2,3-dicyanophenyl trifluoromethanesulfonate | 310396-99-7

• 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: 2,3-dicyanophenyl trifluoromethanesulfonate
• 英文别名: Trifluoromethanesulfonic acid 2,3-dicyanophenyl ester；(2,3-dicyanophenyl) trifluoromethanesulfonate
• CAS: 310396-99-7
• 化学式: C₉H₃F₃N₂O₃S
• 分子量: 276.196
• InChiKey: YHHYDZPBBOPWLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-dicyanophenyl trifluoromethanesulfonate 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 作用下， 以 对二甲苯 、 水 、 邻二氯苯 、 甲苯 为溶剂， 反应 22.0h， 生成
  参考文献：
  名称：

  一锅合成π扩展的芴酮键合的亚酞菁

  摘要：

  通过创新的一锅合成法制备了一系列固有的手性非平面芳族发色团，包括带有芴酮融合单元的亚酞菁（SubFcs），该合成依赖于邻苯二甲腈的标准交叉环三聚化反应，然后进行分子内Friedel-Crafts酰化反应。他们的Q波段吸收经历了大约 由于扩大的共轭π系统，每个熔融的芴酮发生20 nm的红移。

  DOI：

  10.1021/acs.orglett.9b00944
• 作为产物：
  描述：

  三氟甲烷磺酰氯 、 2,3-二氰基苯酚 生成 2,3-dicyanophenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Phthalocyanines Obtained from Phthalonitriles with Phenyl Derivatives: A New Method for the Synthesis of the Phthalonitriles by Use of Suzuki-Coupling Reaction

  摘要：

  在苯环上引入四个苯衍生物的酞菁，通过Suzuki-Miyaura偶联反应，从相应的邻苯二腈中制备得到，产率很高。研究发现，酞菁环上的取代基对吸收光谱特性和在氯仿中的溶解度有显著影响。

  DOI：

  10.1246/cl.2000.1200

文献信息

• Synthesis and Characterization of Monoisomeric 1,8,15,22-Substituted (A₃B and A₂B₂) Phthalocyanines and Phthalocyanine−Fullerene Dyads
  作者：Jenni Ranta、Tatu Kumpulainen、Helge Lemmetyinen、Alexander Efimov

  DOI：10.1021/jo100766h

  日期：2010.8.6

  Synthesis and characterization of three phthalocyanine−fullerene (Pc-C60) dyads, corresponding monoisomeric phthalocyanines (Pc), and building blocks, phthalonitriles, are described. Six novel bisaryl phthalonitriles were prepared by the Suzuki−Miyaura coupling reaction from trifluoromethanesulfonic acid 2,3-dicyanophenyl ester and various oxaborolanes. Two phthalonitriles were selected for the synthesis

  描述了三种酞菁-富勒烯（Pc -C 60）二元化合物，相应的单体异构体酞菁（Pc）和结构单元邻苯二甲腈的合成和表征。通过Suzuki-Miyaura偶联反应，由三氟甲磺酸2,3-二氰基苯基酯和各种氧杂硼烷制备了六种新颖的双芳基邻苯二甲腈。选择两种邻苯二甲腈用于合成A 3 B-型和A 2 B 2-型酞菁。邻苯二甲腈4具有庞大的3,5-二-叔-在邻苯二甲酸位置的丁基丁基取代基，仅迫使一种区域异构体形成并大大提高了酞菁的溶解度。邻苯二甲腈8在α位具有3-苯基丙醇侧链，使得可以进一步修饰侧基。合成的单体异构体A 3 B和A 2 B 2型酞菁通过丙二酸残基的连接而被修饰。最后，富勒烯通过一个或两个丙二酸桥与酞菁共价连接，生成Pc -C 60二元组。由于酞菁类化合物的异构体结构和增加的溶解度，化合物的NMR光谱质量得到了显着提高，从而使详细的NMR分析成为可能。合成的二元化合物具有不同的酞菁和富勒烯取
• Metal-Catalyzed Carbon-Fluorine Bond Formation
  申请人：Buchwald Stephen L.

  公开号：US20110015401A1

  公开（公告）日：2011-01-20

  One aspect of the invention relates to a metal-catalyzed conversion of aryl halides and sulfonates to the corresponding aryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of heteroaryl halides and sulfonates to the corresponding heteroaryl fluorides. Another aspect of the invention relates to a metal-catalyzed conversion of vinyl halides and sulfonates to the corresponding vinyl fluorides. In certain embodiments, simple fluoride sources, such as AgF and CsF, are used. In certain embodiments, the transformations tolerate a wide range of functional groups, allowing for introduction of fluorine atoms into highly functionalized organic molecules.

  该发明的一个方面涉及将芳基卤化物和磺酸酯金属催化转化为相应的芳基氟化物。该发明的另一个方面涉及将杂环芳基卤化物和磺酸酯金属催化转化为相应的杂环芳基氟化物。该发明的另一个方面涉及将乙烯卤化物和磺酸酯金属催化转化为相应的乙烯氟化物。在某些实施例中，使用简单的氟化物源，如AgF和CsF。在某些实施例中，这些转化可以容忍各种官能团，从而使高度官能化的有机分子中引入氟原子成为可能。
• Formation and stability of porphyrin and phthalocyanine self-assembled monolayers on ZnO surfaces
  作者：Hanna Hakola、Essi Sariola-Leikas、Paavo Jäntti、Thomas Mokus、Kati Stranius、Alexander Efimov、Nikolai V. Tkachenko

  DOI：10.1142/s1088424616501029

  日期：2016.8

  Formation of self-assembled monolayers (SAMs) of three porphyrin and one phthalocyanine derivatives on thin ZnO film was studied by monitoring absorption spectra of the samples. The compounds were equipped with carboxylic or phosphate groups to bind to the surface. The SAM formation was found to be fast. The layer was formed in less than 15 min for all studied porphyrins, and 30 min was sufficient to form phthalocyanine layer. For porphyrins with different anchor groups the SAM formation was too fast to see any difference between the anchoring groups. The stability of SAMs was tested then by immersing the samples into neat solvents. Upon immersion the SAMs were gradually losing the absorbance for all the compounds with degradation trends being in line with p[Formula: see text] values of the binding groups of the same type. However, even for the weakest binding group the SAM was relatively stable after a few tens of minutes of washing, which was sufficient to remove physisorbed compounds but the SAM was essentially not destroyed. Comparison of SAMs on thin films with SAMs on ZnO nanorods and TiO₂ nanoparticle films indicated the same fast layer formation but relatively weaker SAMs stability, showing 20–40% faster absorption losses during the washing.

  通过监测样品的吸收光谱，研究了三种卟啉和一种酞菁衍生物在氧化锌薄膜上形成自组装单层（SAM）的情况。这些化合物都带有羧基或磷酸基，可与表面结合。研究发现，SAM 的形成速度很快。所有研究的卟啉都在不到 15 分钟的时间内形成了层，而 30 分钟就足以形成酞菁层。对于具有不同锚定基团的卟啉，SAM 的形成速度太快，看不出锚定基团之间有任何区别。然后将样品浸入纯溶剂中测试 SAM 的稳定性。在浸泡过程中，所有化合物的 SAM 吸光度都在逐渐降低，降解趋势与同类结合基团的 p[式：见正文]值一致。不过，即使是结合力最弱的基团，经过几十分钟的洗涤后，SAM 也相对稳定，这足以去除物理吸附的化合物，但 SAM 基本上没有被破坏。将薄膜上的 SAM 与 ZnO 纳米棒和 TiO2 纳米粒子薄膜上的 SAM 进行比较后发现，薄膜上的 SAM 也能快速形成层，但 SAM 的稳定性相对较弱，在洗涤过程中吸收损失的速度要快 20-40%。
• [EN] PHOTOSENSITIZER<br/>[FR] PHOTOSENSIBILISATEUR
  申请人：TTY SAEAETIOE

  公开号：WO2018091774A1

  公开（公告）日：2018-05-24

  The present application relates to a phthalocyanine, to a method for preparing the phthalocyanine, and to an object coated or impregnated with the phthalocyanine. The present application also relates to a method for providing reactive oxygen species, and to a method for disinfecting materials, comprising providing reactive oxygen species to the material to disinfect the material by oxidative action.

  本申请涉及一种酞菁，一种制备酞菁的方法以及涂覆或浸渍酞菁的物体。本申请还涉及一种提供反应性氧化物的方法，以及一种消毒材料的方法，包括通过氧化作用向材料提供反应性氧化物以消毒材料。
• Photodynamic self–disinfecting surface using pyridinium phthalocyanine
  作者：Lijo George、Alexander Müller、Beate Röder、Ville Santala、Alexander Efimov

  DOI：10.1016/j.dyepig.2017.08.021

  日期：2017.12

  We have synthesized novel phthalocyanine with four pyridyl substituents connected to alpha-phthalo-positions via direct C-C bond. The Zn complex and tetracationic derivatives of phthalocyanine were also synthesized and the dyes were impregnated into filter paper to prepare photoactive antimicrobial surface. The photodynamic antimicrobial efficacy of the dyed paper samples was evaluated by a simple and fast setup using bioluminescent microbes. Escherichia coil and Acinetobacter baylyi ADP1 strains carrying bacterial luciferase genes were used in the screening experiment. The most efficient compound, tetra cationic zinc derivative 8, was investigated further. The compound was highly water soluble, had high molar absorptivity and exhibited good adhesion to the filter paper without leaching into the solution. The singlet oxygen quantum yield of tetracationic zinc derivative 8 in water was found out to be 30 +/- 20%. According to the cell viability assay test performed on E. coli wild type in solution, the molecule had similar or better photo toxicity as the reference photosensitizer, tetrakis (1-methyl-pyridinium-4-yl) porphyrin (TMPyP). Antimicrobial efficacy of the dye 8 on photoactive surface was studied by live cell assessment through colony forming unit (CFU) counting. The colored surface demonstrated 3 log reduction in CFU against E. coli and A. baylyi ADP1 just after 1 h of illumination with the white light of low intensity. (C) 2017 Elsevier Ltd. All rights reserved.