11H-benzocarbazole-5,6-dione

• 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: 11H-benzocarbazole-5,6-dione
• 英文别名: 11H-benzo[a]carbazole-5,6-dione；11H-Benzo[a]carbazol-5,6-dion；11H-benzo[a]carbazole-5,6-dione
• 化学式: C₁₆H₉NO₂
• 分子量: 247.253
• InChiKey: RXXLALXYEOBLHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-hydroxy-3-(2-nitrophenyl)naphthalene-1,4-dione 在 platinum(IV) oxide air 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 24.5h， 生成 11H-benzocarbazole-5,6-dione
  参考文献：
  名称：

  A Simple Synthesis of Benzocarbazolequinones via o-Nitroarylation of 2-Hydroxy-1,4-naphthoquinones

  摘要：

  The reaction of 2-hydroxy-1,4-naphthoquinones (la-c) with o-fluoronitrobenzenes (2a,b) in the presence of K2CO3 in DMSO at 100 degrees C gave 2-hydroxy-3-(2-nitroaryl)-1,4-naphthoquinones (3a-e) in moderate to fair yields, which in turn were transformed into the corresponding 11H-benzo[a] carbazole-5,6-dione (6a-e) and SH-benzo[b]carbazole-6, 11-dione (7a-e) derivatives in good yields by catalytic hydrogenation over PtO2 in AcOEt at room temperature and 1 atm, followed by exposure to air and then heating at reflux temperature.

  DOI：

  10.3987/com-98-8364

文献信息

• New vat dyestuffs
  申请人：GEN ANILINE & FILM CORP

  公开号：US02319719A1

  公开（公告）日：1943-05-18
• DE695350
  申请人：——

  公开号：——

  公开（公告）日：——
• US2242449
  申请人：——

  公开号：——

  公开（公告）日：——
• A Simple Synthesis of Benzocarbazolequinones via o-Nitroarylation of 2-Hydroxy-1,4-naphthoquinones
  作者：Kazuhiro Kobayashi、Tetsuya Taki、Masataka Kawakita、Masaharu Uchida、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.3987/com-98-8364

  日期：——

  The reaction of 2-hydroxy-1,4-naphthoquinones (la-c) with o-fluoronitrobenzenes (2a,b) in the presence of K2CO3 in DMSO at 100 degrees C gave 2-hydroxy-3-(2-nitroaryl)-1,4-naphthoquinones (3a-e) in moderate to fair yields, which in turn were transformed into the corresponding 11H-benzo[a] carbazole-5,6-dione (6a-e) and SH-benzo[b]carbazole-6, 11-dione (7a-e) derivatives in good yields by catalytic hydrogenation over PtO2 in AcOEt at room temperature and 1 atm, followed by exposure to air and then heating at reflux temperature.