n-butyl (E)-3-(3-methylquinol-2-yl)acrylate | 1190232-37-1

• 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: n-butyl (E)-3-(3-methylquinol-2-yl)acrylate
• 英文别名: butyl (E)-3-(3-methylquinolin-2-yl)prop-2-enoate
• CAS: 1190232-37-1
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: XQDZBAMZKGRUHB-MDZDMXLPSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  408.2±30.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基喹啉N-氧化物 、 丙烯酸丁酯 在 palladium diacetate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 20.0h， 以90%的产率得到n-butyl (E)-3-(3-methylquinol-2-yl)acrylate
  参考文献：
  名称：

  Palladium-Catalyzed Alkenylation of Quinoline-N-oxides via C−H Activation under External-Oxidant-Free Conditions

  摘要：

  The direct cross-coupling of quinoline-N-oxides with olefin derivatives has been realized using palladium acetate as the catalyst in the absence of external ligand and oxidant to give the corresponding 2-alkenylated quinolines and 1-alkenylated isoquinolines chemo- and regioselectively in 27-95% yield. The catalytic process is proposed to proceed via direct C-H bond activation of the quinoline-N-oxide with Pd(OAc)(2) followed by Heck coupling with the olefin. The resultant N-oxide of the alkenylated quinoline can oxidize the reduced Pd(0) to regenerate the Pd(11) active species and simultaneously release the 2-alkenylated quinoline without using any external oxidants and reductants.

  DOI：

  10.1021/ja902762a

文献信息

• Palladium-Catalyzed Alkenylation of Quinoline-<i>N</i>-oxides via C−H Activation under External-Oxidant-Free Conditions
  作者：Junliang Wu、Xiuling Cui、Lianmei Chen、Guojie Jiang、Yangjie Wu

  DOI：10.1021/ja902762a

  日期：2009.10.7

  The direct cross-coupling of quinoline-N-oxides with olefin derivatives has been realized using palladium acetate as the catalyst in the absence of external ligand and oxidant to give the corresponding 2-alkenylated quinolines and 1-alkenylated isoquinolines chemo- and regioselectively in 27-95% yield. The catalytic process is proposed to proceed via direct C-H bond activation of the quinoline-N-oxide with Pd(OAc)(2) followed by Heck coupling with the olefin. The resultant N-oxide of the alkenylated quinoline can oxidize the reduced Pd(0) to regenerate the Pd(11) active species and simultaneously release the 2-alkenylated quinoline without using any external oxidants and reductants.