3,4-diphenylpyrrole-2,5-dicarboxylic acid chloride | 365214-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3,4-diphenylpyrrole-2,5-dicarboxylic acid chloride
• 英文别名: 3,4-diphenyl-1H-pyrrole-2,5-dicarbonyl dichloride；3,4-diphenylpyrrole-2,5-dicarbonyl dichloride；1H-Pyrrole-2,5-dicarbonyl dichloride, 3,4-diphenyl-；3,4-diphenyl-1H-pyrrole-2,5-dicarbonyl chloride
• CAS: 365214-51-3
• 化学式: C₁₈H₁₁Cl₂NO₂
• 分子量: 344.197
• InChiKey: SPIGQLTZUOLMIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  534.9±50.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-diphenylpyrrole-2,5-dicarboxylic acid chloride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3,4-diphenyl-1H-pyrrole-2,5-dicarboxylic acid bis-[(2-acetylamino-ethyl)-amide]
  参考文献：
  名称：

  Pendant arm pyrrolic amide cleft anion receptors

  摘要：

  已对胺、铵和酰胺侧臂2,5-二氨基吡咯衍生物作为阴离子受体的倾向进行了研究；通过1H NMR滴定技术确定了这些物质的阴离子配位能力，结果表明胺官能化受体对硫酸氢阴离子具有显著的选择性。

  DOI：

  10.1039/b204295a
• 作为产物：
  描述：

  3,4-diphenyl-1H-pyrrole-2,5-dicarboxylic acid 在 氯化亚砜 作用下， 生成 3,4-diphenylpyrrole-2,5-dicarboxylic acid chloride
  参考文献：
  名称：

  Amidopyrroles: from anion receptors to membrane transport agents

  摘要：

  酰胺吡咯已被用于多种阴离子受体和传感器。 2,5-双酰胺吡咯在有机溶液中表现出选择性含氧阴离子络合特性，而含有二吡咯甲烷基团的双酰胺在 DMSO-d6 和水的混合物中与磷酸二氢阴离子形成强络合物。 2,5-双酰胺基吡咯单元的去质子化可以产生有趣的固态结构，包括形成正交氢键二聚体。酰胺吡咯基团也已用于离子对受体和 HCl 膜转运剂中。

  DOI：

  10.1039/b504596g

文献信息

• Anion complexation and electrochemical behaviour of ferrocene-appended amido-pyrrole cleftsElectronic supplementary information (ESI) available: 1H and 13C NMR spectra of 1 and 2, 1H NMR titrations of 1 and 2 with various putative anionic guests and with chloride following ferrocene CH resonances. See http://www.rsc.org/suppdata/nj/b2/b202989h/
  作者：Guy Denuault、Philip A. Gale、Michael B. Hursthouse、Mark E. Light、Colin N. Warriner

  DOI：10.1039/b202989h

  日期：2002.6.24

  Two amido-pyrrole cleft anion receptors bearing two ferrocene reporter groups have been synthesised and crystallographically characterised; the receptors contain either a non-conjugated or conjugated link between the anion-binding amido-pyrrole unit and the ferrocene reporter groups. The anion binding affinities and electrochemical behaviour of the receptors in the absence and presence of anions have been studied by 1H NMR titration techniques and cyclic voltammetry using a Pt microdisc working electrode, respectively.

  已合成并表征了带有两个二茂铁报道基团的两种酰胺-吡咯裂隙阴离子受体；受体在阴离子结合酰胺基吡咯单元和二茂铁报告基团之间包含非共轭或共轭连接。分别通过 1 H NMR 滴定技术和使用 Pt 微盘工作电极的循环伏安法研究了在不存在和存在阴离子的情况下受体的阴离子结合亲和力和电化学行为。
• Nitrophenyl derivatives of pyrrole 2,5-diamides: structural behaviour, anion binding and colour change signalled deprotonationElectronic supplementary information (ESI) available: 1H NMR, 13C NMR and mass spectra for compounds 2 and 3, NMR anion titration profiles in DMSO-d6–0.5% water. See http://www.rsc.org/suppdata/ob/b2/b210848h/
  作者：Salvatore Camiolo、Philip A. Gale、Michael B. Hursthouse、Mark E. Light

  DOI：10.1039/b210848h

  日期：2003.2.11

  Two new pyrrole 2,5-diamide clefts have been synthesized containing 4-nitrophenyl or 3,5-dinitrophenyl groups appended to the amide positions. The 3,5-dinitrophenyl derivative has been shown to deprotonate in the presence of fluoride, which in acetonitrile solution, gives rise to a deep blue colour.

  已经合成了两个新的吡咯2，5-二酰胺裂口，其含有附在酰胺位置上的4-硝基苯基或3，5-二硝基苯基。3,5-二硝基苯基衍生物已显示在氟化物存在下会去质子化，在乙腈溶液中会产生深蓝色。
• Diphenylpyrrole‐Strapped Calix[4]pyrrole Extractant for the Fluoride and Chloride Anions
  作者：Nam Jung Heo、Vincent M. Lynch、Dustin E. Gross、Jonathan L. Sessler、Sung Kuk Kim

  DOI：10.1002/chem.202302410

  日期：2023.11.16

  Extractants: The diphenylpyrrole-strapped calix[4]pyrrole and its dual host systems involving crown ethers enable the extraction of various fluoride and chloride salts from water.

  萃取剂：二苯基吡咯带的杯[4]吡咯及其涉及冠醚的双主体系统能够从水中萃取各种氟化物和氯化物盐。
• Mono- and bis-ferrocene 2,5-diamidopyrrole clefts: solid-state assembly, anion binding and electrochemical properties
  作者：Simon J Coles、Guy Denuault、Philip A Gale、Peter N Horton、Michael B Hursthouse、Mark E Light、Colin N Warriner

  DOI：10.1016/s0277-5387(02)01401-8

  日期：2003.3

  Four amido-pyrrole cleft anion receptors bearing one or two ferrocene reporter groups have been synthesised and crystallographically characterised. The receptors contain either a non-conjugated (1 and 3) or conjugated (2 and 4) link between the anion binding amido-pyrrole unit and the ferrocene reporter groups. The anion binding affinities and electrochemical behaviour of the receptors in the absence and presence of anions have been studied by H-1 NMR titration techniques and cyclic voltammetry using a Pt microdisc working electrode, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A dual host approach to NiSO₄ extraction
  作者：Gareth W. Bates、James E. Davidson、Ross S. Forgan、Philip A. Gale、David K. Henderson、Michael G. King、Mark E. Light、Stephen J. Moore、Peter A. Tasker、Christine C. Tong

  DOI：10.1080/10610278.2011.631706

  日期：2012.2.1

  This paper reports the synthesis of sulphate extractants, N,N'-bis-(2-dibutylamino-ethyl)-isophthalamide (1), pyridine-2,6-dicarboxylic acid bis-[(2-dibutylamino-ethyl)-amide] (2) and 3,4-diphenyl-1H-pyrrole-2,5-dicarboxylic acid bis-[(2-dibutylamino-ethyl)-amide] (3), and demonstrates that, in combination with a commercially available oxime extractant 2-hydroxy-5-nonyl benzaldehyde oxime (P50), these dual host systems are better extractants for nickel(II) sulphate than the metal salt extractant, 5-nonyl-3-dihexylaminomethyl-2-hydroxy-benzaldehyde oxime (4).