(E)-2-methyl-N-(5-cinnamylquinolin-8-yl)benzamide | 1616877-73-6

• 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: (E)-2-methyl-N-(5-cinnamylquinolin-8-yl)benzamide
• 英文别名: 2-methyl-N-[5-[(E)-3-phenylprop-2-enyl]quinolin-8-yl]benzamide
• CAS: 1616877-73-6
• 化学式: C₂₆H₂₂N₂O
• 分子量: 378.473
• InChiKey: IDQYPFHLBVIURZ-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-methylbenzoyl)-8-aminoquinoline 、 tert-butyl (E)-cinnamyl carbonate 在 iron(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 30.0h， 以65%的产率得到(E)-2-methyl-N-(5-cinnamylquinolin-8-yl)benzamide
  参考文献：
  名称：

  Iron-Catalyzed, Chelation-Induced Remote C–H Allylation of Quinolines via 8-Amido Assistance

  摘要：

  An iron-catalyzed, 8-amido-enabled regiodivergent C-H allylation of quinolines is described. This reaction represents a rare example of chelation-induced geometrically inaccessible C-H functionalization, allowing for the highly regio- and stereoselective preparation of either the C5- or the C4-allylated quinoline scaffolds regiocontrolled by the catalytic systems.

  DOI：

  10.1021/ol501534z

文献信息

• Iron-Catalyzed, Chelation-Induced Remote C–H Allylation of Quinolines via 8-Amido Assistance
  作者：Xuefeng Cong、Xiaoming Zeng

  DOI：10.1021/ol501534z

  日期：2014.7.18

  An iron-catalyzed, 8-amido-enabled regiodivergent C-H allylation of quinolines is described. This reaction represents a rare example of chelation-induced geometrically inaccessible C-H functionalization, allowing for the highly regio- and stereoselective preparation of either the C5- or the C4-allylated quinoline scaffolds regiocontrolled by the catalytic systems.