1-methyl-8-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-methyl-8-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 1-Methyl-8-piperazin-1-yl-3,4-dihydroquinolin-2-one
• 化学式: C₁₄H₁₉N₃O
• 分子量: 245.324
• InChiKey: HKZGCTQRCMYGCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘苄醇 在 重铬酸吡啶 、 四(三苯基膦)钯 、 甲酸 、 norbornene 、 silica gel 、 caesium carbonate 、 三乙胺 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 45.0h， 生成 1-methyl-8-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C–N Bond Formation

  摘要：

  A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and, are present in bioactive, molecules. This work highlights the challenge Of competing intra-vs intermolecular palladium-catalyzed processes.

  DOI：

  10.1021/acs.orglett.7b03577

文献信息

• Palladium-Catalyzed, Norbornene-Mediated, <i>ortho</i>-Amination <i>ipso</i>-Amidation: Sequential C–N Bond Formation
  作者：Andrew Whyte、Maxwell E. Olson、Mark Lautens

  DOI：10.1021/acs.orglett.7b03577

  日期：2018.1.19

  A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and, are present in bioactive, molecules. This work highlights the challenge Of competing intra-vs intermolecular palladium-catalyzed processes.