8-<3,5-Bis(2-hydroxy-3-phenylphenyl)phenyl>-2-methyl-5-nitroquinoline | 151443-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-<3,5-Bis(2-hydroxy-3-phenylphenyl)phenyl>-2-methyl-5-nitroquinoline
• CAS: 151443-97-9
• 化学式: C₄₀H₂₈N₂O₄
• 分子量: 600.673
• InChiKey: IMRQMLYWLADHLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  46.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  96.49
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  8-<3,5-Bis(2-hydroxy-3-phenylphenyl)phenyl>-2-methyl-5-nitroquinoline 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Receptors for oxo acids: effects of intra-ion-pair hydrogen bonding on acid-base equilibria

  摘要：

  Receptor molecules 1-3 containing a quinoline unit and hydroxyl groups were synthesized, and their properties in salt formation with oxo acids such as p-toluenesulfonic acid (TsOH) and methyl phenylphosphonate (MPP) were studied by using H-1 NMR spectroscopy. In CDCl3 solution the salt formation of the receptors with TsOH or MPP is enhanced by hydrogen bonds between the hydroxyl groups and the counteranion. The salt-formation enhancement of 1 over 2 suggests the presence of multiple interactions. The X-ray structure of 1.MPP.(acetone)2 confirms that three hydrogen-bonding interactions stabilize the salt. In the salt formation of 5-(dimethylamino)quinoline derivative 3, the hydroxyl groups also affect the relative basicity of the basic nitrogens in 3. The results described here emphasize that acid-base equilibria in apolar solvents are significantly affected by intra-ion-pair hydrogen bonding (i.e., hydrogen bonding within a contact ion pair).

  DOI：

  10.1021/jo00076a031
• 作为产物：
  描述：

  8-溴-2-甲基喹啉 在 盐酸 、 四(三苯基膦)钯 、 硫酸 、 硝酸 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 33.0h， 生成 8-<3,5-Bis(2-hydroxy-3-phenylphenyl)phenyl>-2-methyl-5-nitroquinoline
  参考文献：
  名称：

  Receptors for oxo acids: effects of intra-ion-pair hydrogen bonding on acid-base equilibria

  摘要：

  Receptor molecules 1-3 containing a quinoline unit and hydroxyl groups were synthesized, and their properties in salt formation with oxo acids such as p-toluenesulfonic acid (TsOH) and methyl phenylphosphonate (MPP) were studied by using H-1 NMR spectroscopy. In CDCl3 solution the salt formation of the receptors with TsOH or MPP is enhanced by hydrogen bonds between the hydroxyl groups and the counteranion. The salt-formation enhancement of 1 over 2 suggests the presence of multiple interactions. The X-ray structure of 1.MPP.(acetone)2 confirms that three hydrogen-bonding interactions stabilize the salt. In the salt formation of 5-(dimethylamino)quinoline derivative 3, the hydroxyl groups also affect the relative basicity of the basic nitrogens in 3. The results described here emphasize that acid-base equilibria in apolar solvents are significantly affected by intra-ion-pair hydrogen bonding (i.e., hydrogen bonding within a contact ion pair).

  DOI：

  10.1021/jo00076a031