6-phenyl-1H-1,5,7-triazacyclopenta[c,d]phenalene | 1223157-03-6

• 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: 6-phenyl-1H-1,5,7-triazacyclopenta[c,d]phenalene
• 英文别名: 6-phenyl-1H-1,5,7-triazacyclopenta[cd]phenalene；2-phenyl-6H-pyrrolo[2,3,4-gh]perimidine；6-phenyl-5,7,12-triazatetracyclo[6.5.2.04,15.011,14]pentadeca-1(13),2,4(15),5,7,9,11(14)-heptaene
• CAS: 1223157-03-6
• 化学式: C₁₈H₁₁N₃
• 分子量: 269.305
• InChiKey: ASHSPKAKQSRSAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-phenylperimidine 在 sodium azide 作用下， 反应 8.0h， 生成 6-phenyl-1H-1,5,7-triazacyclopenta[c,d]phenalene
  参考文献：
  名称：

  在多磷酸中高效一锅合成6H-吡咯并[2,3,4-gh] perimidines的合理设计

  摘要：

  开发了几种高效的一锅法合成方案，使多磷酸活化的硝基烷烃在与氨基萘的反应中充当亲电试剂。特色方法允许单步组装...

  DOI：

  10.1039/c6ra17269e

文献信息

• 6(7)-Acylperimidines nitration and methods of peri-annelation on this base
  作者：A. V. Aksenov、N. A. Aksenov、A. S. Lyakhovnenko、A. N. Smirnov、I. I. Levina、I. V. Aksenova

  DOI：10.1007/s10593-013-1335-9

  日期：2013.10

  A method has been developed for the nitration of 6(7)-acylperimidines using sodium nitrite in formic acid. The reaction gives a mixture of 4(9)-, 9(4)-, and 7(6)-nitro-6(7)-acylperimidines from which the latter can be separated by extraction with chloroform. Reduction of the 6(7)-acyl-7(6)-nitro- perimidines yields 1H-1,5,7-triazacyclopenta[cd]phenalenes. Subsequent Schmidt reaction and reduction give 1,3,6,8-tetraazapyrenes.
• New one-pot reaction of perimidines with nitroethane and acylating agents in polyphosphoric acid
  作者：A. V. Aksenov、N. A. Aksenov、A. N. Smirnov、V. I. Goncharov、S. N. Ovcharov、I. V. Aksenova

  DOI：10.1007/s11172-014-0648-x

  日期：2014.7
• A new method for pyrrole peri-annulation: synthesis of 1H-1,5,7-triazacyclopenta[c,d]phenalenes from 1H-perimidines
  作者：Alexander V. Aksenov、Alexander S. Lyakhovnenko、Anna V. Andrienko、Irina I. Levina

  DOI：10.1016/j.tetlet.2010.02.129

  日期：2010.5

  New methods for the synthesis of 1H-1,5,7-triazacyclopenta[c,d]phenalenes have been developed based on a sequence involving Schmidt reaction of keto-perimidines and acylation of the intermediate amides with 1,3,5-triazines or carboxylic acids. The same synthetic sequence starting from the corresponding alkylperimidine includes acylation with acetic acid as the first step. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of 1H-1,5,7-triazacyclopenta[c,d]phenalenes by the electrophilic amination of perimidines using sodium azide in PPA
  作者：A. V. Aksenov、A. S. Lyakhovnenko、A. V. Andrienko

  DOI：10.1007/s10593-011-0662-y

  日期：2011.1

  A method was developed for the synthesis of 1H-1,5,7-triazacyclopenta[c,d]phenalenes by the electrophilic amination of perimidines using the new sodium azide/PPA reagent system and a subsequent one-pot reaction with 1,3,5-triazines. A multicomponent variant of this reaction is possible in the case of 2,4,6-trimethyl- and 2,4,6-triphenyl-1,3,5-triazines.