1,3,5-tris[3-(N-6-methyl-2-pyridyl)carbamoyl-5-propylphenyl]benzene | 221021-04-1

• 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[3-(N-6-methyl-2-pyridyl)carbamoyl-5-propylphenyl]benzene
• 英文别名: 3-[3,5-bis[3-[C-hydroxy-N-(6-methylpyridin-2-yl)carbonimidoyl]-5-propylphenyl]phenyl]-N-(6-methylpyridin-2-yl)-5-propylbenzenecarboximidic acid
• CAS: 221021-04-1
• 化学式: C₅₄H₅₄N₆O₃
• 分子量: 835.061
• InChiKey: OEUAYZTXGDNWMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  63
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Cis-1,3,5-Cyclohexanetricarboxylic Acid 、 1,3,5-tris[3-(N-6-methyl-2-pyridyl)carbamoyl-5-propylphenyl]benzene 以 甲醇 、 氯仿 为溶剂， 生成
  参考文献：
  名称：

  远程分子内氢键对顺式1,3,5-环己烷三基丁酸分子识别的热力学的影响

  摘要：

  利用可变温度结合研究和等温滴定微量热法，探讨了三脚架宿主对顺式-1,3,5-环己烷三丁酸酯酸的分子识别的热力学。远程分子内氢键（用于构象地限制主体之一）对结合过程ΔH和ΔS的热力学功能表现出很大的影响，而对ΔG的影响很小。这表明由分子内氢键施加的构象锁将受体组织为对于三酸的结合而言不是最佳的构象。

  DOI：

  10.1016/s0040-4039(98)80050-6
• 作为产物：
  描述：

  水杨酸甲酯 在 10percent Pd/C 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 甲酸 、 氯化亚砜 、 PPA 、 四氯化硅 、 氢气 、 caesium carbonate 、 N,N-二甲基苯胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0~110.0 ℃ 、62.05 kPa 条件下， 反应 133.0h， 生成 1,3,5-tris[3-(N-6-methyl-2-pyridyl)carbamoyl-5-propylphenyl]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

• Selective Binding of <i>cis</i>-1,3,5-Cyclohexane Tricarboxylic Acid vs Its Epimeric <i>trans </i>Isomer by a Tripodal Amidopyridine Receptor; Crystal Structures of the 1:1 Complexes
  作者：Pablo Ballester、Magdalena Capó、Antoni Costa、Pere M. Deyà、Rosa Gomila、Andreas Decken、Ghislain Deslongchamps

  DOI：10.1021/ol0069148

  日期：2001.1.1

  [GRAPHICS]A tripodal tris-amidopyridine receptor forms a 1:1 complex with trans-1,3,5-cyclohexane tricarboxylic acid that is 1 order of magnitude less stable than the one formed with the corresponding cis-triacid epimer, The X-ray crystal structures of the complexes have been determined, confirming the binding geometry derived from NMR data in solution and force field calculations, and its geometrical features are used to explain the observed selectivity.