(E)-2-(3-ethoxy-3-oxoprop-1-enyl)quinoline N-oxide | 1190232-50-8

• 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-(3-ethoxy-3-oxoprop-1-enyl)quinoline N-oxide
• CAS: 1190232-50-8
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: QHEKOXDTRQRJQH-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  53.24
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-甲基喹啉N-氧化物 、 丙烯酸丁酯 、 (E)-2-(3-ethoxy-3-oxoprop-1-enyl)quinoline N-oxide 在 palladium diacetate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 20.0h， 生成 ethyl (E)-3-(quinolin-2-yl)acrylate 、 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
• 作为产物：
  描述：

  ethyl (E)-3-(quinolin-2-yl)acrylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以95%的产率得到(E)-2-(3-ethoxy-3-oxoprop-1-enyl)quinoline N-oxide
  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