N-(2-aminophenyl)-5-[2-[5-[(2-aminophenyl)carbamoyl]-3-methyl-4-phenyl-1H-pyrrol-2-yl]propan-2-yl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxamide | 936261-68-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: N-(2-aminophenyl)-5-[2-[5-[(2-aminophenyl)carbamoyl]-3-methyl-4-phenyl-1H-pyrrol-2-yl]propan-2-yl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxamide
• CAS: 936261-68-6
• 化学式: C₃₉H₃₈N₆O₂
• 分子量: 622.77
• InChiKey: RHIWUFJVPIAJRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  47
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  2,2'-(5-formyl-3-methyl-4-propylpyrrolyl)(p-tolyl)methane 、 N-(2-aminophenyl)-5-[2-[5-[(2-aminophenyl)carbamoyl]-3-methyl-4-phenyl-1H-pyrrol-2-yl]propan-2-yl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxamide 在 硫酸 作用下， 以 甲醇 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Bipyrrole- and Dipyrromethane-Based Amido-imine Hybrid Macrocycles. New Receptors for Oxoanions

  摘要：

  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.

  DOI：

  10.1021/jo0624849
• 作为产物：
  描述：

  苯,(2-硝基-1-丙烯基)-,(E)- 在 sodium hydroxide 、 甲烷磺酸 、 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 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 80.0h， 生成 N-(2-aminophenyl)-5-[2-[5-[(2-aminophenyl)carbamoyl]-3-methyl-4-phenyl-1H-pyrrol-2-yl]propan-2-yl]-4-methyl-3-phenyl-1H-pyrrole-2-carboxamide
  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

• 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.
• 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.