(6-bromoquinolin-3-yl)(phenyl)methanone | 1266247-70-4

• 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: (6-bromoquinolin-3-yl)(phenyl)methanone
• 英文别名: (6-Bromoquinolin-3-yl)-phenylmethanone
• CAS: 1266247-70-4
• 化学式: C₁₆H₁₀BrNO
• 分子量: 312.166
• InChiKey: DPPNXWIAIUTBMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基-5-溴苯甲醛 、 1-苯基-2-丙炔-1-酮 在 iron(III) chloride hexahydrate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以76%的产率得到(6-bromoquinolin-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Iron-catalyzed cascade reaction of ynone with o-aminoaryl compounds: a Michael addition–cyclization approach to 3-carbonyl quinolines

  摘要：

  An efficient iron-catalyzed cascade Michael addition-cyclization of o-aminoaryl compounds including o-aminoaryl aldehydes, o-aminoaryl ketones, and o-aminobenzyl alcohols with ynones for the synthesis of 3-carbonyl quinolines is reported. The reactions proceed to afford 3-carbonyl quinoline derivatives with or without substituent at the C-4 position in good to high yields using Iron(III) chloride hexahydrate as the catalyst in the air. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.106

文献信息

• Copper-catalyzed one-pot domino reactions <i>via</i> C–H bond activation: synthesis of 3-aroylquinolines from 2-aminobenzylalcohols and propiophenones under metal–organic framework catalysis
  作者：Ha V. Dang、Hoang T. B. Le、Loan T. B. Tran、Hiep Q. Ha、Ha V. Le、Nam T. S. Phan

  DOI：10.1039/c8ra05459b

  日期：——

  A Cu2(OBA)2(BPY) metal–organic framework was utilized as a productive heterogeneous catalyst for the synthesis of 3-aroylquinolines via one-pot domino reactions of 2-aminobenzylalcohols with propiophenones. This Cu-MOF was considerably more active towards the one-pot domino reaction than a series of transition metal salts, as well as nano oxide and MOF-based catalysts. The MOF-based catalyst was reusable

  Cu 2 (OBA) 2 (BPY) 金属有机骨架被用作生产多相催化剂，通过 2-氨基苄醇与苯丙酮的一锅多米诺反应合成 3-芳酰基喹啉。与一系列过渡金属盐以及纳米氧化物和 MOF 基催化剂相比，这种 Cu-MOF 对一锅多米诺反应的活性要高得多。基于 MOF 的催化剂可重复使用，催化效率不会显着下降。据我们所知, 2-氨基苯甲醇向 3-芳基喹啉的转化以前没有在文献中报道过, 该协议将与以前合成这些有价值的杂环的策略相辅相成。
• Acid-promoted metal-free synthesis of 3-ketoquinolines from amines, enaminones and DMSO
  作者：Tao-Shan Jiang、Yuhui Zhou、Long Dai、Xiaojun Liu、Xiuli Zhang

  DOI：10.1016/j.tetlet.2019.07.010

  日期：2019.8

  A metal-free p-toluenesulfonic acid (TsOH·H2O) mediated synthesis of 3-ketoquinolines from anilines, enaminones and DMSO has been developed. In this transformation, DMSO was activated by TsOH·H2O and provided the one-carbon unit of the 3-ketoquinolines. A plausible mechanism involving an electrophilic sulfenium ion intermediate was proposed.

  已开发了一种无金属的对甲苯磺酸（TsOH·H 2 O）介导的苯胺，烯胺酮和DMSO合成3-酮喹啉的方法。在该转化中，DMSO被TsOH·H 2 O活化，并提供了3-酮喹啉的一个碳原子单元。提出了一种涉及亲电子ion离子中间体的合理机理。
• Regioselective three-component synthesis of 2,3-disubstituted quinolines <i>via</i> the enaminone modified Povarov reaction
  作者：Yi Li、Xiaoji Cao、Yunyun Liu、Jie-Ping Wan

  DOI：10.1039/c7ob02411h

  日期：——

  The regioselective construction of functionalized quinolines by the three-component reactions of enaminones, aldehydes and anilines is accomplished. Unlike conventional Povarov reactions employing terminal alkynes or alkenes as C3–C4 fragment sources which provide 2,4-disubstituted quinolines, the present method allows fast and regioselective formation of 2,3-disubstituted quinolines as a modified

  通过烯胺酮，醛和苯胺的三组分反应实现了功能化喹啉的区域选择性构建。与常规的Povarov反应不同，后者采用末端炔烃或烯烃作为C3-C4片段来源，提供2，4-二取代的喹啉，本方法允许快速和区域选择性地形成2,3-二取代的喹啉，作为Povarov反应的改进形式。