4',5-dibenzyl-naringenin-7-O-4-phthalonitrile | 1202524-77-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4',5-dibenzyl-naringenin-7-O-4-phthalonitrile
• 英文别名: 5-benzyl-naringenin-7-O-4-phthalonitrile；4-[[5-Hydroxy-4-oxo-2-(4-phenylmethoxyphenyl)-2,3-dihydrochromen-7-yl]oxy]benzene-1,2-dicarbonitrile；4-[[5-hydroxy-4-oxo-2-(4-phenylmethoxyphenyl)-2,3-dihydrochromen-7-yl]oxy]benzene-1,2-dicarbonitrile
• CAS: 1202524-77-3
• 化学式: C₃₀H₂₀N₂O₅
• 分子量: 488.499
• InChiKey: ZLVDLLJNFYSISV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4',5-dibenzyl-naringenin-7-O-4-phthalonitrile 、 1,2-二氰基苯 在 N,N-二甲基乙醇胺 、 zinc(II) chloride 作用下， 反应 4.0h， 以55%的产率得到2-naringenin-7-O-phthalocyaninatozinc(II)
  参考文献：
  名称：

  Synthesis and characterization of novel flavonoid-substituted phthalocyanines using (±)naringenin

  摘要：

  In this study, novel unsymmetrical mono- and di-substituted metal free and metallo phthalocyanines containing peripheral naringeninoxy moieties have been prepared. The naringenin-substituted phthalonitrile was synthesized from 4-nitrophthalonitrile and (+/-)naringenin in dimethylsulfoxide. Preparation of unsymmetrical mono-and di-substituted phthalocyanines, 2-naringenin-7-O-phthalocyaninatozinc, 2,9-bis-naringenin-7-O-phthalocyaninatozinc, 2,9-bis-naringenin-7-O-phthalocyaninatocobalt and 2,9-bisnaringenin-7-O-phthalocyanine was performed at 120-140 degrees C using the corresponding phthalonitrile in the presence of N,N-dimethylethanolamine (DMAE), ZnCl2, CoCl2 and LiCl, respectively. Synthesized new phthalocyanine compounds have been characterized by elemental analysis and H-1 NMR, C-13 NMR, FT-IR, MS and UV-vis spectroscopy. These are the first known examples of flavonoid-substituted phthalocyanines. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.09.012
• 作为产物：
  描述：

  naringenin-7-O-4-phthalonitrile 、 氯化苄 在 potassium carbonate 、 potassium iodide 、 盐酸 、 水 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以34%的产率得到4',5-dibenzyl-naringenin-7-O-4-phthalonitrile
  参考文献：
  名称：

  Synthesis and characterization of novel flavonoid-substituted phthalocyanines using (±)naringenin

  摘要：

  In this study, novel unsymmetrical mono- and di-substituted metal free and metallo phthalocyanines containing peripheral naringeninoxy moieties have been prepared. The naringenin-substituted phthalonitrile was synthesized from 4-nitrophthalonitrile and (+/-)naringenin in dimethylsulfoxide. Preparation of unsymmetrical mono-and di-substituted phthalocyanines, 2-naringenin-7-O-phthalocyaninatozinc, 2,9-bis-naringenin-7-O-phthalocyaninatozinc, 2,9-bis-naringenin-7-O-phthalocyaninatocobalt and 2,9-bisnaringenin-7-O-phthalocyanine was performed at 120-140 degrees C using the corresponding phthalonitrile in the presence of N,N-dimethylethanolamine (DMAE), ZnCl2, CoCl2 and LiCl, respectively. Synthesized new phthalocyanine compounds have been characterized by elemental analysis and H-1 NMR, C-13 NMR, FT-IR, MS and UV-vis spectroscopy. These are the first known examples of flavonoid-substituted phthalocyanines. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.09.012

文献信息

• Synthesis and characterization of novel flavonoid-substituted phthalocyanines using (±)naringenin
  作者：S. Zeki Yıldız、Mustafa Küçükislamoğlu、Murat Tuna

  DOI：10.1016/j.jorganchem.2009.09.012

  日期：2009.12

  In this study, novel unsymmetrical mono- and di-substituted metal free and metallo phthalocyanines containing peripheral naringeninoxy moieties have been prepared. The naringenin-substituted phthalonitrile was synthesized from 4-nitrophthalonitrile and (+/-)naringenin in dimethylsulfoxide. Preparation of unsymmetrical mono-and di-substituted phthalocyanines, 2-naringenin-7-O-phthalocyaninatozinc, 2,9-bis-naringenin-7-O-phthalocyaninatozinc, 2,9-bis-naringenin-7-O-phthalocyaninatocobalt and 2,9-bisnaringenin-7-O-phthalocyanine was performed at 120-140 degrees C using the corresponding phthalonitrile in the presence of N,N-dimethylethanolamine (DMAE), ZnCl2, CoCl2 and LiCl, respectively. Synthesized new phthalocyanine compounds have been characterized by elemental analysis and H-1 NMR, C-13 NMR, FT-IR, MS and UV-vis spectroscopy. These are the first known examples of flavonoid-substituted phthalocyanines. (C) 2009 Elsevier B.V. All rights reserved.