(4-cyclohexylquinolin-3-yl)(phenyl)methanone | 1396548-30-3

• 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: (4-cyclohexylquinolin-3-yl)(phenyl)methanone
• 英文别名: 4-cyclohexylquinolin-3-yl(phenyl)methanone；(4-Cyclohexylquinolin-3-yl)-phenylmethanone
• CAS: 1396548-30-3
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: MSAJDRCLFCHKEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  N-(2-(cyclohexanecarbonyl)phenyl)-4-methylbenzenesulfonamide 、 1-苯基-2-丙炔-1-酮 在 三苯基膦 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 6.58h， 以75%的产率得到(4-cyclohexylquinolin-3-yl)(phenyl)methanone
  参考文献：
  名称：

  One-Pot Phosphine-Catalyzed Syntheses of Quinolines

  摘要：

  In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the beta-phosphonium enoate alpha-vinyl anion generated in situ through nucleophilic addition of PPh3 to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.

  DOI：

  10.1021/jo3015825

文献信息

• ZnCl2-promoted Friedländer-type synthesis of 4-substituted 3-aroyl quinolines from o-aminoaryl ketones and enaminones
  作者：Laichun Luo、Zongbao Zhou、Jiayi Zhu、Xue Lu、Hong Wang

  DOI：10.1016/j.tetlet.2016.09.087

  日期：2016.11

  A practical synthesis of 4-substituted 3-aroyl quinolines via Friedländer-type reaction from readily available o-aminoaryl ketones and enaminones was developed. In the presence of ZnCl2, the reaction proceeded smoothly affording the desired products with various functional groups in moderate to good yields.

  通过容易获得的邻氨基芳基酮和烯胺酮的弗里德兰德型反应，开发了一种实用的合成4-取代的3-芳基喹啉的方法。在ZnCl 2的存在下，反应平稳进行，以中等至良好的产率提供具有各种官能团的所需产物。