1-(4-methoxybenzyl)-2-[3-(2-trimethylsilanylethoxycarbonylamino)phenyl]-1H-imidazole-4-carboxylic acid 4-methoxybenzyl ester | 601494-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methoxybenzyl)-2-[3-(2-trimethylsilanylethoxycarbonylamino)phenyl]-1H-imidazole-4-carboxylic acid 4-methoxybenzyl ester
• CAS: 601494-35-3
• 化学式: C₃₂H₃₇N₃O₆Si
• 分子量: 587.748
• InChiKey: ZAUBOJSPXFFTQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  100.91
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyl)-2-[3-(2-trimethylsilanylethoxycarbonylamino)phenyl]-1H-imidazole-4-carboxylic acid 4-methoxybenzyl ester 在 lithium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  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：

  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