4-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile | 1395920-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile
• CAS: 1395920-43-0
• 化学式: C₁₃H₅F₉N₂O₃
• 分子量: 408.18
• InChiKey: UCYLQXUGSJIGLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.27
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tetrabutoxytitanium 、 4-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile 在 尿素 作用下， 以 辛醇 为溶剂， 反应 7.0h， 以19%的产率得到2(3),9(10),16(17)23(24)-tetrakis{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalocyaninato oxo-titanium(IV)
  参考文献：
  名称：

  Photophysical and photochemical properties of fluoroether-substituted zinc(II) and titanium(IV) phthalocyanines

  摘要：

  本文首次描述了带有 1H,1H-nona?uoro-3,6-dioxaheptan-1-ol 基团的新型锌（II）（1a-4a）和氧代钛（IV）（1b-4b）酞菁衍生物的合成和表征。这些酞菁（1a-4a 和 1b-4b）通过元素分析和不同的光谱技术（如紫外-可见光、[式：见正文]H NMR、傅立叶变换红外光谱和质量）进行了表征。此外，还研究了这些酞菁在四氢呋喃（THF）溶液中的光物理（荧光量子产率和寿命）和光化学（单线态氧生成和光降解）特性。评估了取代基的数目（四或八）、取代基的位置（外围或非外围）以及中心金属原子（锌或钛）对这些酞菁的光物理和光化学特性的影响。

  DOI：

  10.1142/s1088424618500074
• 作为产物：
  描述：

  1H,1H-九氟-3,6-二噁-1-庚醇 、 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 72.0h， 以66%的产率得到4-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile
  参考文献：
  名称：

  Synthesis and characterization of novel fluoroether-substituted phthalocyanines

  摘要：

  The synthesis of 1H,1H-nonafluoro-3,6-dioxaheptan-1-ol with 4-nitrophthalonitrile and 4,5-dichlorophthalonitrile in the presence of K2CO3 leads to the formation of 4-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile (1), 4-chloro-5-{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy] ethoxy)-phthalonitrile (2), and 4,5-bis{2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy}phthalonitrile (3), respectively. Metal free phthalocyanines were synthesized by tetramerization of the phthalonitriles in 2-(dimethylamino)ethanol while metallophthalocyanines were prepared in the presence of zinc, cobalt or nickel salts. The new compounds were characterized by elemental analysis. IR, H-1, and F-19 NMR and UV-Vis spectroscopy as well as mass spectrometry. The fluoroether substituted Pcs are best soluble in polar solvents such as acetone and THF. Crown Copyright (C) 2012 Published by Elsevier B.V. rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.023

文献信息

• Zn(II) phthalocyanines having fluoroether groups: Synthesis, characterization, photo-physicochemical and biological properties
  作者：Kevser Harmandar、Serpil Gonca、Tuğba Küçük、Aysel Günay、Devrim Atilla、Sadin Özdemir、Ayşe Gül Gürek

  DOI：10.1142/s1088424622501000

  日期：2023.1

  Tetra non-peripheral and peripheral substituted Zn(II) phthalocyanine (Pc) derivatives bearing 2,2-difluoro-2-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy groups (KH-69, KH-71) were synthesized and characterized to be antioxidant and antimicrobial agents. Photo-physicochemical properties of these compounds were investigated. Then, the DPPH free radical scavenging activity of the Pc derivatives was found as 97.74% and 94.89%, respectively. Both the Pc complexes showed perfect DNA nuclease activity with double strain break against pBR 322 plasmid DNA at 100 mg/L concentration. KH-69 and KH-71 indicated good antimicrobial activity against studied Gram-positive and Gram-negative bacteria, and fungal strains. Moreover, the Pcs showed excellent cell viability inhibition activity even at the lowest concentration. These Pc derivatives inhibited P. aeroginasa and S. aureus biofilm formation. The Pcs showed the highest biofilm inhibition with photodynamic therapy against S. aureus and P. aeroginasa with 95.40% and 90.03%, respectively.

  合成了带有 2,2-二氟-2-[1,1,2,2-四氟-2-(三氟甲氧基)乙氧基]乙氧基基团（KH-69、KH-71）的四非外围和外围取代的 Zn(II) 酞菁（Pc）衍生物，并将其表征为抗氧化剂和抗菌剂。研究了这些化合物的光物理化学性质。结果发现，Pc 衍生物的 DPPH 自由基清除活性分别为 97.74% 和 94.89%。在 100 毫克/升浓度下，两种 Pc 复合物对 pBR 322 质粒 DNA 都表现出完美的 DNA 核酸酶活性和双株断裂。KH-69 和 KH-71 对所研究的革兰氏阳性菌、革兰氏阴性菌和真菌菌株具有良好的抗菌活性。此外，即使在最低浓度下，这些 Pc 衍生物也表现出了极佳的细胞活力抑制活性。这些 Pc 衍生物可抑制绿脓杆菌和金黄色葡萄球菌生物膜的形成。光动力疗法对金黄色葡萄球菌和绿脓杆菌的生物膜抑制率最高，分别为 95.40% 和 90.03%。