6-(3,4-dicyanophenoxy)-4-methylcoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-(3,4-dicyanophenoxy)-4-methylcoumarin
• 英文别名: 4-(4-Methyl-2-oxochromen-6-yl)oxybenzene-1,2-dicarbonitrile；4-(4-methyl-2-oxochromen-6-yl)oxybenzene-1,2-dicarbonitrile
• 化学式: C₁₈H₁₀N₂O₃
• 分子量: 302.289
• InChiKey: SLTUZUUEXIXJJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(3,4-dicyanophenoxy)-4-methylcoumarin 在 N,N-二甲基乙醇胺 作用下， 反应 48.0h， 以67%的产率得到2,9,16,23-tetrakis(4-methylcoumarin-6-yloxy)phthalocyanine
  参考文献：
  名称：

  新型抗菌金属无金属和附加四种外周香豆素衍生物的金属酞菁的合成及其结构异构体的分离

  摘要：

  The preparation of novel metal-free phthalocyanines and metallophthalocyanine complexes 6 and 7 (MPcs, M = Co, Zn, Cu and Mn), with four peripheral 6-hydroxy-4-methylcoumarin and 6-hydroxycoumarin substituents, were prepared by cyclotetramerization of compounds 4 and 5 with the corresponding metal salts (Zn(OAc)(2)center dot 2H(2)O, Co(OAc)(2)center dot 4H(2)O, CuCl, Mn(OAc)(2)center dot 4H(2)O) as a template for macrocycle formation in 2-(N,N-dimethylamino)ethanol whereby a mixture of four different structural isomers is obtained; two of these isomers, with C2 ''- and Cs-symmetry are isolated by HPLC and characterized by FT-IR, UV-vis, elemental analyses, H-1 NMR and C-13 NMR spectroscopies. The electronic spectra exhibit a band of coumarin identity together with characteristic bands of the phthalocyanine core. The new compounds were screened for antibacterial activity. Most of them are more active against E. coli and S. aureus.

  DOI：

  10.3987/com-13-12816
• 作为产物：
  描述：

  6-羟基-4-甲基香豆素 、 4-硝基邻苯二甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.25h， 以93%的产率得到6-(3,4-dicyanophenoxy)-4-methylcoumarin
  参考文献：
  名称：

  新型抗菌金属无金属和附加四种外周香豆素衍生物的金属酞菁的合成及其结构异构体的分离

  摘要：

  The preparation of novel metal-free phthalocyanines and metallophthalocyanine complexes 6 and 7 (MPcs, M = Co, Zn, Cu and Mn), with four peripheral 6-hydroxy-4-methylcoumarin and 6-hydroxycoumarin substituents, were prepared by cyclotetramerization of compounds 4 and 5 with the corresponding metal salts (Zn(OAc)(2)center dot 2H(2)O, Co(OAc)(2)center dot 4H(2)O, CuCl, Mn(OAc)(2)center dot 4H(2)O) as a template for macrocycle formation in 2-(N,N-dimethylamino)ethanol whereby a mixture of four different structural isomers is obtained; two of these isomers, with C2 ''- and Cs-symmetry are isolated by HPLC and characterized by FT-IR, UV-vis, elemental analyses, H-1 NMR and C-13 NMR spectroscopies. The electronic spectra exhibit a band of coumarin identity together with characteristic bands of the phthalocyanine core. The new compounds were screened for antibacterial activity. Most of them are more active against E. coli and S. aureus.

  DOI：

  10.3987/com-13-12816