dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate | 1242417-55-5

• 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: dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate
• 英文别名: dimethyl 5-amino-2-hydroxy-4,6-dimethylbenzene-1,3-dicarboxylate
• CAS: 1242417-55-5
• 化学式: C₁₂H₁₅NO₅
• 分子量: 253.255
• InChiKey: HKIQWQJTBBADIA-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  372.8±42.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate 、 对乙酰胺基苯磺酰氯 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 以75%的产率得到dimethyl 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethylisophthalate
  参考文献：
  名称：

  Synthesis of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophthalates and Their Sulfonylation

  摘要：

  Dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate and dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate were obtained in the free form for the first time. The products were sulfonylated with p-toluenesulfonyl to obtain previously unknown dialkyl 5-(4-toluenesulfonamido)-2-hydroxy-4,6-dimethylisophthalates. The use of p-acetamidobenzenesulfonyl chloride as the sulfonylating agent in this reaction led to the formation of dialkyl 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethyl isophthalates. The synthesized sulfonamide derivatives are of interest as potentially biologically active compounds. The structure of all the obtained compounds was proved using IR and NMR spectroscopy and mass spectrometry.

  DOI：

  10.1134/s1070428019050269
• 作为产物：
  描述：

  potassium 2,6-bis(methoxycarbonyl)-3,5-dimethyl-4-nitrosophenoxide 在 sodium oxalate 作用下， 以 水 为溶剂， 反应 1.0h， 以42%的产率得到dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate
  参考文献：
  名称：

  Synthesis of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophthalates and Their Sulfonylation

  摘要：

  Dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate and dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate were obtained in the free form for the first time. The products were sulfonylated with p-toluenesulfonyl to obtain previously unknown dialkyl 5-(4-toluenesulfonamido)-2-hydroxy-4,6-dimethylisophthalates. The use of p-acetamidobenzenesulfonyl chloride as the sulfonylating agent in this reaction led to the formation of dialkyl 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethyl isophthalates. The synthesized sulfonamide derivatives are of interest as potentially biologically active compounds. The structure of all the obtained compounds was proved using IR and NMR spectroscopy and mass spectrometry.

  DOI：

  10.1134/s1070428019050269

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 of Dialkyl 5-Amino-2-hydroxy-4,6-dimethylisophthalates and Their Sulfonylation
  作者：I. G. Povarov、N. A. Shilenkov、I. V. Peterson、G. A. Suboch、M. S. Tovbis

  DOI：10.1134/s1070428019050269

  日期：2019.5

  Dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate and dimethyl 5-amino-2-hydroxy-4,6-dimethylisophthalate were obtained in the free form for the first time. The products were sulfonylated with p-toluenesulfonyl to obtain previously unknown dialkyl 5-(4-toluenesulfonamido)-2-hydroxy-4,6-dimethylisophthalates. The use of p-acetamidobenzenesulfonyl chloride as the sulfonylating agent in this reaction led to the formation of dialkyl 5-(4-acetamidobenzenesulfonamido)-2-hydroxy-4,6-dimethyl isophthalates. The synthesized sulfonamide derivatives are of interest as potentially biologically active compounds. The structure of all the obtained compounds was proved using IR and NMR spectroscopy and mass spectrometry.
• 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.