3,5-双(5-溴戊氧基)苯甲酸乙酯 | 142763-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-双(5-溴戊氧基)苯甲酸乙酯
• 英文名称: ethyl 3,5-bis((5-bromopentyl)oxy)benzoate
• 英文别名: Ethyl 3,5-bis[(5-bromopentyl)oxy]benzoate；ethyl 3,5-bis(5-bromopentoxy)benzoate
• CAS: 142763-07-3
• 化学式: C₁₉H₂₈Br₂O₄
• 分子量: 480.237
• InChiKey: CESKRHVNYFFNLP-UHFFFAOYSA-N

物化性质

• 沸点：
  531.5±50.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-双(5-溴戊氧基)苯甲酸乙酯 在 sodium hydroxide 、 氯化亚砜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.5h， 生成 2,8,14,20-Tetraoxatricyclo[19.3.1.19,13]hexacosa-1(25),9(26),10,12,21,23-hexaene-11,23-dicarbonyl chloride
  参考文献：
  名称：

  Recognition of axial ligands by a zinc porphyrin host on the basis of nonpolar interligand interaction

  摘要：

  A porphyrin host with a preorganized cavity on each face has been synthesized and characterized. The constants for association of the zinc complex of the porphyrin with various amine ligands were determined and compared with those of [meso-tetrakis(p-methylphenyl)porphyrinato]zinc(II) and of a "picket-fence" porphyrin zinc(II) complex. The selectivity for the amine ligands was not observed for the picket-fence porphyrin complex. Contrary to this, small secondary amines, such as azetidine, pyrrolidine, and diethylamine, that fit the shape of the cavity of the synthesized host complex bind more strongly to the host than less hindered amines, such as butylamine and propylamine; the recognition parameters for azetidine versus butylamine were found to be K = 22, DELTA-H-degrees = -2.6 kcal/mol, and T-DELTA-S-degrees = -0.8 kcal/mol at 25-degrees-C in toluene. However, the binding of the larger secondary amines such as dipropylamine and diisopropylamine to the host was weakened due to greater steric repulsions from the cavity. It was concluded that, in this case, the stabilization of the ligand binding by the geometrical complementarity between the amines and the cavity of the host is ascribed mainly to attractive interligand interactions such as the London force or CH-pi interaction.

  DOI：

  10.1021/ja00043a016
• 作为产物：
  描述：

  1,5-二溴戊烷 、 二羟基苯甲酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以39%的产率得到3,5-双(5-溴戊氧基)苯甲酸乙酯
  参考文献：
  名称：

  Recognition of axial ligands by a zinc porphyrin host on the basis of nonpolar interligand interaction

  摘要：

  A porphyrin host with a preorganized cavity on each face has been synthesized and characterized. The constants for association of the zinc complex of the porphyrin with various amine ligands were determined and compared with those of [meso-tetrakis(p-methylphenyl)porphyrinato]zinc(II) and of a "picket-fence" porphyrin zinc(II) complex. The selectivity for the amine ligands was not observed for the picket-fence porphyrin complex. Contrary to this, small secondary amines, such as azetidine, pyrrolidine, and diethylamine, that fit the shape of the cavity of the synthesized host complex bind more strongly to the host than less hindered amines, such as butylamine and propylamine; the recognition parameters for azetidine versus butylamine were found to be K = 22, DELTA-H-degrees = -2.6 kcal/mol, and T-DELTA-S-degrees = -0.8 kcal/mol at 25-degrees-C in toluene. However, the binding of the larger secondary amines such as dipropylamine and diisopropylamine to the host was weakened due to greater steric repulsions from the cavity. It was concluded that, in this case, the stabilization of the ligand binding by the geometrical complementarity between the amines and the cavity of the host is ascribed mainly to attractive interligand interactions such as the London force or CH-pi interaction.

  DOI：

  10.1021/ja00043a016

文献信息

• Recognition of axial ligands by a zinc porphyrin host on the basis of nonpolar interligand interaction
  作者：Hiroyasu Imai、Shigeo Nakagawa、Eishin Kyuno

  DOI：10.1021/ja00043a016

  日期：1992.8

  A porphyrin host with a preorganized cavity on each face has been synthesized and characterized. The constants for association of the zinc complex of the porphyrin with various amine ligands were determined and compared with those of [meso-tetrakis(p-methylphenyl)porphyrinato]zinc(II) and of a "picket-fence" porphyrin zinc(II) complex. The selectivity for the amine ligands was not observed for the picket-fence porphyrin complex. Contrary to this, small secondary amines, such as azetidine, pyrrolidine, and diethylamine, that fit the shape of the cavity of the synthesized host complex bind more strongly to the host than less hindered amines, such as butylamine and propylamine; the recognition parameters for azetidine versus butylamine were found to be K = 22, DELTA-H-degrees = -2.6 kcal/mol, and T-DELTA-S-degrees = -0.8 kcal/mol at 25-degrees-C in toluene. However, the binding of the larger secondary amines such as dipropylamine and diisopropylamine to the host was weakened due to greater steric repulsions from the cavity. It was concluded that, in this case, the stabilization of the ligand binding by the geometrical complementarity between the amines and the cavity of the host is ascribed mainly to attractive interligand interactions such as the London force or CH-pi interaction.