ethyl (E)-3-(1-isoquinolyl)acrylate | 1190232-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: ethyl (E)-3-(1-isoquinolyl)acrylate
• 英文别名: ethyl (E)-3-isoquinolin-1-ylprop-2-enoate
• CAS: 1190232-45-1
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: VOGHBMNWDOUQRQ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  异喹啉-N-氧化物 、 丙烯酸乙酯 在 palladium diacetate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 20.0h， 以67%的产率得到ethyl (E)-3-(1-isoquinolyl)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.