N-(4-fluorophenyl)-2,5-diphenylpyrrole | 1456622-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(4-fluorophenyl)-2,5-diphenylpyrrole
• 英文别名: 1-(4-fluorophenyl)-2,5-diphenyl-1H-pyrrole；1-(4-Fluorophenyl)-2,5-diphenylpyrrole
• CAS: 1456622-49-3
• 化学式: C₂₂H₁₆FN
• 分子量: 313.374
• InChiKey: JPSXRHXRBSJIJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-fluorophenyl)-2,5-diphenylpyrrole 在 iron(III) chloride 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 以50%的产率得到1,1'-bis(4-fluorophenyl)-2,2',5,5'-tetraphenyl-3,3'-bipyrrole
  参考文献：
  名称：

  通过 1,2,5-三取代吡咯的氧化均偶联合成 3,3'-双吡咯的直接方法

  摘要：

  开发了一种在 FeCl3 存在下，在混合溶剂中，通过 1,2,5-三取代吡咯的氧化 C-H 均偶联有效和直接合成 3,3'-联吡咯的方法。

  DOI：

  10.1246/cl.130253
• 作为产物：
  描述：

  1，4-二苯基丁二炔 、 4-氟苯胺 在 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以70%的产率得到N-(4-fluorophenyl)-2,5-diphenylpyrrole
  参考文献：
  名称：

  Synthesis, characterization and semiconducting behavior of N,2,5-trisubstituted pyrroles

  摘要：

  In this work, N,2,5-trisubstituted pyrroles were synthesized and characterized by IR, UV-Vis and NMR spectroscopies. These materials' electronic and optical properties were then evaluated. Theoretical calculations were carried out by means of the Gaussian09 software and all the involved species were geometrically optimized in order to obtain the theoretic HOMO, LUMO and band gaps. From the HOMO and LUMO calculations, it turns out that monomer 1-(3,5-dinitrophenyl)-2,5-diphenyl-1H-pyrrole could be used as a p-type semiconductor or n-type semiconductor, depending on the substituent. The experimental optical band gaps were obtained by the Tauc and Cody methods and compared to the ones calculated through OFT. The results show that the semiconducting behavior is found in all the monomers and depends on the functional group of the structure, its crystallinity degree, as well as its HOMO and its LUMO energies. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2018.05.086

文献信息

• s-Block-Metal-Mediated Hydroamination of Diphenylbutadiyne with Primary Arylamines Using a Dipotassium Tetrakis(amino)calciate Precatalyst
  作者：Fadi M. Younis、Sven Krieck、Helmar Görls、Matthias Westerhausen

  DOI：10.1021/acs.organomet.5b00449

  日期：2015.7.27

  The hydroamination of diphenylbutadiyne with primary arylamines requires a reactive catalyst. In the presence of heterobimetallic K-2[CaN(H)Dipp}(4)] (Dipp = 2,6-diisopropylphenyl) the performance of this reaction in THF yields 2-tert-butyl-6,7,10,11-tetraphenyl-9H-cyclohepta[c]quinoline (1a) and 2-fluoro-6,7,10,11-tetraphenyl-9H-cyclohepta[c]quinoline (1b) within 3 days at room temperature when 4-tert-butyl- and 4-fluoroaniline, respectively, have been used. During this catalysis o-CH activation occurs and quinoline derivatives are formed. Blocking the o-CH positions by methyl groups and use of 2,4,6-trimethylaniline under similar reaction conditions leads to the formation of N-mesityl-7-(E)-((mesitylimino)(phenyl)methyl)-2,3,6-triphenylcyclohepta-1,3,6-trienylamine (2) containing a beta-diketimine unit with a N-H.....N hydrogen bridge. NMR experiments with labeled 4-tert-butylaniline verify the transfer of N-bound hydrogen atoms to the newly formed cycloheptatriene ring. If the s-block-metal-mediated hydroamination of diphenylbutadiyne is performed in refluxing THF for 6 days, N-aryl-2,5-diphenylpyrroles 3a-d (3a, R = tBu, R' = H; 3b, R = F, R' = H; 3c, R = R' = Me; 3d, R = R' = H) are obtained regardless of the substitution pattern of the arylamines.