2-(2,4-difluorophenyl)-5-dimethylamino-pyridine | 934477-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2,4-difluorophenyl)-5-dimethylamino-pyridine
• 英文别名: 6-(2,4-difluorophenyl)-N,N-dimethylpyridin-3-amine
• CAS: 934477-86-8
• 化学式: C₁₃H₁₂F₂N₂
• 分子量: 234.248
• InChiKey: QOWVTVSZBKRLKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iridium(III) chloride trihydrate 、 2-(2,4-difluorophenyl)-5-dimethylamino-pyridine 以 乙二醇甲醚 、 水 为溶剂， 生成
  参考文献：
  名称：

  A Semi‐Automated, High‐Throughput Approach for the Synthesis and Identification of Highly Photo‐Cytotoxic Iridium Complexes

  摘要：

  The discovery of new compounds with pharmacological properties is usually a lengthy, laborious and expensive process. Thus, there is increasing interest in developing workflows that allow for the rapid synthesis and evaluation of libraries of compounds with the aim of identifying leads for further drug development. Herein, we apply combinatorial synthesis to build a library of 90 iridium(III) complexes (81 of which are new) over two synthesise‐and‐test cycles, with the aim of identifying potential agents for photodynamic therapy. We demonstrate the power of this approach by identifying highly active complexes that are well‐tolerated in the dark but display very low nM phototoxicity against cancer cells. To build a detailed structure–activity relationship for this class of compounds we have used density functional theory (DFT) calculations to determine some key electronic parameters and study correlations with the experimental data. Finally, we present an optimised semi‐automated synthesise‐and‐test protocol to obtain multiplex data within 72 hours.

  DOI：

  10.1002/anie.202401808
• 作为产物：
  描述：

  6-溴-N,N-二甲基吡啶-3-胺 、 2,4-二氟苯硼酸 在 Pd(PPh3)4 potassium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 以3 g (80%)的产率得到2-(2,4-difluorophenyl)-5-dimethylamino-pyridine
  参考文献：
  名称：

  Light-Emitting Material

  摘要：

  这项发明涉及包含新型正金属化过渡金属配合物[ĈN]2ML的发光材料，包括螯合单离子配体（L），也称为辅助配体。令人惊讶地发现，当辅助配体包含带有足够电子给体性质的取代芳香环的取代基时，所述配体（L）有利地参与发射过程，显著将发射转移到更高能量（蓝移），并能够显著改善配合物[ĈN]2ML的发射效率。本发明还涉及使用所述发光材料和包括所述发光材料的有机发光器件。

  公开号：

  US20090200920A1

文献信息

• LIGHT-EMITTING MATERIAL
  申请人：Solvay SA

  公开号：EP1934302A2

  公开（公告）日：2008-06-25
• [EN] LIGHT-EMITTING MATERIAL<br/>[FR] MATERIAU ELECTROLUMINESCENT
  申请人：SOLVAY

  公开号：WO2007042474A2

  公开（公告）日：2007-04-19

  [EN] This invention pertains to light emitting materials comprising novel ortho-metalated transition metal complexes [C^N]2ML, comprising chelate monoionic ligands (L), also called ancillary ligands. It has been surprisingly found that when the ancillary ligand comprises a substituted aromatic ring bearing a substituent possessing adequate electron-donating properties, said ligand (L) advantageously participates in the emission process, significantly shifting emission towards higher energies (blue-shift) and enabling appreciable improvement of the emission efficiency of complexes [C^N]2ML. Still objects of the invention are the use of said light emitting materials and organic light emitting device comprising said light emitting material.
  [FR] La présente invention concerne de nouveaux matériaux électroluminescents comprenant des complexes à base de métaux de transition ortho-métalatés [C^N]2ML, comportant des ligands à ions uniques chélatés (L), également appelés des ligands auxiliaires. Chose étonnante, il s'est avéré que lorsque le ligand auxiliaire comprend un cycle aromatique substitué comportant un substituant possédant des propriétés donneuses d'électrons adéquates, ledit ligand (L) participe avantageusement au processus d'émission, déplaçant sensiblement les émissions vers des énergies supérieures (déplacement hypsochrome) et permettant d'obtenir des améliorations appréciables au niveau du rendement d'émission des complexes [C^N]2ML. L'invention concerne également l'utilisation desdits matériaux électroluminescents et des dispositifs électroluminescents organiques comprenant ce matériau électroluminescent.
• Light-Emitting Material
  申请人：Jin Sung Ho

  公开号：US20090200920A1

  公开（公告）日：2009-08-13

  This invention pertains to light emitting materials comprising novel ortho-metalated transition metal complexes [ĈN] 2 ML, comprising chelate monoionic ligands (L), also called ancillary ligands. It has been surprisingly found that when the ancillary ligand comprises a substituted aromatic ring bearing a substituent possessing adequate electron-donating properties, said ligand (L) advantageously participates in the emission process, significantly shifting emission towards higher energies (blue-shift) and enabling appreciable improvement of the emission efficiency of complexes [ĈN] 2 ML. Still objects of the invention are the use of said light emitting materials and organic light emitting device comprising said light emitting material.

  这项发明涉及包含新型正金属化过渡金属配合物[ĈN]2ML的发光材料，包括螯合单离子配体（L），也称为辅助配体。令人惊讶地发现，当辅助配体包含带有足够电子给体性质的取代芳香环的取代基时，所述配体（L）有利地参与发射过程，显著将发射转移到更高能量（蓝移），并能够显著改善配合物[ĈN]2ML的发射效率。本发明还涉及使用所述发光材料和包括所述发光材料的有机发光器件。
• A Semi‐Automated, High‐Throughput Approach for the Synthesis and Identification of Highly Photo‐Cytotoxic Iridium Complexes
  作者：Timothy Kench、Arielle Rahardjo、Gianmarco G. Terrones、Adinarayana Bellamkonda、Thomas E. Maher、Marko Storch、Heather J. Kulik、Ramon Vilar

  DOI：10.1002/anie.202401808

  日期：2024.4.24

  The discovery of new compounds with pharmacological properties is usually a lengthy, laborious and expensive process. Thus, there is increasing interest in developing workflows that allow for the rapid synthesis and evaluation of libraries of compounds with the aim of identifying leads for further drug development. Herein, we apply combinatorial synthesis to build a library of 90 iridium(III) complexes (81 of which are new) over two synthesise‐and‐test cycles, with the aim of identifying potential agents for photodynamic therapy. We demonstrate the power of this approach by identifying highly active complexes that are well‐tolerated in the dark but display very low nM phototoxicity against cancer cells. To build a detailed structure–activity relationship for this class of compounds we have used density functional theory (DFT) calculations to determine some key electronic parameters and study correlations with the experimental data. Finally, we present an optimised semi‐automated synthesise‐and‐test protocol to obtain multiplex data within 72 hours.