5-phenyl-5H-benzo[b]carbazole-6,11-dione | 56568-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-phenyl-5H-benzo[b]carbazole-6,11-dione
• 英文别名: 5-Phenylbenzo[b]carbazole-6,11-dione
• CAS: 56568-51-5
• 化学式: C₂₂H₁₃NO₂
• 分子量: 323.351
• InChiKey: QDXNNIMTIZOINB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-phenyl-3-(phenylamino)naphthalene-1,4-dione 以22%的产率得到
  参考文献：
  名称：

  FORRESTER A. R.; INGRAM A. S.; JOHN I. L.; THOMSON R. H., J. CHEM. SOC. PERKIN TRANS. PART I, , 1975, NO 12, 1115-1120

  摘要：

  DOI：

文献信息

• Synthesis of Carbazolequinones by Formal [3 + 2] Cycloaddition of Arynes and 2-Aminoquinones
  作者：Jian Guo、I. N. Chaithanya Kiran、R. Santhosh Reddy、Jiangsheng Gao、Meiqiong Tang、Yuyin Liu、Yun He

  DOI：10.1021/acs.orglett.6b01090

  日期：2016.5.20

  A formal cycloaddition reaction for the synthesis of biologically and pharmaceutically important carbazolequinones via the annulation of aminoquinones with arynes has been developed. This practical and metal-free cascade reaction proceeds through successive C–C/C–N bond formations. Moreover, this novel method has been utilized for the concise synthesis of bioactive murrayaquinone A and koeniginequinone

  已经开发了一种正式的环加成反应，用于通过氨基醌与芳烃的环合反应合成生物学上和药学上重要的咔唑醌。这种实用且无金属的级联反应是通过连续的C–C / C–N键形成而进行的。此外，该新方法已被用于简明合成生物活性的墨瑞亚醌A和甲烯乙醌B及其类似物。
• Novel Synthesis of 5-Substituted 5H-Benzo[b]carbazole-6,11-diones via Double Buchwald–Hartwig Reaction
  作者：Patrice Vanelle、Khrystyna Bolibrukh、Omar Khoumeri、Svyatoslav Polovkovych、Volodymyr Novikov、Thierry Terme

  DOI：10.1055/s-0034-1379235

  日期：——

  2-Bromo-3-(2-bromophenyl)naphthalene-1,4-dione was synthesized as a key precursor to obtain a number of functionalized benzo[b]carbazole-6,11-diones by double Buchwald–Hartwig coupling reaction.

  合成了 2-Bromo-3-(2-bromophenyl)naphthalene-1,4-dione 作为关键前体，通过双 Buchwald-Hartwig 偶联反应获得了许多功能化的苯并[b]咔唑-6,11-二酮。
• One-Pot Palladium-Catalyzed Synthesis of Benzo[b]carbazolediones
  作者：Peter Langer、Hoang Do、Hung Tran、Lars Ohlendorf、Thang Ngo、Tuan Dang、Peter Ehlers、Alexander Villinger

  DOI：10.1055/s-0035-1560212

  日期：——

  A palladium-catalyzed one-pot reaction for the synthesis of benzo[b]carbazolediones is described which proceeds by amination of 2,3-dibromonaphthoquinone, Suzuki cross-coupling with (2-bromophenyl)boronic acid, and subsequent intramolecular C-N Buchwald-Hartwig cyclization with amines.