N2,N5-bis(2-aminiphenyl)-3,3'-dimethyl-4,4'-diphenyl-2,2'-bipyrrole-5,5'-dicarboxamide | 936261-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N2,N5-bis(2-aminiphenyl)-3,3'-dimethyl-4,4'-diphenyl-2,2'-bipyrrole-5,5'-dicarboxamide
• 英文别名: N-(2-aminophenyl)-5-[5-[(2-aminophenyl)carbamoyl]-3-methyl-4-phenyl-1H-pyrrol-2-yl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxamide
• CAS: 936261-67-5
• 化学式: C₃₆H₃₂N₆O₂
• 分子量: 580.689
• InChiKey: JVAVYEOCFMNTFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  142
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N2,N5-bis(2-aminiphenyl)-3,3'-dimethyl-4,4'-diphenyl-2,2'-bipyrrole-5,5'-dicarboxamide 、 3,3'-dimethyl-4,4'-diphenyl-1H,1'H-[2,2'-bipyrrole]-5,5'-dicarboxylic acid chloride 在 吡啶 、 四丁基磷酸氢铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以57%的产率得到3,18,21,36-Tetramethyl-4,17,22,35-tetraphenyl-7,14,25,32,37,38,39,40-octazaheptacyclo[32.2.1.12,5.116,19.120,23.08,13.026,31]tetraconta-1(36),2,4,8,10,12,16,18,20,22,26,28,30,34-tetradecaene-6,15,24,33-tetrone
  参考文献：
  名称：

  扩展蓝宝石：朝向选择性磷酸盐结合。

  摘要：

  描述了新型大环寡吡咯受体的阴离子模板合成和结合特性，其中吡咯环通过酰胺或亚胺键连接。通过阴离子模板化的[1+1]席夫碱缩合和酰化大环化反应完成了有效的合成。通过单晶 X 射线衍射分析分析游离受体及其与盐酸、乙酸、四丁基氯化铵和硫酸氢盐的主客体复合物。通过标准 1H NMR 和 UV/Vis 滴定技术在 [D6]DMSO/0.5% 水溶液中测定不同无机酸四丁基铵盐的稳定性常数。根据滴定数据，含有三个吡咯环（10 和 12）的受体对氟化氢、乙酸盐和磷酸二氢盐具有高亲和力（log Ka=5-7），与氯化物和硫酸氢盐相互作用较弱。具有四个吡咯环的氨基联吡咯受体 11 和 13 对磷酸二氢盐的选择性分别为 10(4)-和 10(2)-倍，这可以从乙酸四丁铵存在下的竞争滴定中推断出来。

  DOI：

  10.1002/chem.200800860
• 作为产物：
  描述：

  苯,(2-硝基-1-丙烯基)-,(E)- 在 铜 4-二甲氨基吡啶 、 sodium hydroxide 、 碘 、 碳酸氢钠 、 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 91.0h， 生成 N2,N5-bis(2-aminiphenyl)-3,3'-dimethyl-4,4'-diphenyl-2,2'-bipyrrole-5,5'-dicarboxamide
  参考文献：
  名称：

  新型氨基胺型多齿镊子配体的合成

  摘要：

  A series of new tweezers amido-amine ligands containing pyrrole, bipyrrole, and dipyrrolylmethane fragments were synthesized by reaction of 2-thioxothiazolidin-3-yl derivatives of alpha-pyrrolecarboxylic acids {5-[1(5-carboxy-3-methyl-4-phenyl-1H-pyrrol-2-yl)-methylethyl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid, 5-[(5-carboxy-3-methyl-4-phenyl-1H-pyrrol-2-yl)phenylmethyl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid, 5-(5-carboxy-3-methyl-4-phenyl-1H-pyrrol-2-yl)-4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid, and 3,4-dimethyl-pyrrole-2,5-dicarboxylic acid} with o-phenylenediamine. All compounds obtained were characterized by elemental analysis, NMR and mass spectra.

  DOI：

  10.1134/s1070428007020236

文献信息

• Bipyrrole- and Dipyrromethane-Based Amido-imine Hybrid Macrocycles. New Receptors for Oxoanions
  作者：Evgeny A. Katayev、Nikolay V. Boev、Victor N. Khrustalev、Yuri A. Ustynyuk、I. G. Tananaev、Jonathan L. Sessler

  DOI：10.1021/jo0624849

  日期：2007.4.1

  Three new amido-imine-type hybrid macrocycles based on substituted pyrrole units have been synthesized and shown to act as effective receptors for oxoanions in the solid state and in acetonitrile solution. One of the macrocycles in question, compound 15, was characterized by X-ray diffraction analysis as the free macrocycle and as a complex with sulfuric acid. A comparison of the resulting structures reveals that this receptor is capable of undergoing a conformational change and, as a consequence, varying the number of donor sites that can interact with a bound substrate. This system and the other two new receptors described in this work (macrocycles 14 and 16, respectively) display a high affinity toward oxoanions (studied as their tetrabutylammonium (TBA) salts), with association constants on the order of 10(7) M-1 being determined in acetonitrile solution using standard UV-vis spectroscopic titration methods. A competitive titration method was used to determine affinity constants in excess of ca. 10(6) M-1. Two of the receptors (14 and 15) were found to bind acetate, hydrogen sulfate, and dihydrogen phosphate anion well, and the bipyrrole-based receptor (14) was also found to bind the perrhenate anion. In contrast, the bis-dipyrromethane-derived receptor (16) was found to bind chloride anion preferentially. The unusual selectivity displayed by 16 for this spherical anion was rationalized on the basis of single-crystal X-ray diffraction data and DFT modeling calculations, which revealed a rigid structure appropriately suited for chloride anion recognition.
• Synthesis of new polydentate tweezers ligands of amido-amine type
  作者：N. V. Boev、Yu. A. Ustynyuk

  DOI：10.1134/s1070428007020236

  日期：2007.2

  A series of new tweezers amido-amine ligands containing pyrrole, bipyrrole, and dipyrrolylmethane fragments were synthesized by reaction of 2-thioxothiazolidin-3-yl derivatives of alpha-pyrrolecarboxylic acids 5-[1(5-carboxy-3-methyl-4-phenyl-1H-pyrrol-2-yl)-methylethyl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid, 5-[(5-carboxy-3-methyl-4-phenyl-1H-pyrrol-2-yl)phenylmethyl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid, 5-(5-carboxy-3-methyl-4-phenyl-1H-pyrrol-2-yl)-4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid, and 3,4-dimethyl-pyrrole-2,5-dicarboxylic acid} with o-phenylenediamine. All compounds obtained were characterized by elemental analysis, NMR and mass spectra.
• Expanding Sapphyrin: Towards Selective Phosphate Binding
  作者：Evgeny A. Katayev、Nikolay V. Boev、Ekaterina Myshkovskaya、Victor N. Khrustalev、Yu. A. Ustynyuk

  DOI：10.1002/chem.200800860

  日期：2008.10.10

  The anion-templated syntheses and binding properties of novel macrocyclic oligopyrrole receptors in which pyrrole rings are linked through amide or imine bonds are described. The efficient synthesis was accomplished by anion-templated [1+1] Schiff-base condensation and acylation macrocyclization reactions. Free receptors and their host-guest complexes with hydrochloric acid, acetic acid, tetrabutylammonium

  描述了新型大环寡吡咯受体的阴离子模板合成和结合特性，其中吡咯环通过酰胺或亚胺键连接。通过阴离子模板化的[1+1]席夫碱缩合和酰化大环化反应完成了有效的合成。通过单晶 X 射线衍射分析分析游离受体及其与盐酸、乙酸、四丁基氯化铵和硫酸氢盐的主客体复合物。通过标准 1H NMR 和 UV/Vis 滴定技术在 [D6]DMSO/0.5% 水溶液中测定不同无机酸四丁基铵盐的稳定性常数。根据滴定数据，含有三个吡咯环（10 和 12）的受体对氟化氢、乙酸盐和磷酸二氢盐具有高亲和力（log Ka=5-7），与氯化物和硫酸氢盐相互作用较弱。具有四个吡咯环的氨基联吡咯受体 11 和 13 对磷酸二氢盐的选择性分别为 10(4)-和 10(2)-倍，这可以从乙酸四丁铵存在下的竞争滴定中推断出来。