4,6-bis(4-bromophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile | 888629-72-9

• 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: 4,6-bis(4-bromophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile
• 英文别名: MAP Kinase Inhibitor, 14；4,6-bis(4-bromophenyl)-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 888629-72-9
• 化学式: C₁₈H₁₀Br₂N₂O
• 分子量: 430.098
• InChiKey: MTDHJTKCWYVKGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-bis(4-bromophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile 在 三氯氧磷 作用下， 生成
  参考文献：
  名称：

  Multi-targeted anti-Alzheimer's agents: Synthesis, biological evaluation, and molecular modeling study of some pyrazolopyridine hybrids

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115880
• 作为产物：
  描述：

  4-溴苯乙酮 、 对溴苯甲醛 、 氰乙酸乙酯 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以70%的产率得到4,6-bis(4-bromophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  基于苯并噻二唑和氰基吡啶受体部分的π共轭共聚物以及其他π桥单元的合成，光物理和理论研究

  摘要：

  通过基于苯并噻二唑和氰基吡啶部分以及其他π桥单元（噻吩和/或苯）的Pd催化交叉偶联合成了一组π共轭共聚物。它们的化学结构已通过各种分析技术（元素，IR，1 H和131 H NMR分析。所有共聚物在大多数常见有机溶剂中均显示出良好的溶解性。热重分析（TGA）分析表明它们具有良好的热稳定性，在高达260°C的温度下没有明显的重量损失。估计的薄膜光学带隙在2.25–2.62 eV的范围内。发现π桥单元（苯和/或噻吩）显着影响共聚物的分子结构和光电性能。它们在稀释溶液中显示出良好的荧光，其中通过在526.0–532.0 nm范围内的波长进行辐射激发获得荧光发射光谱。X射线衍射（XRD）显示，所有共聚物在2θ= 22.5–23处均显示对称的卤素峰。8°对应于烷基侧链的存在，此外在〜2°处的2θ处有一个小的强度峰，这表明薄膜中存在一定程度的残留物，在某些范围内具有结晶性。密度泛函理论（DFT）和随时间

  DOI：

  10.1002/poc.4158

文献信息

• New cyanopyridine based conjugated polymers carrying auxiliary electron donors: From molecular design to blue emissive PLEDs
  作者：Naveenchandra Pilicode、Praveen Naik、K.M. Nimith、Madhukara Acharya、M.N. Satyanarayan、Airody Vasudeva Adhikari

  DOI：10.1016/j.dyepig.2019.108046

  日期：2020.3

  respectively as determined by GPC technique. Furthermore, the new polymers PPy1-3, were shown to be stable thermally up to 308–347 °C. Evidently, they exhibited good photophysical behavior with their optical energy band gaps of 2.53–2.63 eV. Finally, the polymers PPy1-3 were employed as an active emissive layer in standard ITO/PEDOT:PSS/Polymer/Al configured PLEDs. Interestingly, at 12 V all the newly

  三个新的DA（受主-受体）配置的共轭聚合物，即 PPy 1-3，以带有各种辅助供体的强电子接受性氰基吡啶骨架为中心。亚苯基（PPy 1），联苯（PPy 2）和芴（PPy 3）被设计并合成为PLED的蓝色发射器。对新聚合物进行了光谱，热，光物理和电化学表征。同样，使用Turbomole 7.2 V软件包在B3LYP / TZVP混合水平上对聚合物的重复单元进行了计算研究（DFT）。此外，通过GPC技术测定，发现它们的重均分子量分别为38.8kDA，38.9kDA和57.7kDA。此外，新型聚合物PPy 1-3在高达308–347°C的温度下也显示出稳定的热稳定性。显然，它们表现出良好的光物理行为，其光能带隙为2.53–2.63 eV。最后，聚合物PPy 1-3在标准ITO / PEDOT：PSS /聚合物/ Al构造的PLED中用作有源发射层。有趣的是，所有新制造的器件都在12 V电压下表现
• Synthesis, characterization and electroluminescence studies of cyanopyridine-based π-conjugative polymers carrying benzo[<i>c</i>][1,2,5]thiadiazole and naphtho[1,2-<i>c</i>:5,6-<i>c</i>′]bis([1,2,5]thiadiazole) units
  作者：Naveenchandra Pilicode、Praveen Naik、Madhukara Acharya、Airody Vasudeva Adhikari

  DOI：10.1039/d0nj02141e

  日期：——

  Four new cyanopyridine based polymers, i.e.TDPy1-4 were designed, synthesized and well-characterized. The detailed studies reveal that the polymers own all the prerequisites required for the PLED application as active green light emitters.

  基于四种新的氰基吡啶聚合物，即TDPy1-4，进行了设计、合成和充分表征。详细研究表明，这些聚合物具有作为主动绿光发射体在PLED应用中所需的所有先决条件。
• One-Pot Synthesis of 4,6-Diaryl-2-oxo(imino)-1,2-dihydropyridine-3-carbonitrile; a New Scaffold for p38α MAP Kinase Inhibition
  作者：Aya M. Serry、Sabine Luik、Stefan Laufer、Ashraf H. Abadi

  DOI：10.1021/cc1000488

  日期：2010.7.12

  multicomponent reaction of the appropriate acetophenone, aromatic aldehyde, ammonium acetate, and malononitrile or ethyl cyanoacetate. The products were obtained with excellent yields. The prepared compounds were evaluated for their in vitro ability to inhibit p38 alpha-MAP kinase. Several compounds showed p38 MAP kinase inhibitory properties with IC(50) as low as 0.07 microM. This is the first time to report

  通过适当的苯乙酮，芳香醛，铵的多组分反应，合成了两类通式为4,6-二芳基-2-氧代-1,2-二氢吡啶-3-腈的新化合物及其等规2-亚氨基衍生物。乙酸，丙二腈或氰基乙酸乙酯。获得的产物具有优异的产率。评价制备的化合物的体外抑制p38α-MAP激酶的能力。几种化合物显示p38 MAP激酶抑制特性，IC（50）低至0.07 microM。这是首次报道具有支架的化合物，例如p38α-MAP激酶抑制剂。这证明了在药物发现中多组分反应的潜力。
• New blue emissive conjugated small molecules with low lying HOMO energy levels for optoelectronic applications
  作者：C. Trupthi Devaiah、B. Hemavathi、T.N. Ahipa

  DOI：10.1016/j.saa.2016.12.035

  日期：2017.3

  of the solvent greatly influenced the spectra. The electrochemical studies were carried out using cyclic voltammetry to calculate the HOMO-LUMO energy levels. The study revealed that the synthesized conjugated small molecules possess low lying HOMO energy levels which can be exploited for application in various fields of optoelectronics.

  已经设计，开发和表征了具有氰基吡啶酮核心（CP1-5）的多功能共轭小分子，该分子由位置-4和-6处的各种供体/受体部分组成。他们的溶剂变色研究是使用Lippert-Mataga，Kamlet-Taft和加泰罗尼亚溶剂规模进行的，并进行了分析，并获得了有趣的结果。溶剂的极化率/双极性极大地影响了光谱。使用循环伏安法进行电化学研究，以计算HOMO-LUMO的能级。研究表明，合成的共轭小分子具有较低的HOMO能级，可用于光电子学的各个领域。
• Cyanopyridine based conjugated polymer-synthesis and characterization
  作者：B. Hemavathi、T.N. Ahipa、Saju Pillai、Ranjith Krishna Pai

  DOI：10.1016/j.polymer.2015.09.053

  日期：2015.11

  Two novel D-A polymers containing pyridine with vinylene spacer, P1 and P2 were synthesised through Heck polymerisation. In both the polymers, pyridine is linked with two donor phenylene at position-4 and -6, and electron withdrawing cyano group at position-3. Additionally, P1 possess methoxy side chain at position-2 of 3-cyanopyridine and P2 is flanked with both methoxy and octyloxy side chain at alternate pyridine. The polymers are well characterised with H-1-NMR, UV-Vis absorption, PL, GPC, TGA, cyclic voltammetry and AFM. TGA data reveal that the polymers P1 and P2 are thermally stable up to 350-400 degrees C. The UV-Vis absorption spectra for solid thin films envisage efficient molecular stacking with red shifting the absorption maxima to 30 nm when compared to solution. The obtained polymers have a band gap of 1.8-1.93 eV with low laying HOMO and LUMO energy level. The polymers displayed very good blue fluorescence in CHCl3 upon irradiated with UV light (254 nm) and Atomic force microscopy (AFM) applications to polymer P1 and P2 surfaces are providing interesting images of nanometre-scale polymer structures. (C) 2015 Elsevier Ltd. All rights reserved.