1-(6,8-dibromo-2-methyl-3-quinolinyl)ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(6,8-dibromo-2-methyl-3-quinolinyl)ethanone
• 英文别名: 1-(6,8-dibromo-2-methylquinolin-3-yl)ethanone；3-acetyl-6,8-dibromo-2-methylquinoline
• 化学式: C₁₂H₉Br₂NO
• 分子量: 343.018
• InChiKey: JRPISLSOTABNNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(6,8-dibromo-2-methyl-3-quinolinyl)ethanone 、 二茂铁甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.32h， 以90%的产率得到ferrocenyl-1-(6,8-dibromo-2-methylquinolin-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  The facile and efficient ultrasound-assisted synthesis of new quinoline-appended ferrocenyl chalcones and their properties

  摘要：

  The facile and efficient synthesis of quinoline-appended ferrocenyl chalcones via the condensation of acetylferrocene (or substituted 2-methyl-3-acetylquinoline) with 2-chloro-3-formylquinoline (or ferrocenecarboxaldehyde) in ethanol under basic conditions by the ultrasonic method is reported and compared to the results of synthesis achieved through conventional methods. Two derivatives were investigated crystallographically which confirmed the E-conformation about the C=C ethylene bond in each case. Redox chemistry of the new chalcones was investigated by cyclic voltammetry which showed quasi-reversible one-electron redox processed with potentials correlated with electron-withdrawing substituents. The compounds showed promising antimicrobial properties, with derivatives 3a and 6a showing the maximum activity against bacterial and fungal strains, respectively. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.12.022
• 作为产物：
  描述：

  2-氨基-3,5-二溴苯甲醛 、 乙酰丙酮 在 metal organic framework of 1,3-bis(carboxymethyl)imidazolium calcium-1 complex 作用下， 以 neat (no solvent) 为溶剂， 反应 1.5h， 以99%的产率得到1-(6,8-dibromo-2-methyl-3-quinolinyl)ethanone
  参考文献：
  名称：

  喹啉合成中的多功能钡和咪唑二羧酸钙非均相催化剂

  摘要：

  已经从容易获得的有机连接基和金属源以直接的方式制备了多种基于钙和钡的非均相催化剂。这组材料构成了用于有机转化的有价值的催化剂阵列，从而开拓了它们的实际用途。

  DOI：

  10.1002/ejoc.201700990

文献信息

• Rapid and efficient synthesis of poly-substituted quinolines assisted by p-toluene sulphonic acid under solvent-free conditions: comparative study of microwave irradiation versus conventional heating
  作者：Cheng-Sheng Jia、Ze Zhang、Shu-Jiang Tu、Guan-Wu Wang

  DOI：10.1039/b513721g

  日期：——

  A rapid and efficient method for the preparation of various poly-substituted quinolines has been developed through the Friedlander condensation of 2-aminoarylketone or 2-aminoarylaldehyde with carbonyl compounds in the presence of p-toluene sulphonic acid, which was achieved by both microwave irradiation and conventional heating under solvent-free conditions.

  在对甲苯磺酸的存在下，通过2-氨基芳基酮或2-氨基芳基醛与羰基化合物的弗里德兰德缩合反应，已经开发出一种快速有效的制备各种多取代喹啉的方法，该方法通过微波辐射和微波辐射来实现。在无溶剂条件下进行常规加热。
• Design, Synthesis, Physicochemical Studies, Solvation, and DNA Damage of Quinoline-Appended Chalcone Derivative: Comprehensive Spectroscopic Approach toward Drug Discovery
  作者：Himank Kumar、Anjan Chattopadhyay、R. Prasath、Vinod Devaraji、Ritika Joshi、P. Bhavana、Praveen Saini、Sujit Kumar Ghosh

  DOI：10.1021/jp5025262

  日期：2014.7.3

  transfer (TICT) excited state. The radiationless deactivation of the TICT state is found to be promoted strongly by hydrogen bonding. Quantum mechanical (DFT, TDDFT, and ZINDO–CI) calculations show that the ADMQ is sort of molecular rotor which undergoes intramolecular twist followed by a complete charge transfer in the optimized excited state. FTIR studies reveals that ADMQ undergoes important structural

  本研究概括了潜在的抗肿瘤，抗癌喹啉附加查尔酮衍生物（E的设计，合成，光物理，溶剂化以及与小牛胸腺DNA的相互作用）-3-（蒽-10-基）-1-（6,8-二溴-2-甲基喹啉-3-基）丙-2-烯-1-酮（ADMQ）使用稳态吸收和荧光光谱法，分子建模，分子对接，傅立叶变换红外光谱（FTIR），分子动力学（MD）模拟和凝胶电泳研究。ADMQ在多种不同极性的溶剂中显示出异常的光物理行为。已经观察到双重发射以及扭曲的分子内电荷转移（TICT）激发态的形成。发现通过氢键强烈促进了TICT状态的无辐射失活。量子力学（DFT，TDDFT和ZINDO-CI）计算表明，ADMQ是一种分子转子，它经历分子内扭曲，然后在最佳激发态下完成电荷转移。FTIR研究表明，在生理pH值下，ADMQ从其天然结构到β-羟基酮的形式发生了重要的结构变化。在琼脂糖凝胶DNA电泳实验中已鉴定出浓度依赖性的DNA裂解，并得到了MD模拟的
• Achieving the Reverse Intersystem Crossing in Chalcone Based Donor‐Acceptor System through Down‐Conversion of Triplet Exciton
  作者：Piyush Singh、Pradip Pattanayak、Pradipta Purkayastha、Sujit Kumar Ghosh

  DOI：10.1002/chem.202302587

  日期：2023.11.16

  In recent years, understanding the mechanism of thermally activated delayed fluorescence (TADF) has become the primary choice for designing high‐efficiency, low‐cost, metal‐free organic light emitting diodes (OLEDs). Herein, we propose a strategically designed chalcone based donor‐acceptor system, where intensification of delayed fluorescence with decrease in temperature (300 K to 100 K) is observed; the theoretical investigations of electronic states and orbital characters uncovered a new cold rISC pathway in donor‐acceptor system, where rISC occurs through the down‐conversation of higher triplet exciton (from T₃) to lowest singlet state (S₁), having negative energy splitting, thus no thermal energy is required. The comprehensive research described herein might open‐up new avenues in donor‐acceptor system over the conventional up‐convention of triplet exciton and demonstrates that not necessarily all delayed fluorescence are thermally activated (TADF).

  摘要 近年来，了解热激活延迟荧光（TADF）的机理已成为设计高效、低成本、无金属有机发光二极管（OLED）的首要选择。在本文中，我们提出了一种基于查尔酮的供体-受体系统的战略设计，在该系统中，延迟荧光随着温度的降低（从 300 K 到 100 K）而增强；对电子状态和轨道特性的理论研究发现了供体-受体系统中一种新的冷rISC途径，rISC是通过较高的三重态激子（从T3）向最低的单重态（S1）的下转换而发生的，具有负能量分裂，因此不需要热能。本文所述的综合研究可能会为供体-受体系统开辟新的途径，而不是传统的三重激子向上转换，并证明并非所有延迟荧光都是热激活的（TADF）。
• Benign and highly efficient synthesis of quinolines from 2-aminoarylketone or 2-aminoarylaldehyde and carbonyl compounds mediated by hydrochloric acid in water
  作者：Guan-Wu Wang、Cheng-Sheng Jia、Ya-Wei Dong

  DOI：10.1016/j.tetlet.2005.12.053

  日期：2006.2

  An environmentally friendly and highly efficient procedure for the preparation Of substituted quinoline derivatives was developed by a simple Friedlander reaction of 2-aminoarylketone or 2-aminoarylaldehyde with carbonyl compounds in the presence of hydrochloric acid utilizing water as the solvent. (c) 2005 Elsevier Ltd. All rights reserved.
• Efficient ultrasound-assisted synthesis, spectroscopic, crystallographic and biological investigations of pyrazole-appended quinolinyl chalcones
  作者：R. Prasath、P. Bhavana、S. Sarveswari、Seik Weng Ng、Edward R.T. Tiekink

  DOI：10.1016/j.molstruc.2014.10.026

  日期：2015.2

  Two series of new quinolinyl chalcones containing a pyrazole group, 3a-f and 4a-r, have been synthesized by Claisen-Schmidt condensation of the derivatives of 2-methyl-3-acetylquinoline with either substituted 1,3-diphenyl-1H-pyrazole-4-carbaldehyde or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde in 76-93% yield under ultrasonic method. The compounds were characterized using IR, H-1 NMR and ESI-MS spectroscopic methods and, for representative compounds, by X-ray crystallography. An E-configuration about the C=C ethylene bond has been established via H-1 NMR spectroscopy and X-ray crystallography. These compounds show promising anti-microbial properties, with 4a and 3e being the most potent against bacterial and fungal strains, respectively and the methoxy substituted compounds showed moderate anti-oxidant activity. (C) 2014 Elsevier B.V. All rights reserved.