-(4-methoxyphenyl)-5-thiophen-2-ylpyrrole-2-carbaldehyde
• CAS: 887830-21-9
• 化学式: C₁₆H₁₃NO₂S
• 分子量: 283.351
• InChiKey: BWXRKVXZCOQTJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-formyl-1-(4''-methoxyphenyl)-2-(2'-thienyl)pyrrole 、 2-氨基苯硫醇 以 二甲基亚砜 为溶剂， 以35%的产率得到2-(1'-(4'''-methoxyphenyl)-5'-(thien-2''-yl)pyrrol-2'-yl)-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-(4''-methoxyphenyl)-2-(2'-thienyl)pyrrole 在 三氯氧磷 作用下， 以12%的产率得到5-formyl-1-(4''-methoxyphenyl)-2-(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 second-order nonlinear optical properties of new chromophores containing benzimidazole, thiophene, and pyrrole heterocycles
  作者：Rosa M.F. Batista、Susana P.G. Costa、M. Belsley、M. Manuela M. Raposo

  DOI：10.1016/j.tet.2007.06.098

  日期：2007.9

  A new series of thermally stable benzimidazole-based nonlinear optical (NLO) chromophores 4 and 5 have been developed. These chromophores possess a thienylpyrrolyl π-conjugated system attached to functionalized benzimidazole heterocycles. This feature leads to robust chromophores with excellent solvatochromic properties, high thermal stabilities and good molecular optical nonlinearities.

  已经开发了一系列新的热稳定的基于苯并咪唑的非线性光学（NLO）发色团4和5。这些生色团具有与官能化的苯并咪唑杂环相连的噻吩基吡咯基π共轭体系。该特征导致具有强溶剂变色性质，高热稳定性和良好的分子光学非线性的坚固的发色团。
• 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.