(Z)-1-(4-bromophenyl)-3-(phenylamino)prop-2-en-1-one

• 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: (Z)-1-(4-bromophenyl)-3-(phenylamino)prop-2-en-1-one
• 英文别名: (Z)-1-(4-bromophenyl)-3-(anilino)prop-2-en-1-one；(Z)-3-anilino-1-(4-bromophenyl)prop-2-en-1-one
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: RNSSCYNXZVOAEI-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9,9-二甲基吖啶 、 (Z)-1-(4-bromophenyl)-3-(phenylamino)prop-2-en-1-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以75%的产率得到
  参考文献：
  名称：

  Orange-red thermally activated delay fluorescence emitters based on asymmetric difluoroboron chelated enaminone: Impact of donor position on luminescent properties

  摘要：

  Asymmetric enaminone difluoroboron complexes (BFs) exhibit highly solid emission and appropriated electron-accepting properties, whereas the position of the substituents has a significant influence on their optical properties due to the structural asymmetry. In this work, we employed BF as acceptor and 9,9-dimethylacridine (DMAC) as donor to construct two thermally activated delay fluorescence (TADF) molecules DMAC-BF and BF-DMAC, in which DMAC unit was set on the B-O and B-N sides of BF, respectively. DMAC-BF and BF-DMAC exhibited the broad orange-red emission bands in toluene, while they emitted yellow and red fluorescence in solid state, respectively. The photoluminescence quantum yield (PLOY) of DMAC-BF (52%) is higher than that of BF-DMAC (29%), owing to its lower nonradiative decay rate. Solution-processed organic light-emitting diode (OLED) devices based on both of DMAC-BF and BF-DMAC exhibited orange-red electroluminicence spectra. Owing to its higher photoluminescence quantum yield, DMAC-BF-based OLED exhibited better electroluminicence performance with a maximum current efficiency of 24.9 cd/A, a maximum power efficiency of 23.0 lm/W, and a maximum EQE of 11.3%.

  DOI：

  10.1016/j.dyepig.2020.108810
• 作为产物：
  描述：

  1-[(E)-3-(4-bromophenyl)-3-oxoprop-1-en-1-yl]pyridinium bromide 、 N,N'-二苯基硫脲 以 乙腈 为溶剂， 以40%的产率得到
  参考文献：
  名称：

  Features of reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with binucleophiles

  摘要：

  Regardless of pH and a solvent nature the reactions of (E)-1-(beta-aroylvinyl)pyridinium bromides with hydrazine led to the formation of pyrazole derivatives. The salts reacted with thiourea via intermediate formation of 4-arylpyrimidine-2-thiol to give (Z)-2-[(beta-aroylvinyl)sulfanyl]-4-arylpyrimidines. In the case of N,N'-diphenylthiourea the reaction provided 6-aryl-3-aroyl-1-phenylpyridinium bromides. Pyridine hydrobromide liberated in the reaction course has a major influence on the process chemoselectivity.

  DOI：

  10.1134/s1070363216070070

文献信息

• Palladium-Catalyzed Intermolecular Oxidative Coupling Reactions of (<i>Z</i>)-Enamines with Isocyanides through Selective β-C(sp²)-H and/or C=C Bond Cleavage
  作者：Weigao Hu、Jia Zheng、Meng Li、Wanqing Wu、Haiyang Liu、Huanfeng Jiang

  DOI：10.1002/cjoc.201800127

  日期：2018.8

  two efficient palladium‐catalyzed intermolecular oxidative coupling reactions of (Z)‐enamines with isocyanides via selective β‐C(sp2)‐H and/or C=C bond cleavage have been developed, leading to controllable chemodivergent and stereoselective construction of a wide range of (E)‐β‐carbamoylenamine derivatives containing strong intramolecular hydrogen bonds. Furthermore, possible reaction pathways for these

  本文中，已开发出两种有效的钯催化（Z）-烯胺与异氰酸酯通过选择性β-C（sp 2）-H和/或C = C键裂解的分子间氧化偶联反应，从而导致可控的化学扩散和立体选择性结构多种包含强分子内氢键的（E）-β-氨基甲酰亚胺衍生物。此外，在初步机理研究的基础上，提出了这些转化的可能反应途径。
• CN114853792
  申请人：——

  公开号：——

  公开（公告）日：——
• Orange-red thermally activated delay fluorescence emitters based on asymmetric difluoroboron chelated enaminone: Impact of donor position on luminescent properties
  作者：Hua Li、Haiyang Shu、Xin Wang、Xiaofu Wu、Hongkun Tian、Hui Tong、Lixiang Wang

  DOI：10.1016/j.dyepig.2020.108810

  日期：2021.1

  Asymmetric enaminone difluoroboron complexes (BFs) exhibit highly solid emission and appropriated electron-accepting properties, whereas the position of the substituents has a significant influence on their optical properties due to the structural asymmetry. In this work, we employed BF as acceptor and 9,9-dimethylacridine (DMAC) as donor to construct two thermally activated delay fluorescence (TADF) molecules DMAC-BF and BF-DMAC, in which DMAC unit was set on the B-O and B-N sides of BF, respectively. DMAC-BF and BF-DMAC exhibited the broad orange-red emission bands in toluene, while they emitted yellow and red fluorescence in solid state, respectively. The photoluminescence quantum yield (PLOY) of DMAC-BF (52%) is higher than that of BF-DMAC (29%), owing to its lower nonradiative decay rate. Solution-processed organic light-emitting diode (OLED) devices based on both of DMAC-BF and BF-DMAC exhibited orange-red electroluminicence spectra. Owing to its higher photoluminescence quantum yield, DMAC-BF-based OLED exhibited better electroluminicence performance with a maximum current efficiency of 24.9 cd/A, a maximum power efficiency of 23.0 lm/W, and a maximum EQE of 11.3%.
• Features of reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with binucleophiles
  作者：R. Dzh. Khachikyan、Z. G. Ovakimyan、G. A. Panosyan、R. A. Tamazyan、A. G. Ayvazyan

  DOI：10.1134/s1070363216070070

  日期：2016.7

  Regardless of pH and a solvent nature the reactions of (E)-1-(beta-aroylvinyl)pyridinium bromides with hydrazine led to the formation of pyrazole derivatives. The salts reacted with thiourea via intermediate formation of 4-arylpyrimidine-2-thiol to give (Z)-2-[(beta-aroylvinyl)sulfanyl]-4-arylpyrimidines. In the case of N,N'-diphenylthiourea the reaction provided 6-aryl-3-aroyl-1-phenylpyridinium bromides. Pyridine hydrobromide liberated in the reaction course has a major influence on the process chemoselectivity.