3,3-dimethyl-5-(p-tolyl)-3,4-dihydro-1H-benzo[b]carbazole-1,6,11(2H,5H)-trione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,3-dimethyl-5-(p-tolyl)-3,4-dihydro-1H-benzo[b]carbazole-1,6,11(2H,5H)-trione
• 英文别名: 3,3-Dimethyl-5-(4-methylphenyl)-2,4-dihydrobenzo[b]carbazole-1,6,11-trione；3,3-dimethyl-5-(4-methylphenyl)-2,4-dihydrobenzo[b]carbazole-1,6,11-trione
• 化学式: C₂₅H₂₁NO₃
• 分子量: 383.447
• InChiKey: QRQQJTMEZKDWTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,5-二甲基-3-(4-甲基苯胺基)环己-2-烯-1-酮 、 1,4-萘醌 在 氧气 、 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以91%的产率得到3,3-dimethyl-5-(p-tolyl)-3,4-dihydro-1H-benzo[b]carbazole-1,6,11(2H,5H)-trione
  参考文献：
  名称：

  Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under Base-Free Condition

  摘要：

  An efficient synthesis of benzo[f]indole-4,9-diones has been achieved by copper(II)-catalyzed naphthoquinone sequential C,N-difunctionalization reactions with beta-enaminones. New C-C and C-N bonds are easily formed in the reaction course. Copper(II) salt plays a dual role as Lewis acid and oxidative catalyst, and O-2 acts as the terminal oxidant. The advantage of this reaction is the high atom economy with broad substrate scope and excellent yields. The reaction can be scaled up to using at least grams of substrates.

  DOI：

  10.1021/jo401842d

文献信息

• Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[<i>f</i>]indole-4,9-diones under Base-Free Condition
  作者：Jin-Wei Sun、Xiang-Shan Wang、Yun Liu

  DOI：10.1021/jo401842d

  日期：2013.10.18

  An efficient synthesis of benzo[f]indole-4,9-diones has been achieved by copper(II)-catalyzed naphthoquinone sequential C,N-difunctionalization reactions with beta-enaminones. New C-C and C-N bonds are easily formed in the reaction course. Copper(II) salt plays a dual role as Lewis acid and oxidative catalyst, and O-2 acts as the terminal oxidant. The advantage of this reaction is the high atom economy with broad substrate scope and excellent yields. The reaction can be scaled up to using at least grams of substrates.