3-chloro-4-(4-methylphenyl)benzo[g]quinoline-5,10-dione | 1315369-85-7

• 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: 3-chloro-4-(4-methylphenyl)benzo[g]quinoline-5,10-dione
• 英文别名: 3-Chloro-4-(4-methylphenyl)benzo[g]quinoline-5,10-dione
• CAS: 1315369-85-7
• 化学式: C₂₀H₁₂ClNO₂
• 分子量: 333.774
• InChiKey: LILQLMQSRJIJHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[3-(4-methylphenyl)-2-propynylamino]-1,4-naphthoquinone 在 copper dichloride 作用下， 以 硝基甲烷 为溶剂， 反应 4.0h， 以86%的产率得到3-chloro-4-(4-methylphenyl)benzo[g]quinoline-5,10-dione
  参考文献：
  名称：

  CuCl₂-Promoted 6-endo-dig Chlorocyclization and Oxidative Aromatization Cascade: Efficient Construction of 1-Azaanthraquinones from N-Propargylaminoquinones

  摘要：

  An efficient synthetic methodology was developed to assemble 1-azaanthraquinones from N-propargylaminoquinones by copper(II)-promoted sequential 6-endo-dig chlorocyclization and oxidative aromatization. The approach can be extended to preprare chlorinated alkaloids such as cleistophine and sampangine. A possible mechanism involving carbon-carbon bond formation triggered by regioselective electrophilic activation and carbon-chlorine bond formation via reductive elimination was proposed.

  DOI：

  10.1021/ol201542h

文献信息

• CuCl₂-Promoted 6-<i>endo-dig</i> Chlorocyclization and Oxidative Aromatization Cascade: Efficient Construction of 1-Azaanthraquinones from <i>N</i>-Propargylaminoquinones
  作者：Na Fei、Hao Yin、Shaozhong Wang、Huaqin Wang、Zhu-Jun Yao

  DOI：10.1021/ol201542h

  日期：2011.8.19

  An efficient synthetic methodology was developed to assemble 1-azaanthraquinones from N-propargylaminoquinones by copper(II)-promoted sequential 6-endo-dig chlorocyclization and oxidative aromatization. The approach can be extended to preprare chlorinated alkaloids such as cleistophine and sampangine. A possible mechanism involving carbon-carbon bond formation triggered by regioselective electrophilic activation and carbon-chlorine bond formation via reductive elimination was proposed.