2-(3-nitrophenyl)-1H-imidazole-4-carboxylic acid | 601494-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-nitrophenyl)-1H-imidazole-4-carboxylic acid
• 英文别名: 2-(3-nitrophenyl)-1H-imidazole-5-carboxylic acid
• CAS: 601494-32-0
• 化学式: C₁₀H₇N₃O₄
• mdl: MFCD14583645
• 分子量: 233.183
• InChiKey: INJFFHQKNQTVIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)-1H-imidazole-4-carboxylic acid 在 铁粉 、 sodium hydride 、 氯化铵 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(4-methoxybenzyl)-2-[3-(2-trimethylsilanylethoxycarbonylamino)phenyl]-1H-imidazole-4-carboxylic acid 4-methoxybenzyl ester
  参考文献：
  名称：

  Rigid Macrocyclic Triamides as Anion Receptors:  Anion-Dependent Binding Stoichiometries and ¹H Chemical Shift Changes

  摘要：

  The cyclic triamide of 3'-amino-3-biphenylcarboxlic acid is readily synthesized in a stepwise manner and represents a novel class of anion receptors with a large central cavity. This macrocycle binds more strongly to tetrahedral anions than spherical or planar anions in organic solvents. The binding stoichiometries for anions with symmetrical charge distribution depend on the solvent polarity, while tetrahedral p-tosylate binds to the macrocycle with 1:1 stoichiometry in all solvents studied. The H-1 NMR chemical shift changes of the protons lining the interior of the macrocycle's central cavity also depend on the geometry of the bound anion. The importance of the convergent array of hydrogen bond donors for anion binding by the macrocycle was confirmed by control studies with an acyclic triamide and a macrocycle with intramolecular hydrogen bonds.

  DOI：

  10.1021/ja034563x
• 作为产物：
  描述：

  间硝基苯甲醛 在 乙醇 、 水 、 sodium acetate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.5h， 生成 2-(3-nitrophenyl)-1H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  Discovery of novel 2-aryl-4-bis-amide imidazoles (ABAI) as anti-inflammatory agents for the treatment of inflammatory bowel diseases (IBD)

  摘要：

  DOI：

  10.1016/j.bioorg.2022.105619

文献信息

• Pyman; Stanley, Journal of the Chemical Society, 1924, vol. 125, p. 2487
  作者：Pyman、Stanley

  DOI：——

  日期：——
• Discovery of novel 2-aryl-4-bis-amide imidazoles (ABAI) as anti-inflammatory agents for the treatment of inflammatory bowel diseases (IBD)
  作者：Ling Li、Sijie Yuan、Lin Lin、Fang Yang、Ting Liu、Chenglong Xu、Huiting Zhao、Jingxuan Chen、Peihua Kuang、Ting Chen、Wenzhen Liao、Jianjun Chen

  DOI：10.1016/j.bioorg.2022.105619

  日期：2022.3
• Rigid Macrocyclic Triamides as Anion Receptors:  Anion-Dependent Binding Stoichiometries and ¹H Chemical Shift Changes
  作者：Kihang Choi、Andrew D. Hamilton

  DOI：10.1021/ja034563x

  日期：2003.8.1

  The cyclic triamide of 3'-amino-3-biphenylcarboxlic acid is readily synthesized in a stepwise manner and represents a novel class of anion receptors with a large central cavity. This macrocycle binds more strongly to tetrahedral anions than spherical or planar anions in organic solvents. The binding stoichiometries for anions with symmetrical charge distribution depend on the solvent polarity, while tetrahedral p-tosylate binds to the macrocycle with 1:1 stoichiometry in all solvents studied. The H-1 NMR chemical shift changes of the protons lining the interior of the macrocycle's central cavity also depend on the geometry of the bound anion. The importance of the convergent array of hydrogen bond donors for anion binding by the macrocycle was confirmed by control studies with an acyclic triamide and a macrocycle with intramolecular hydrogen bonds.