1,3,5-tris[4-benzyloxy-3-(N-(6-methyl-2-pyridyl)carbamoyl)phenyl]benzene | 484052-50-8

• 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: 1,3,5-tris[4-benzyloxy-3-(N-(6-methyl-2-pyridyl)carbamoyl)phenyl]benzene
• CAS: 484052-50-8
• 化学式: C₆₆H₅₄N₆O₆
• 分子量: 1027.19
• InChiKey: XDMZFLUNHIGIBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.29
• 重原子数：
  78.0
• 可旋转键数：
  18.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  153.66
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,3,5-tris[4-benzyloxy-3-(N-(6-methyl-2-pyridyl)carbamoyl)phenyl]benzene 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以85%的产率得到1,3,5-tris[3-(N-(6-methyl-2-pyridyl)carbamoyl-4-hydroxy)phenyl]benzene
  参考文献：
  名称：

  Dual Binding Mode of Methylmethanetriacetic Acid to Tripodal Amidopyridine Receptors

  摘要：

  A series of tripodal amidopyridine receptors capable of selective recognition of methylmethanetriacetic acid (MMTA) in organic solvents is described. Intramolecular hydrogen-bonding groups, built into some of the receptors, were designed as preorganization devices. Binding was studied by NMR titration, variable temperature NMR experiments, 2D-NMR, isothermal titration calorimetry, and single-crystal X-ray crystallography. The results reveal that a balancing act between inter- and intramolecular hydrogen-bonding interactions in the complexes governs both the dynamics and the geometry of binding. Receptor 1b (without intramolecular hydrogen-bonding groups) features a simple symmetric MMTA binding geometry with optimal enthalpic interactions. In sharp contrast, receptor 1a (with intramolecular hydrogen-bonding groups) reveals a temperature-dependent dual binding mode where MMTA can bind in two completely different geometries. The two solution binding geometries of 1a.AMTA were unraveled by NMR experiments and correlated to the X-ray structures.

  DOI：

  10.1021/jo025787l
• 作为产物：
  描述：

  1,3,5-tris(4-hydroxy-3-methoxycarbonylphenyl)benzene 在 sodium hydroxide 、 氯化亚砜 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 40.0h， 生成 1,3,5-tris[4-benzyloxy-3-(N-(6-methyl-2-pyridyl)carbamoyl)phenyl]benzene
  参考文献：
  名称：

  Dual Binding Mode of Methylmethanetriacetic Acid to Tripodal Amidopyridine Receptors

  摘要：

  A series of tripodal amidopyridine receptors capable of selective recognition of methylmethanetriacetic acid (MMTA) in organic solvents is described. Intramolecular hydrogen-bonding groups, built into some of the receptors, were designed as preorganization devices. Binding was studied by NMR titration, variable temperature NMR experiments, 2D-NMR, isothermal titration calorimetry, and single-crystal X-ray crystallography. The results reveal that a balancing act between inter- and intramolecular hydrogen-bonding interactions in the complexes governs both the dynamics and the geometry of binding. Receptor 1b (without intramolecular hydrogen-bonding groups) features a simple symmetric MMTA binding geometry with optimal enthalpic interactions. In sharp contrast, receptor 1a (with intramolecular hydrogen-bonding groups) reveals a temperature-dependent dual binding mode where MMTA can bind in two completely different geometries. The two solution binding geometries of 1a.AMTA were unraveled by NMR experiments and correlated to the X-ray structures.

  DOI：

  10.1021/jo025787l

文献信息

• Molecular recognition of cis-1,3,5-cyclohexane tricarboxylic acid
  作者：Pablo Ballester、Antoni Costa、Pere M. Deyà、José F. González、M.Carmen Rotger、Ghislain Deslongchamps

  DOI：10.1016/s0040-4039(00)73106-6

  日期：1994.5

  The design and synthesis of a new receptor designed to bind tricarboxylic acids in organic solvents is described. The properties of the complex formed between the new receptor and cis-1,3,5-cyclohexanetricarboxylic acid are studied.