6-methyl-2-phenyl-1H-1,5,7-triazacyclopenta[c,d]phenalene | 1223157-09-2

• 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: 6-methyl-2-phenyl-1H-1,5,7-triazacyclopenta[c,d]phenalene
• 英文别名: 6-methyl-2-phenyl-1H-1,5,7-triazacyclopenta[cd]phenalene；6-Methyl-13-phenyl-5,7,12-triazatetracyclo[6.5.2.04,15.011,14]pentadeca-1(13),2,4(15),5,7,9,11(14)-heptaene；6-methyl-13-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: 1223157-09-2
• 化学式: C₁₉H₁₃N₃
• 分子量: 283.332
• InChiKey: XUWIVJITUHQPHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-methyl-1H-perimidine 在 ammonium hydroxide 作用下， 反应 3.0h， 生成 6-methyl-2-phenyl-1H-1,5,7-triazacyclopenta[c,d]phenalene
  参考文献：
  名称：

  哌啶与硝基乙烷和酰化剂在多磷酸中的新一锅法反应

  摘要：

  DOI：

  10.1007/s11172-014-0648-x

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.
• 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.
• New one pot synthesis of 1H-1,5,7-triazacyclopenta[c,d]phenalenes
  作者：A. S. Lyakhovnenko、N. A. Aksenov、A. S. Kolesnikova、I. V. Aksenova、A. V. Aksenov

  DOI：10.1007/s11172-013-0117-y

  日期：2013.3
• Novel one-pot synthesis of 1H-1,5,7-triazacyclopenta[c,d]phenalenes
  作者：A. V. Aksenov、A. S. Lyakhovnenko、T. S. Perlova、I. V. Aksenova

  DOI：10.1007/s10593-011-0709-0

  日期：2011.3