2,2'-dicarboxyltriphenylamine | 109747-49-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2'-dicarboxyltriphenylamine
• 英文别名: 2,2'-phenylimino-di-benzoic acid；2,2'-Phenylimino-di-benzoesaeure；(Phenylazanediyl)dibenzoic acid；2-(N-(2-carboxyphenyl)anilino)benzoic acid
• CAS: 109747-49-1
• 化学式: C₂₀H₁₅NO₄
• 分子量: 333.343
• InChiKey: LNNCMZGYQPGZMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  542.3±35.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2'-dicarboxyltriphenylamine 在 aluminum (III) chloride 、 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以73 %的产率得到5H,9H-Chino<3,2,1-de>acridin-5,9-dion
  参考文献：
  名称：

  Red-Shifted Emission in Multiple Resonance Thermally Activated Delayed Fluorescent Materials through Malononitrile Incorporation

  摘要：

  DOI：

  10.1021/acs.orglett.3c02858
• 作为产物：
  描述：

  2-碘苯甲酸甲酯 在 copper(l) iodide 、 铜 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 二丁醚 为溶剂， 反应 48.0h， 生成 2,2'-dicarboxyltriphenylamine
  参考文献：
  名称：

  Helix versus zig-zag: control of supramolecular topology via carboxylic acid conformations in ortho-substituted phenyl amines

  摘要：

  邻位取代的苯胺形成超分子螺旋或之字形结构，具体取决于羧酸取代基的构象——这可以通过分子内氢键相互作用来控制。

  DOI：

  10.1039/b110049a

文献信息

• Efficient enantioselective fluorination of β-keto esters/amides catalysed by diphenylamine-linked bis(thiazoline)–Cu(OTf)₂complexes
  作者：Jiahuan Peng、Da-Ming Du

  DOI：10.1039/c3ra45438j

  日期：——

  An efficient highly enantioselective fluorination of β-keto esters/amides catalysed by diphenylamine-linked bis(thiazoline)–Cu(OTf)2 complexes has been developed. The corresponding products could be obtained with good to excellent enantioselectivities (up to > 99% ee) in excellent yields by utilizing N-fluorobisbenzenesulphonimide (NFSI) as fluorination reagent.

  已经开发了一种有效的高对映选择性氟化的二苯胺连接的双（噻唑啉）-Cu（OTf）2配合物催化的β-酮酯/酰胺。通过使用N-氟代双苯磺酰亚胺（NFSI）作为氟化试剂，可以以优异的收率获得具有良好至优异的对映选择性（最高> 99％ee）的相应产物。
• Helix versus zig-zag: control of supramolecular topology via carboxylic acid conformations in ortho-substituted phenyl amines
  作者：Jason E. Field、D. Venkataraman

  DOI：10.1039/b110049a

  日期：2002.2.12

  ortho-Substituted phenyl amines form supramolecular helices or zig-zag structures, depending on the conformation of the carboxylic acid substituents — which can be controlled by an intramolecular hydrogen-bonding interaction.

  邻位取代的苯胺形成超分子螺旋或之字形结构，具体取决于羧酸取代基的构象——这可以通过分子内氢键相互作用来控制。
• Compounds for organic electronic devices
  申请人：Parham Amir

  公开号：US20090295275A1

  公开（公告）日：2009-12-03

  The present invention relates to the improvement of organic electroluminescent devices, in particular blue-emitting devices, by using compounds of the formula (1) or formula (2) as dopants in the emitting layer or as hole-transport material in a hole-transport layer.

  本发明涉及使用公式（1）或公式（2）的化合物作为发射层中的掺杂剂或在空穴传输层中作为空穴传输材料，以改进有机电致发光装置，特别是蓝色发光装置。
• Convergent synthesis of triarylamines <i>via</i> Ni-catalyzed dual C(sp²)–H amination from benzamides with benzohydroxamic acids
  作者：Wenwei Li、Ruxue Wang、Zhefeng Li、Jiuxi Chen、Yuhong Zhang、Ningning Lv

  DOI：10.1039/d3cc00165b

  日期：——

  An unprecedented method of nickel-catalyzed dual C(sp2)–H amination of N-quinolylbenzamides with benzohydroxamic acids is developed to access triarylamines in one pot. For the first time, broad-spectrum hydroxylamine is employed as an amino source for C–H amination, featuring good chemo-selectivity and functional group tolerance. Furthermore, the catalytic system could be further extended to N-(pivaloyloxy)benzamide

  开发了一种前所未有的镍催化双 C(sp 2 )–H 胺化N-喹啉基苯甲酰胺与苯甲氧肟酸的方法，可在一锅中获得三芳基胺。首次将广谱羟胺用作C-H胺化的氨基源，具有良好的化学选择性和官能团耐受性。此外，该催化体系可以进一步扩展到N- (新戊酰氧基)苯甲酰胺、二恶唑酮、异氰酸酯和苯胺，用于 C-H 胺化。
• Cobalt-Catalyzed Oxidative C–H/N–H Cross-Coupling: Selective and Facile Access to Triarylamines
  作者：Cong Du、Peng-Xiang Li、Xinju Zhu、Jiao-Na Han、Jun-Long Niu、Mao-Ping Song

  DOI：10.1021/acscatal.7b00262

  日期：2017.4.7

  As a powerful synthetic tool for the formation of aromatic C-N bonds, the reported transition-metal-catalyzed direct C-H amination has been ineffective for the synthesis of triarylamines for a long time. Herein, an elegant strategy for the preparation of triarylamines was disclosed using inexpensive Co(OAc)(2)center dot 4H(2)O as the catalyst. It is noteworthy that unactivated arenes and simple anilines were employed as the starting materials with good functional group tolerance. In addition, an organometallic Co(III) species was isolated and identified by X-ray crystallography, thus providing some in-depth insights into the mechanism.