p-(2,3-dicyanophenoxy)phenylacetic acid | 1193356-71-6

• 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: p-(2,3-dicyanophenoxy)phenylacetic acid
• 英文别名: 4-(2,3-dicyanophenoxy)phenylacetic acid；2-[4-(2,3-Dicyanophenoxy)phenyl]acetic acid；2-[4-(2,3-dicyanophenoxy)phenyl]acetic acid
• CAS: 1193356-71-6
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: ZZUUUDVBFLLPNH-UHFFFAOYSA-N

物化性质

• 熔点：
  178-183 °C
• 沸点：
  507.7±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-(2,3-dicyanophenoxy)phenylacetic acid 在 盐酸 作用下， 以 水 、 乙酸酐 为溶剂， 反应 26.0h， 生成 7,8-dihydroxy-3-[p-(2',3'-dicyanophenoxy)phenyl]coumarin
  参考文献：
  名称：

  用于单重态氧生产的带香豆素的12皇冠4酞菁光敏剂

  摘要：

  在外围位置（配合物3a和3b）和在非外围位置（配合物4a和4b）具有7,8-（首次报道了12-冠-4）-3-（4-氧苯基）香豆素基团。这些新化合物已通过元素分析FT-IR表征11 H NMR，电子光谱和质谱。描述了光降解，单线态氧和荧光量子产率以及这些化合物在二甲亚砜（DMSO）中的荧光寿命的一般趋势。酞菁配合物的光物理和光化学特性对于光动力疗法（PDT）应用非常有用。单线态氧量子产率（Φ Δ范围从0.11至0.80）的指示络合物作为光敏剂的PDT中的应用的潜力。

  DOI：

  10.1016/j.jphotochem.2011.06.007
• 作为产物：
  描述：

  对羟基苯乙酸 、 3-硝基邻苯二腈 在 potassium carbonate 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 72.0h， 生成 p-(2,3-dicyanophenoxy)phenylacetic acid
  参考文献：
  名称：

  Synthesis, characterization and comparative studies on the photophysical and photochemical properties of metal-free and zinc(II) phthalocyanines with phenyloxyacetic acid functionalities

  摘要：

  The synthesis and characterization of new peripherally and non-peripherally tetra-substituted metal-free and zinc(II) phthalocyanines with 2-, 3- and 4-phenyloxyacetic acid functionalities are described for the first time in this study. The new compounds have been characterized by elemental analysis, FT-IR, UV-Vis, MALDI-TOF and H-1-NMR spectra. Photodegradation, singlet oxygen and fluorescence quantum yields, and fluorescence lifetimes of these compounds are studied in dimethylformamide (DMF). The influence of the substituent position on the phthalocyanine framework (non-peripherally or peripherally), central metal ion (metal-free or zinc) and the position of the COOH group (2-, 3- or 4-position on the phenyloxyacetic acid) on the spectroscopic, photophysical and photochemical properties have been investigated. Non-peripherally zinc(II) phthalocyanines (1b and 2b) and peripherally zinc(II) phthalocyanine (4b) gave good singlet oxygen quantum yields (phi(Delta)) (0.37, 0.39 and 0.38, respectively) which indicate the potential of the complexes as photosensitizers in applications of PDT. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.04.044

文献信息

• Preparation, characterization and photophysicochemical properties of novel tetra 7-(diethyl 2-methylmalonatoxy)-3-(p-oxyphenyl)coumarin-substituted zinc(II) and indium(III)chloride phthalocyanines
  作者：Meryem Aygün Köksoy、Baybars Köksoy、Mahmut Durmuş、Mustafa Bulut

  DOI：10.1016/j.jorganchem.2016.08.009

  日期：2016.11

  2-methylmalonatoxy)-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin (4) and their related peripheral and non-peripheral tetra substituted zinc(II) (3a and 4a) and indium(III)chloride (3b and 4b) phthalocyanine derivatives were prepared for the first time. The novel phthalonitrile (3 and 4) and phthalocyanine (3a-b and 4a-b) compounds were characterized by elemental analyses and different spectroscopic techniques

  在这项研究中，7-（2-乙基2-甲基丙二酰氧基）-3- [ p-（3,4-二氰基苯氧基）苯基]香豆素（3），7-（2-乙基2-甲基丙二酰氧基）-3- [ p-（2,3首次制备了-二氰基苯氧基）苯基]香豆素（4）及其相关的外围和非外围四取代锌（II）（3a和4a）和氯化铟（III）（3b和4b）酞菁衍生物。新型酞腈（3和4）和酞菁（3a - b和4a - b））化合物通过元素分析和不同的光谱技术（例如FT-IR，UV-vis，1 H NMR和MALDI-TOF质量）进行表征。在二甲亚砜溶液中研究了这些新型酞菁的光谱，光物理（荧光量子产率和寿命）和光化学（单氧生成和光降解）。还确定了1,4-苯醌对所研究的酞菁锌（II）（3a和4a）的荧光猝灭行为。
• Synthesis, characterization and comparative studies on the photophysical and photochemical properties of metal-free and zinc(II) phthalocyanines with phenyloxyacetic acid functionalities
  作者：Meryem Çamur、Mahmut Durmuş、Mustafa Bulut

  DOI：10.1016/j.poly.2011.04.044

  日期：2011.8

  The synthesis and characterization of new peripherally and non-peripherally tetra-substituted metal-free and zinc(II) phthalocyanines with 2-, 3- and 4-phenyloxyacetic acid functionalities are described for the first time in this study. The new compounds have been characterized by elemental analysis, FT-IR, UV-Vis, MALDI-TOF and H-1-NMR spectra. Photodegradation, singlet oxygen and fluorescence quantum yields, and fluorescence lifetimes of these compounds are studied in dimethylformamide (DMF). The influence of the substituent position on the phthalocyanine framework (non-peripherally or peripherally), central metal ion (metal-free or zinc) and the position of the COOH group (2-, 3- or 4-position on the phenyloxyacetic acid) on the spectroscopic, photophysical and photochemical properties have been investigated. Non-peripherally zinc(II) phthalocyanines (1b and 2b) and peripherally zinc(II) phthalocyanine (4b) gave good singlet oxygen quantum yields (phi(Delta)) (0.37, 0.39 and 0.38, respectively) which indicate the potential of the complexes as photosensitizers in applications of PDT. (C) 2011 Elsevier Ltd. All rights reserved.
• Coumarino-12-crown-4 bearing phthalocyanine photosensitizers for singlet oxygen production
  作者：Meryem Çamur、Mahmut Durmuş、Mustafa Bulut

  DOI：10.1016/j.jphotochem.2011.06.007

  日期：2011.7

  photochemical properties of the new metal-free and zinc (II) phthalocyanines tetra-substituted at the peripheral (complexes 3a and 3b) and non-peripheral (complexes 4a and 4b) positions with 7,8-(12-crown-4)-3-(4-oxyphenyl)coumarin groups are reported for the first time. The new compounds have been characterized by elemental analysis, FT-IR, 1H NMR, electronic spectroscopy and mass spectra. General trends

  在外围位置（配合物3a和3b）和在非外围位置（配合物4a和4b）具有7,8-（首次报道了12-冠-4）-3-（4-氧苯基）香豆素基团。这些新化合物已通过元素分析FT-IR表征11 H NMR，电子光谱和质谱。描述了光降解，单线态氧和荧光量子产率以及这些化合物在二甲亚砜（DMSO）中的荧光寿命的一般趋势。酞菁配合物的光物理和光化学特性对于光动力疗法（PDT）应用非常有用。单线态氧量子产率（Φ Δ范围从0.11至0.80）的指示络合物作为光敏剂的PDT中的应用的潜力。