dipropyl 5-amino-2-hydroxy-4,6-dimethylisophthalate | 1242417-57-7

• 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: dipropyl 5-amino-2-hydroxy-4,6-dimethylisophthalate
• 英文别名: dipropyl 5-amino-2-hydroxy-4,6-dimethylbenzene-1,3-dicarboxylate
• CAS: 1242417-57-7
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: KBUMAJPSLNXSAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dipropyl 5-amino-2-hydroxy-4,6-dimethylisophthalate 、 对乙酰胺基苯磺酰氯 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 3.0h， 以45%的产率得到dipropyl 5-[(4-acetamido)benzenesulfonamido]-2-hydroxy-4,6-dimethylisophthalate
  参考文献：
  名称：

  Synthesis, Acid–Base Properties, and Sulfonylation of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophtalates

  摘要：

  Dialkyl 5-amino-2-hydroxy-4,6-dimethylisophthalates were synthesized for the first time by the reduction of the corresponding nitroso derivatives with sodium dithionite. The pK(a)and pK(BH+)values of the synthesized compounds were determined and taken into account to find conditions for their sulfonylation withp-toluenesulfonyl chloride andp-acetamidobenzenesulfonyl chloride. As a result, previously unknown sulfonylated derivatives of substituted aminoisophthalates with potential antimicrobial properties were obtained. The composition and structure of the products were confirmed by IR, UV, and(1)H NMR spectroscopy and mass spectrometry. The geometric structure of the sulfonylated compounds was established by DFT calculations at the BP86-D3/def2-SVP level of theory. The antibacterial effect of 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethylisophthalate was revealed.

  DOI：

  10.1134/s1070428020080126
• 作为产物：
  描述：

  dipropyl 2-hydroxy-4,6-dimethyl-5-nitrosobenzene-1,3-dicarboxylate 在 0.5% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 dipropyl 5-amino-2-hydroxy-4,6-dimethylisophthalate
  参考文献：
  名称：

  Catalytic hydrogenation of persubstituted p-nitrosophenols

  摘要：

  Catalytic hydrogenation of dialkyl 2-hydroxy-4,6-dimethyl-5-nitrosobenzene-1,3-dicarboxylates over Pd/C gave the corresponding previously unknown dialkyl 5-amino-2-hydroxy-4,6-dimethylbenzene-1,3-dicarboxylates. The first-order rate constants for the hydrogenation process were found to be linearly related to steric constants of the alkyl groups.

  DOI：

  10.1134/s1070428010040111

文献信息

• Catalytic hydrogenation of persubstituted p-nitrosophenols
  作者：D. G. Slashchinin、M. S. Tovbis、E. V. Root、V. E. Zadov、V. A. Sokolenko

  DOI：10.1134/s1070428010040111

  日期：2010.4

  Catalytic hydrogenation of dialkyl 2-hydroxy-4,6-dimethyl-5-nitrosobenzene-1,3-dicarboxylates over Pd/C gave the corresponding previously unknown dialkyl 5-amino-2-hydroxy-4,6-dimethylbenzene-1,3-dicarboxylates. The first-order rate constants for the hydrogenation process were found to be linearly related to steric constants of the alkyl groups.
• Synthesis, Acid–Base Properties, and Sulfonylation of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophtalates
  作者：I. G. Povarov、N. A. Shilenkov、P. O. Krasnov、G. A. Suboch、M. S. Tovbis

  DOI：10.1134/s1070428020080126

  日期：2020.8

  Dialkyl 5-amino-2-hydroxy-4,6-dimethylisophthalates were synthesized for the first time by the reduction of the corresponding nitroso derivatives with sodium dithionite. The pK(a)and pK(BH+)values of the synthesized compounds were determined and taken into account to find conditions for their sulfonylation withp-toluenesulfonyl chloride andp-acetamidobenzenesulfonyl chloride. As a result, previously unknown sulfonylated derivatives of substituted aminoisophthalates with potential antimicrobial properties were obtained. The composition and structure of the products were confirmed by IR, UV, and(1)H NMR spectroscopy and mass spectrometry. The geometric structure of the sulfonylated compounds was established by DFT calculations at the BP86-D3/def2-SVP level of theory. The antibacterial effect of 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethylisophthalate was revealed.