4-(octadecyloxy)aniline hydrochloride | 67355-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(octadecyloxy)aniline hydrochloride
• 英文别名: 4-Octadecoxyaniline;hydrochloride；4-octadecoxyaniline;hydrochloride
• CAS: 67355-53-7
• 化学式: C₂₄H₄₃NO*ClH
• 分子量: 398.072
• InChiKey: VILAQNAKZGMQPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(chloroformyl)-cis,cis-1,3,5-trimethylcyclohexane-1,3-dicarboxylic anhydride 、 4-(octadecyloxy)aniline hydrochloride 以 氯仿 为溶剂， 反应 96.0h， 以17%的产率得到3,5-bis<<4-(octadecyloxy)phenyl>carbamoyl>-cis,cis-1,3,5-trimethylcyclohexane-1-carboxylic acid
  参考文献：
  名称：

  Molecular recognition at the air-water interface. Specific binding of nitrogen aromatics and amino acids by monolayers of long-chain derivatives of Kemp's acid

  摘要：

  Long-chain derivatives of Kemp's acid formed stable monolayers at the air-water interface, where the carboxylic acid groups produced the cyclic dimer species and served as a molecular cleft for specific binding of nitrogen aromatics and amino acids. The structure of the long-chain substituents was crucial for forming the cyclic dimer. Combinations of FT-IR, XPS, and UV spectroscopies of LB films and surface pressure-area isotherms revealed that substrates of complementary shape and functionality bound to the cleft mainly by hydrogen bonding. Phthalazine formed the 1:2 (substrate/amphiphile) complex, and enhanced binding of phthalazine (binding constant, 30 M-1) compared to that of quinazoline, quinoxaline, and pyridazine was ascribable to the proper location of nitrogen atoms within the molecule as well as smaller solubility in water. A more basic substrate, benzimidazole, bound to the monolayer 5 times more strongly probably in a form of the 1:1 complex. It is remarkable that significant substrate binding was attained even when the host monolayer and the substrates remained in exposure to the aqueous microenvironment. The monolayer of octadecanoic acid was not an effective receptor, implying that the convergent carboxylic acids were the intrinsic element of the molecular recognition.

  DOI：

  10.1021/ja00019a035
• 作为产物：
  描述：

  对乙酰氨基酚 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 42.0h， 生成 4-(octadecyloxy)aniline hydrochloride
  参考文献：
  名称：

  Molecular recognition at the air-water interface. Specific binding of nitrogen aromatics and amino acids by monolayers of long-chain derivatives of Kemp's acid

  摘要：

  Long-chain derivatives of Kemp's acid formed stable monolayers at the air-water interface, where the carboxylic acid groups produced the cyclic dimer species and served as a molecular cleft for specific binding of nitrogen aromatics and amino acids. The structure of the long-chain substituents was crucial for forming the cyclic dimer. Combinations of FT-IR, XPS, and UV spectroscopies of LB films and surface pressure-area isotherms revealed that substrates of complementary shape and functionality bound to the cleft mainly by hydrogen bonding. Phthalazine formed the 1:2 (substrate/amphiphile) complex, and enhanced binding of phthalazine (binding constant, 30 M-1) compared to that of quinazoline, quinoxaline, and pyridazine was ascribable to the proper location of nitrogen atoms within the molecule as well as smaller solubility in water. A more basic substrate, benzimidazole, bound to the monolayer 5 times more strongly probably in a form of the 1:1 complex. It is remarkable that significant substrate binding was attained even when the host monolayer and the substrates remained in exposure to the aqueous microenvironment. The monolayer of octadecanoic acid was not an effective receptor, implying that the convergent carboxylic acids were the intrinsic element of the molecular recognition.

  DOI：

  10.1021/ja00019a035