4-hydroxy-3-[1-(2-hydroxyphenylimino)-ethyl]-6-methylpyran-2-one | 32386-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-3-[1-(2-hydroxyphenylimino)-ethyl]-6-methylpyran-2-one
• 英文别名: 4-Hydroxy-3-[1-(2-hydroxy-phenylimino)-ethyl]-6-methyl-pyran-2-one；4-hydroxy-3-[N-(2-hydroxyphenyl)-C-methylcarbonimidoyl]-6-methylpyran-2-one
• CAS: 32386-76-8
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: BIHMLNAESZOYRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-[1-(2-hydroxyphenylimino)-ethyl]-6-methylpyran-2-one 、 二丁基二氯化硅 在 sodium 作用下， 以 乙醇 为溶剂， 以74%的产率得到
  参考文献：
  名称：

  Synthesis, antimicrobial activities and QSAR studies of heterocyclic Schiff base ligands with organosilicon(IV) halides

  摘要：

  A series of heterocyclic Schiff base ligands 4-hydroxy-3-[1-{(2-hydroxy-aryl) imino}-ethyl]-6-methyl-pyran-2-one; aryl = phenyl, 4-methylphenyl, 4-chlorophenyl or 4-nitrophenyl (1-4) and their organosilicon(IV) complexes R2Si(L) (R = Et, Bu or Ph) (5-16) were synthesized and characterized. The elemental analyses, molar conductance and spectral (IR, H-1, C-13 and Si-29 NMR) data suggested pentacoordinated environment around the silicon atom, where tridentate ligands coordinate through the azomethine nitrogen and oxygen of hydroxyl groups. The ligands and their organosilicon complexes were tested in vitro against pathogenic bacteria and fungi to assess their antimicrobial properties. The activity of the ligands improved against most of the strains of the tested microorganisms on complexation to the organosilicon groups. The antimicrobial activities were correlated with QSAR studies using the linear free energy relationship model which indicate the importance of topological parameters, third-order and valence first-order molecular connectivity indices ((3) chi (v) and (1) chi (v) ), to explain the antibacterial and antifungal activities of all synthesized compounds.

  DOI：

  10.1007/s00044-015-1478-6
• 作为产物：
  描述：

  去氢乙酸 、 2-氨基苯酚 以 乙醇 为溶剂， 反应 0.5h， 以80%的产率得到4-hydroxy-3-[1-(2-hydroxyphenylimino)-ethyl]-6-methylpyran-2-one
  参考文献：
  名称：

  Synthesis, antimicrobial activities and QSAR studies of heterocyclic Schiff base ligands with organosilicon(IV) halides

  摘要：

  A series of heterocyclic Schiff base ligands 4-hydroxy-3-[1-{(2-hydroxy-aryl) imino}-ethyl]-6-methyl-pyran-2-one; aryl = phenyl, 4-methylphenyl, 4-chlorophenyl or 4-nitrophenyl (1-4) and their organosilicon(IV) complexes R2Si(L) (R = Et, Bu or Ph) (5-16) were synthesized and characterized. The elemental analyses, molar conductance and spectral (IR, H-1, C-13 and Si-29 NMR) data suggested pentacoordinated environment around the silicon atom, where tridentate ligands coordinate through the azomethine nitrogen and oxygen of hydroxyl groups. The ligands and their organosilicon complexes were tested in vitro against pathogenic bacteria and fungi to assess their antimicrobial properties. The activity of the ligands improved against most of the strains of the tested microorganisms on complexation to the organosilicon groups. The antimicrobial activities were correlated with QSAR studies using the linear free energy relationship model which indicate the importance of topological parameters, third-order and valence first-order molecular connectivity indices ((3) chi (v) and (1) chi (v) ), to explain the antibacterial and antifungal activities of all synthesized compounds.

  DOI：

  10.1007/s00044-015-1478-6