N-{4-[1-(4-Amino-3,5-dimethyl-phenyl)-cyclohexyl]-2,6-dimethyl-phenyl}-4-tert-butyl-benzamide | 299173-86-7

• 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: N-{4-[1-(4-Amino-3,5-dimethyl-phenyl)-cyclohexyl]-2,6-dimethyl-phenyl}-4-tert-butyl-benzamide
• 英文别名: N-[4-[1-(4-amino-3,5-dimethylphenyl)cyclohexyl]-2,6-dimethylphenyl]-4-tert-butylbenzamide
• CAS: 299173-86-7
• 化学式: C₃₃H₄₂N₂O
• 分子量: 482.709
• InChiKey: ZUXFWBPPZGHKQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  555.5±50.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 N-{4-[1-(4-Amino-3,5-dimethyl-phenyl)-cyclohexyl]-2,6-dimethyl-phenyl}-4-tert-butyl-benzamide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以58%的产率得到4-tert-butyl-N-[4-[1-[3,5-dimethyl-4-[(4-nitrobenzoyl)amino]phenyl]cyclohexyl]-2,6-dimethylphenyl]benzamide
  参考文献：
  名称：

  取代基对边到边的芳香相互作用的影响。

  摘要：

  化学双突变体循环已被用于测量氢键结合的拉链复合物中的边对面芳族相互作用的量，其是两个芳族环上取代基的函数。相互作用能根据取代基的组合而变化，从+1.0 kJ mol-1（排斥）到-4.9 kJ mol-1（有吸引力）。结果与哈米特取代基常数相关，这表明静电相互作用是观察到的相互作用能差异的原因。可以基于边缘环上的质子与面环上的pi电子密度之间的局部静电相互作用，以及两个芳族基团上的整体偶极子之间的整体静电相互作用，使实验合理化。

  DOI：

  10.1002/1521-3765(20020703)8:13<2847::aid-chem2847>3.0.co;2-m
• 作为产物：
  描述：

  4-[1-(4-氨基-3,5-二甲基苯基)环己基]-2,6-二甲基苯胺 、 对叔丁基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到N-{4-[1-(4-Amino-3,5-dimethyl-phenyl)-cyclohexyl]-2,6-dimethyl-phenyl}-4-tert-butyl-benzamide
  参考文献：
  名称：

  Synthesis and Recognition Properties of Aromatic Amide Oligomers:  Molecular Zippers

  摘要：

  A series of amide oligomers have been prepared from isophthalic acid and a bisaniline derivative. These compounds assemble into double-stranded zipper complexes in solution via hydrogen-bonding and edge-to-face aromatic interactions. The stability and structures of the complexes have been determined by H-1 NMR spectroscopy in chloroform solution. The stability of the complexes increases with increasing chain length, indicating cooperativity between the individual recognition sites in the oligomers. Oligomers which are complementary form more stable complexes than non-complementary systems with overhanging ends. Addition of polar solvents such as methanol destabilizes the complexes, because it competes for hydrogen-bonding interactions which appear to be the main driving force for binding in this system.

  DOI：

  10.1021/ja0012671

文献信息

• Quantitative Measurements of Edge‐to‐Face Aromatic Interactions by Using Chemical Double‐Mutant Cycles
  作者：Fiona J. Carver、Christopher A. Hunter、Philip S. Jones、David J. Livingstone、James F. McCabe、Eileen M. Seward、Pascale Tiger、Sharon E. Spey

  DOI：10.1002/1521-3765(20011119)7:22<4854::aid-chem4854>3.0.co;2-#

  日期：2001.11.19

  Synthetic H-bonded zipper complexes have been used to quantify the magnitude of an edge-to-face aromatic interaction between a benzoyl group and an aniline ring. Four chemical double-mutant cycles were constructed by using a matrix of nine closely related complexes in which the aromatic rings were sequentially substituted for alkyl substituents. The stability constants and three-dimensional structures of the complexes were determined by using 1H NMR titrations in deuterochloroform at room temperature. The value of the interaction energy is similar in all cases, the average is -1.4 +/- 0.5 kJ mol(-1). The scope and limitations of the double-mutant approach are explored, and the consequences of conformational equilibria are discussed.