4-amino-2-hexyloxy-benzoic acid | 24397-14-6

• 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: 4-amino-2-hexyloxy-benzoic acid
• 英文别名: 2-n-Hexoxy-4-aminobenzoesaeure；4-Amino-2-(hexyloxy)benzoic acid；4-amino-2-hexoxybenzoic acid
• CAS: 24397-14-6
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: COOKBDDKTLVPGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 4-amino-2-hexyloxy-benzoic acid 反应 24.0h， 以89%的产率得到N-Fmoc-4-amino-2-hexyloxybenzoic acid
  参考文献：
  名称：

  Tuning the solubility of hepta(p-benzamide)s via the monomer sequence

  摘要：

  The automated synthesis of hepta(p-benzamide) heterosequences on solid support using a modified peptide synthesizer is reported. The oligomers are synthesized from 4-aminobenzoic acid and 4-amino-2-(hexyloxy)benzoic acid, the latter carrying a solubilizing hexyl side chain. It is known from previous studies that both the unsubstituted hepta(p-benzamide) and the fully hexyloxy-substituted hepta(p-benzamide) are insoluble in all common organic solvents. Heterosequences in which both types of monomers alternate are, however, soluble in polar organic solvents such as DMSO. The heterosequence heptamers behave as strong organogelators when DMSO solutions are left at room temperature for several hours. Transmission electron microscopic (TEM) investigations revealed that the gelation was due to the oligomers forming long entangled fibers via a non-covalent aggregation mechanism. We explain these phenomena by a heterosequence triggered switch of aggregation mechanism. The unsubstituted oligomers strongly aggregate via a directional hydrogen-bond driven mechanism which changes to a less directional pi-interaction driven aggregation mechanism for the substituted oligomers.We hereby demonstrate that designed heterosequences in non-natural oligoamides can lead to materials with distinctly different conformations which directly affect the intermolecular interactions and their supramolecular organization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.045
• 作为产物：
  描述：

  4-acetamido-2-hexyloxy-benzoic acid hexyl ester 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 50.0h， 以85%的产率得到4-amino-2-hexyloxy-benzoic acid
  参考文献：
  名称：

  Tuning the solubility of hepta(p-benzamide)s via the monomer sequence

  摘要：

  The automated synthesis of hepta(p-benzamide) heterosequences on solid support using a modified peptide synthesizer is reported. The oligomers are synthesized from 4-aminobenzoic acid and 4-amino-2-(hexyloxy)benzoic acid, the latter carrying a solubilizing hexyl side chain. It is known from previous studies that both the unsubstituted hepta(p-benzamide) and the fully hexyloxy-substituted hepta(p-benzamide) are insoluble in all common organic solvents. Heterosequences in which both types of monomers alternate are, however, soluble in polar organic solvents such as DMSO. The heterosequence heptamers behave as strong organogelators when DMSO solutions are left at room temperature for several hours. Transmission electron microscopic (TEM) investigations revealed that the gelation was due to the oligomers forming long entangled fibers via a non-covalent aggregation mechanism. We explain these phenomena by a heterosequence triggered switch of aggregation mechanism. The unsubstituted oligomers strongly aggregate via a directional hydrogen-bond driven mechanism which changes to a less directional pi-interaction driven aggregation mechanism for the substituted oligomers.We hereby demonstrate that designed heterosequences in non-natural oligoamides can lead to materials with distinctly different conformations which directly affect the intermolecular interactions and their supramolecular organization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.045

文献信息

• p-Aminobenzoic acid derivatives. Mode of action and structure-activity relations in a cell-free system (Escherichia coli)
  作者：J. K. Seydel、W. Butte

  DOI：10.1021/jm00213a023

  日期：1977.3

  studied in whole cell and cell-free systems. All studied derivatives form dihydropteroic acid analogues in the presence of a cell-free folate-synthesizing enzyme system. A thin-layer chromatographic system has been elaborated to determine the rate of analogue formation in the cell-free system. Physicochemical parameters of the PABA derivatives, such as pKa, pi, and Rm values, have been determined. These

  在全细胞和无细胞系统中，已经研究了核取代的对氨基苯甲酸（PABA）对大肠杆菌叶酸合成系统的激动作用和拮抗作用。所有研究的衍生物在无细胞叶酸合成酶系统的存在下形成二氢蝶呤酸类似物。精心设计了薄层色谱系统，以确定无细胞系统中类似物的形成速率。已经确定了PABA衍生物的理化参数，例如pKa，pi和Rm值。这些值已用于结构活性分析中，揭示了在不存在PABA的情况下类似物的形成速率与亲脂性无关。电离似乎是结合的决定性因素。由于所有研究的PABA衍生物在实验条件下均被完全电离，因此类似物的形成速率非常相似，不同之处在于2位带有大基团的化合物。因此，抑制能力的差异可能是由于类似物用作代谢产物的能力差异，还是由于与PABA的竞争。
• Tuning the solubility of hepta(p-benzamide)s via the monomer sequence
  作者：Helga Seyler、Andreas Kilbinger

  DOI：10.1016/j.tetlet.2012.11.045

  日期：2013.2

  The automated synthesis of hepta(p-benzamide) heterosequences on solid support using a modified peptide synthesizer is reported. The oligomers are synthesized from 4-aminobenzoic acid and 4-amino-2-(hexyloxy)benzoic acid, the latter carrying a solubilizing hexyl side chain. It is known from previous studies that both the unsubstituted hepta(p-benzamide) and the fully hexyloxy-substituted hepta(p-benzamide) are insoluble in all common organic solvents. Heterosequences in which both types of monomers alternate are, however, soluble in polar organic solvents such as DMSO. The heterosequence heptamers behave as strong organogelators when DMSO solutions are left at room temperature for several hours. Transmission electron microscopic (TEM) investigations revealed that the gelation was due to the oligomers forming long entangled fibers via a non-covalent aggregation mechanism. We explain these phenomena by a heterosequence triggered switch of aggregation mechanism. The unsubstituted oligomers strongly aggregate via a directional hydrogen-bond driven mechanism which changes to a less directional pi-interaction driven aggregation mechanism for the substituted oligomers.We hereby demonstrate that designed heterosequences in non-natural oligoamides can lead to materials with distinctly different conformations which directly affect the intermolecular interactions and their supramolecular organization. (C) 2012 Elsevier Ltd. All rights reserved.