N,N'-bis(2-propenyl)-1,4,5,8-naphthalenetetracarboxylic acid diimide | 134174-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N'-bis(2-propenyl)-1,4,5,8-naphthalenetetracarboxylic acid diimide
• 英文别名: 2,7-Di-2-propen-1-ylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone；6,13-bis(prop-2-enyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 134174-27-9
• 化学式: C₂₀H₁₄N₂O₄
• 分子量: 346.342
• InChiKey: AEGCQYRQOZWBJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-propenyl)-1,4,5,8-naphthalenetetracarboxylic acid diimide 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以68%的产率得到1,3,6,8-tetrahydro-2,7-bis(2-propenyl)-2,7-diazapyrene
  参考文献：
  名称：

  A Convenient Synthesis and Spectroscopic Characterization of N,N‘-Bis(2-propenyl)-2,7-diazapyrenium Quaternary Salts

  摘要：

  N,N'-Bis(2-propenyl)-2,7-diazapyrenium salts are synthesized in good yield from the reaction of 1,4,5,8-naphthalenetetracarboxylic dianhydride with allylamine, followed by LiAlH4 reduction and subsequent oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The nature of the counteranion depends on the solvent system used for recrystallization of the crude product from the final DDQ-oxidation step. X-ray analysis shows that if recrystallization is carried out in boiling CH3OH/H2O (1:1, v/v), the counteranion in the resulting deep-red crystals is always the alkoxy anion of 2-cyano-5,6-dichloro-3-hydroxy-1,4-benzoquinone whether the final DDQ oxidation ends with addition of HClO4 or HCl; on the other hand, if recrystallization is carried out with anhydrous acetonitrile, the product is N,N'-bis(2-propenyl)-2,7-diazapyrenium diperchlorate or dichloride depending on whether the DDQ oxidation is followed by addition of coned HClO4 or coned HCl, respectively. Importantly, if the DDQ oxidation is quenched with HBr, Br- is oxidized to Br-2 by unreacted DDQ, and the resulting product is N,N'-bis(a,3-dibromopropyl)-2,7-diazapyrenium dibromide. Comparative absorption and time-resolved emission studies provide evidence for possible dimerization of N,N'-bis(2-propenyl)-2,7-diazapyrenium diperchlorate in CH3CN.

  DOI：

  10.1021/jo0004557
• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 、 丙烯胺 以 水 为溶剂， 反应 6.0h， 以95%的产率得到N,N'-bis(2-propenyl)-1,4,5,8-naphthalenetetracarboxylic acid diimide
  参考文献：
  名称：

  A Convenient Synthesis and Spectroscopic Characterization of N,N‘-Bis(2-propenyl)-2,7-diazapyrenium Quaternary Salts

  摘要：

  N,N'-Bis(2-propenyl)-2,7-diazapyrenium salts are synthesized in good yield from the reaction of 1,4,5,8-naphthalenetetracarboxylic dianhydride with allylamine, followed by LiAlH4 reduction and subsequent oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The nature of the counteranion depends on the solvent system used for recrystallization of the crude product from the final DDQ-oxidation step. X-ray analysis shows that if recrystallization is carried out in boiling CH3OH/H2O (1:1, v/v), the counteranion in the resulting deep-red crystals is always the alkoxy anion of 2-cyano-5,6-dichloro-3-hydroxy-1,4-benzoquinone whether the final DDQ oxidation ends with addition of HClO4 or HCl; on the other hand, if recrystallization is carried out with anhydrous acetonitrile, the product is N,N'-bis(2-propenyl)-2,7-diazapyrenium diperchlorate or dichloride depending on whether the DDQ oxidation is followed by addition of coned HClO4 or coned HCl, respectively. Importantly, if the DDQ oxidation is quenched with HBr, Br- is oxidized to Br-2 by unreacted DDQ, and the resulting product is N,N'-bis(a,3-dibromopropyl)-2,7-diazapyrenium dibromide. Comparative absorption and time-resolved emission studies provide evidence for possible dimerization of N,N'-bis(2-propenyl)-2,7-diazapyrenium diperchlorate in CH3CN.

  DOI：

  10.1021/jo0004557

文献信息

• A Convenient Synthesis and Spectroscopic Characterization of <i>N,N</i><i>‘</i>-Bis(2-propenyl)-2,7-diazapyrenium Quaternary Salts
  作者：Chariklia Sotiriou-Leventis、Zhan Mao、Abdel-Monem M. Rawashdeh

  DOI：10.1021/jo0004557

  日期：2000.9.1

  N,N'-Bis(2-propenyl)-2,7-diazapyrenium salts are synthesized in good yield from the reaction of 1,4,5,8-naphthalenetetracarboxylic dianhydride with allylamine, followed by LiAlH4 reduction and subsequent oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The nature of the counteranion depends on the solvent system used for recrystallization of the crude product from the final DDQ-oxidation step. X-ray analysis shows that if recrystallization is carried out in boiling CH3OH/H2O (1:1, v/v), the counteranion in the resulting deep-red crystals is always the alkoxy anion of 2-cyano-5,6-dichloro-3-hydroxy-1,4-benzoquinone whether the final DDQ oxidation ends with addition of HClO4 or HCl; on the other hand, if recrystallization is carried out with anhydrous acetonitrile, the product is N,N'-bis(2-propenyl)-2,7-diazapyrenium diperchlorate or dichloride depending on whether the DDQ oxidation is followed by addition of coned HClO4 or coned HCl, respectively. Importantly, if the DDQ oxidation is quenched with HBr, Br- is oxidized to Br-2 by unreacted DDQ, and the resulting product is N,N'-bis(a,3-dibromopropyl)-2,7-diazapyrenium dibromide. Comparative absorption and time-resolved emission studies provide evidence for possible dimerization of N,N'-bis(2-propenyl)-2,7-diazapyrenium diperchlorate in CH3CN.