1-phenyl-2-(2'-thienyl)pyrrole | 849403-49-2

• 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-(2'-thienyl)pyrrole
• 英文别名: 1-phenyl-2-thienyl-pyrrole；1-Phenyl-2-thiophen-2-ylpyrrole
• CAS: 849403-49-2
• 化学式: C₁₄H₁₁NS
• 分子量: 225.314
• InChiKey: ZYTPIGLFCUMUND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-phenyl-6-thienyl-3,6-dihydro-2H-[1,2]oxazine 在 copper nanoparticles on activated carbon 作用下， 反应 6.0h， 以88%的产率得到1-phenyl-2-(2'-thienyl)pyrrole
  参考文献：
  名称：

  3,6-二氢-1,2-恶嗪合成铜催化的吡咯

  摘要：

  可以在纯净的加热条件下，使用非均相的碳载铜（Cu / C），从3,6-二氢-1,2-恶嗪有效地合成高度官能化的吡咯。此外，原位形成的3,6-二氢-1,2-恶嗪经由亚硝基的亲二烯体和1,3-二烯和以下的Cu / C催化的吡咯合成还提供了相应的吡咯衍生物之间的杂Diels-Alder反应以一锅的方式。

  DOI：

  10.1039/c8gc01373j

文献信息

• Modification of organic compounds with Lawesson’s reagent
  作者：L. A. Kayukova、K. D. Praliyev、V. G. Gut’yar、G. P. Baitursynova

  DOI：10.1134/s1070428015020025

  日期：2015.2

  Application in organic synthesis of Lawesson’s reagent, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, provides a possibility to replace an oxygen atom for a sulfur atom in the carbonyl group of ketones, esters, amides, in ether group, and also either to induce a rearrangement of the initial structure of organic compounds with or without inclusion of sulfur atoms or to lead to

  Lawesson试剂2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二膦环-2,4-二硫化物在有机合成中的应用为羰基中的硫原子取代氧原子提供了可能性在醚基团中的一组酮，酯，酰胺，还可以诱导含有或不含有硫原子的有机化合物的初始结构重排，或导致形成各种类型的有机磷化合物。形成的有机硫化合物表现出广泛的生物学作用。
• 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。
• Synthesis of Pyrrole via Formal Cycloaddition of Allyl Ketone and Amine under Metal-Free Conditions
  作者：Jinli Wang、Meizhong Tang、Weijin Gu、Shenlin Huang、Lan-Gui Xie

  DOI：10.1021/acs.joc.2c01565

  日期：2022.9.16

  A new metal-free synthesis of pyrrole from allyl ketone and amine has been established. The reaction proceeds via an thiolative activation of the C–C double bond with dimethyl(methylthio)sulfonium trifluoromethanesulfonate, followed by a nucleophilic ring-opening addition of primary amine to the generated episulfonium intermediate, and then an internal condensation and aromatization. This mild procedure

  建立了一种由烯丙基酮和胺无金属合成吡咯的新方法。该反应通过用二甲基（甲硫基）锍三氟甲磺酸盐对 C-C 双键进行硫醇化活化，然后将伯胺与生成的环鎓中间体进行亲核开环加成，然后进行内部缩合和芳构化。这种温和的过程为通过正式的 [4 + 1] 环加成反应构建取代的吡咯提供了一种新的策略。
• 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.
• Thienylpyrrole azo dyes: synthesis, solvatochromic and electrochemical properties
  作者：M. Manuela M. Raposo、Ana M.R.C. Sousa、A. Maurício C. Fonseca、G. Kirsch

  DOI：10.1016/j.tet.2005.06.039

  日期：2005.8

  The synthesis and the evaluation of solvatochromic and electrochemical properties of new donor-acceptor-substituted thienylpyrrole, azo dyes 3 are described. These derivatives exhibit dramatic changes in both their electronic and redox properties in comparison with thienylpyrroles 1. In agreement with the solvatochromic and electrochemical studies of push-pull derivatives 3 the new compounds prepared, may find application in the manufacture of new materials with notable non-linear optical properties. (c) 2005 Elsevier Ltd. All rights reserved.