2-phenylbenzo[gh]perimidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-phenylbenzo[gh]perimidine
• 英文别名: 2-phenyl-1,3-diazapyrene；6-phenyl-5,7-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),5,7,9,11,13-octaene
• 化学式: C₂₀H₁₂N₂
• 分子量: 280.329
• InChiKey: NONMABWTLSINTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C₂₂H₁₉N₃ 在 PPA 作用下， 以0.19 g的产率得到2-phenylbenzo[gh]perimidine
  参考文献：
  名称：

  由苯并[f]喹唑啉合成1,3-二氮杂py烯

  摘要：

  Methods have been developed for the synthesis of 1,3-diazapyrenes based on the reactions of 1-methylbenzo[f]quinazolines with DMF dimethyl acetal or with 1,3,5-triazine in PPA.

  DOI：

  10.1007/s10593-008-0028-2

文献信息

• Novel three-component reaction of perimidines with 1,3,5-triazines and carbonyl compounds in polyphosphoric acid. an efficient method for peri-annelation of a carbocyclic and pyridine ring
  作者：A. V. Aksenov、N. A. Aksenov、A. S. Lyakhovnenko、A. B. Kumshaeva、I. V. Aksenova

  DOI：10.1007/s10593-012-1037-8

  日期：2012.7

  Methods have been developed for the synthesis of 1,3-diazapyrenes, 8(6)-aryl-6(8)-oxo-1,6,7,8-tetra-hydro-1,3-diazapyrenes, and 1,3,7-triazapyrenes based on a three-component reaction of perimidines with 1,3,5-triazines and carbonyl compounds, benzonitrile, or vinyl butyl ether in polyphosphoric acid.

  已经开发出用于合成1,3-二氮杂戊烯，8（6）-芳基-6（8）-氧代-1,6,7,8-四氢-1,3-二氮杂戊烯和1,3的方法，7-三氮杂py烯基于多im啶与1,3,5-三嗪和羰基化合物，苄腈或乙烯基丁基醚在多磷酸中的三组分反应。
• Pyrimidines as Surrogates for 1,3-Dicarbonyl Compounds in<i>peri</i>Annulation of Perimidines en Route to 1,3-Diazapyrenes
  作者：Alexander V. Aksenov、Stanisvlav V. Shcherbakov、Irina V. Lobach、Inna V. Aksenova、Michael Rubin

  DOI：10.1002/ejoc.201601589

  日期：2017.3.27

  A highly efficient protocol for acid-mediated peri-annulation of perimidines with pyrimidines was developed. Pyrimidines, used as surrogates for 1,3-dicarbonyl compounds allow for furnishing benzo[gh]perimidines, including hardly available analogs, non-substituted, or mono-substituted at C-6, C-8. Limitations of reactions employing 5-bromopyrimidines are investigated.

  开发了一种用于酸介导的嘧啶环化环化的高效方案。用作 1,3-二羰基化合物替代物的嘧啶允许提供苯并[gh] 嘧啶，包括几乎无法获得的类似物、未取代的或在 C-6、C-8 处单取代的类似物。研究了使用 5-溴嘧啶的反应的局限性。
• Synthesis of 1,3-diazapyrenes by vinylformylation of perimidines
  作者：I. V. Aksenova、A. S. Lyakhovnenko、A. V. Aksenov、I. V. Borovlev

  DOI：10.1134/s1070363207090277

  日期：2007.9