3-(2-chloro-4-fluorophenyl)-7-(3,4-dicyanophenoxy)coumarin | 1202694-03-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(2-chloro-4-fluorophenyl)-7-(3,4-dicyanophenoxy)coumarin
• 英文别名: 4-[3-(2-Chloro-4-fluorophenyl)-2-oxochromen-7-yl]oxybenzene-1,2-dicarbonitrile；4-[3-(2-chloro-4-fluorophenyl)-2-oxochromen-7-yl]oxybenzene-1,2-dicarbonitrile
• CAS: 1202694-03-8
• 化学式: C₂₃H₁₀ClFN₂O₃
• 分子量: 416.795
• InChiKey: HHBWPRDNOJKFRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-chloro-4-fluorophenyl)-7-(3,4-dicyanophenoxy)coumarin 、 zinc(II) acetate dihydrate 以 further solvent(s) 为溶剂， 以33.64%的产率得到2(3),9(10),16(17),23(24)-tetrakis[7-oxo-3-(2-chloro-4-fluorophenyl)coumarin]phthalocyaninato zinc(II)
  参考文献：
  名称：

  Synthesis, spectroscopy, electrochemistry and in situ spectroelectrochemistry of partly halogenated coumarin phthalonitrile and corresponding metal-free, cobalt and zinc phthalocyanines

  摘要：

  In this study, the preparation of novel 7-hydroxy-3-(2-chloro-4-fluorophenyl)coumarin (1), the ligand, 7-(3,4-dicyanophenoxy)-3-(2-chloro-4-fluorophenyl)coumarin (2), metal-free phthalocyanine 3 and metallophthalocyanine complexes 4 and 5 (MPcs, M = Co, Zn), beta-substituted with 7-oxo-3-(2-chloro-4fluorophenyl)coumarin functional group was achieved. By the reaction of 7-hydroxy-3-(2-chloro-4-fluorophenyl)coumarin (1) with 1,2-dicyano-4-nitrobenzen in dry DMF as the solvent in the presence of K2CO3 as the base, the 7-(3,4-dicyanophenoxy)-3-(2-chloro-4-fluorophenyl)coumarin (2) was synthesized. Compound 2 reacted with Co(CH3COO)2 center dot 4H(2)O in 2-N,N-dimethylaminoethanol to furnish a novel coumarin containing cobalt(II) Phthalocyanine 4. The cyclotetramerization of 2 with Zn(CH3COO)(2)center dot 2H(2)O in 2-N,N-dimethylaminoethanol gave the novel coumarin containing Zn(II)phthalocyanine 5; while tetramerization without any metal salts in 2-N,N-dimethylaminoethanol gave the metal-free phthalocyanine 3. The structures of obtained compounds were confirmed by elemental analysis. UV-Vis, IR, MALDI-TOF mass and H-1 NMR spectra. The cyclic and differential pulse voltammetry, and in situ spectroelectrochemistry of 7-oxo-3-(2-chloro-4-fuorophenyl)coumarin substituted phthalocyanines 3, 4 and 5 allowed us to identify metal- and phthalocyanine ring-based redox processes of the complexes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.07.060

文献信息

• Synthesis, spectroscopy, electrochemistry and in situ spectroelectrochemistry of partly halogenated coumarin phthalonitrile and corresponding metal-free, cobalt and zinc phthalocyanines
  作者：Aydın Alemdar、Ali Rıza Özkaya、Mustafa Bulut

  DOI：10.1016/j.poly.2009.07.060

  日期：2009.11

  In this study, the preparation of novel 7-hydroxy-3-(2-chloro-4-fluorophenyl)coumarin (1), the ligand, 7-(3,4-dicyanophenoxy)-3-(2-chloro-4-fluorophenyl)coumarin (2), metal-free phthalocyanine 3 and metallophthalocyanine complexes 4 and 5 (MPcs, M = Co, Zn), beta-substituted with 7-oxo-3-(2-chloro-4fluorophenyl)coumarin functional group was achieved. By the reaction of 7-hydroxy-3-(2-chloro-4-fluorophenyl)coumarin (1) with 1,2-dicyano-4-nitrobenzen in dry DMF as the solvent in the presence of K2CO3 as the base, the 7-(3,4-dicyanophenoxy)-3-(2-chloro-4-fluorophenyl)coumarin (2) was synthesized. Compound 2 reacted with Co(CH3COO)2 center dot 4H(2)O in 2-N,N-dimethylaminoethanol to furnish a novel coumarin containing cobalt(II) Phthalocyanine 4. The cyclotetramerization of 2 with Zn(CH3COO)(2)center dot 2H(2)O in 2-N,N-dimethylaminoethanol gave the novel coumarin containing Zn(II)phthalocyanine 5; while tetramerization without any metal salts in 2-N,N-dimethylaminoethanol gave the metal-free phthalocyanine 3. The structures of obtained compounds were confirmed by elemental analysis. UV-Vis, IR, MALDI-TOF mass and H-1 NMR spectra. The cyclic and differential pulse voltammetry, and in situ spectroelectrochemistry of 7-oxo-3-(2-chloro-4-fuorophenyl)coumarin substituted phthalocyanines 3, 4 and 5 allowed us to identify metal- and phthalocyanine ring-based redox processes of the complexes. (C) 2009 Elsevier Ltd. All rights reserved.