2,3,6,7-Tetrakis(4-tert-butylphenylamino)-1,4,5,8-tetraazafulvalene | 189115-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,6,7-Tetrakis(4-tert-butylphenylamino)-1,4,5,8-tetraazafulvalene
• 英文别名: 2-[4,5-bis[(4-tert-butylphenyl)imino]imidazolidin-2-ylidene]-4-N,5-N-bis(4-tert-butylphenyl)imidazolidine-4,5-diimine
• CAS: 189115-05-7
• 化学式: C₄₆H₅₆N₈
• 分子量: 721.004
• InChiKey: RBCKWWKALSZKGC-UHFFFAOYSA-N

物化性质

• 沸点：
  716.5±70.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  54
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,6,7-Tetrakis(4-tert-butylphenylamino)-1,4,5,8-tetraazafulvalene 在 sodium dithionite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.25h， 以97%的产率得到N⁴,N⁵,N^4',N^5'-Tetrakis-(4-tert-butyl-phenyl)-1H,1'H-[2,2']biimidazolyl-4,5,4',5'-tetraamine
  参考文献：
  名称：

  The redox behaviour of cyclic tetraaminoethenes derived from 2,2′-biimidazole

  摘要：

  Syntheses and redox chemistry of the nearly unknown 4,4',5,5'-tetraamino derivatives of 2,2'-biimidazole are studied. These cyclic versions of electron-rich ethenes are only stable under strictly anaerobic conditions. In the presence of oxygen, a fast oxidation reaction occurs to form stable, deeply Coloured tetraazafulvalenes. Leuco-forms, however, can be stabilized towards air by acylation reactions. This accounts for the hexa-Boc derivative 6. Based on these findings, we present the first synthesis of tetraazafulvalenes, which possess four peripheric secondary amine functions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.076
• 作为产物：
  描述：

  二氯化乙二亚胺酰基,二[4-(1,1-二甲基乙基)苯基]- 在 氨 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 80.0 ℃ 、500.0 kPa 条件下， 反应 2.0h， 生成 2,3,6,7-Tetrakis(4-tert-butylphenylamino)-1,4,5,8-tetraazafulvalene
  参考文献：
  名称：

  Mueller; Beckert; Goerls, Synthesis, 2001, # 4, p. 601 - 606

  摘要：

  DOI：

文献信息

• Highly Fluorescent Heterocycles Based on Pyrazino Fused 1,4,5,8-Tetra-azafulvalenes
  作者：Rainer Beckert、Christian Käpplinger、Jan Koci、Gabriela Braunerova、Karel Waisser、Helmar Görls

  DOI：10.3987/com-03-9842

  日期：——

  Some new pyrazino-fused 1,4,5,8-tetraazafulvalenes of type (3-5) were synthesized and their structures were confirmed by IR, UV-VIS, 1 H NMR spectra and elemental analysis. The X-Ray crystal structure analysis of a singlecrystal of derivative (3c) revealed a nearly ideal planarized heterofulvalene subunit. The new prepared tricyclic tetraazafulvalenes of type (3) show strong red fluorescence at 605

  合成了一些新型吡嗪稠合1,4,5,8-四氮杂富瓦烯(3-5)，并通过IR、UV-VIS、1 H NMR光谱和元素分析证实了它们的结构。衍生物 (3c) 的单晶的 X 射线晶体结构分析揭示了一个近乎理想的平面化异富瓦烯亚基。新制备的 (3) 型三环四氮杂富瓦烯在 605 nm 处显示出强烈的红色荧光。
• Polyazaacenes – On the Way to Stable, Fluorescent and Redox-Active Derivatives
  作者：Frances Stöckner、Rainer Beckert、Dieter Gleich、Eckhard Birckner、Wolfgang Günther、Helmar Görls、Gavin Vaughan

  DOI：10.1002/ejoc.200600803

  日期：2007.3

  polyazaacenes is described starting from two different nucleophilic building blocks. Disubstituted oxalic amidines 1 can be cyclized under mild conditions with 2,3-dichloro-5,6-dicyanopyrazine (3) to yield 5,6-dihydropyrazino[2,3-b]pyrazines 4a–c. By employing higher temperatures and 2 equiv. of 3, octaazanaphthacene 6 can be isolated. Similarly, pyrazino[2,3-b]pyrazines 2 and bielectrophile 3 yielded novel

  描述了一种从两种不同的亲核结构单元开始制备聚氮杂并苯的新合成方法。双取代的草酸脒 1 可以在温和条件下与 2,3-二氯-5,6-二氰基吡嗪 (3) 环化，得到 5,6-二氢吡嗪并 [2,3-b] 吡嗪 4a-c。通过采用更高的温度和 2 当量。3、八氮杂萘6可以被分离出来。类似地，除了半环化衍生物 9 之外，吡嗪并 [2,3-b] 吡嗪 2 和双亲电子试剂 3 还产生了新的十二氮杂六苯 8。当四氮杂富瓦烯 10d 在二甲苯中在氧气存在的情况下加热时，八氮杂六苯 13 分离为主要产品。代替吡嗪并[2,3-b]吡嗪2，这种高度荧光的聚氮杂并苯是通过级联反应形成的，该反应涉及一个dytropic重排，分子内 Diels-Alder 反应和多步氧化还原反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• New tetraazafulvadienes via cascade reactions and their cyclizations to diazaborolidines
  作者：Christian Käpplinger、Tillmann Gebauer、Rainer Beckert、Dieter Weiß、Wolfgang Günther、Helmar Görls、Manfred Friedrich

  DOI：10.1016/j.tet.2004.03.012

  日期：2004.4

  3,4,5,6-Tetrahydro-2-aminopyridine reacts with bis-imidoylchlorides derived from oxalic acid to yield new dimeric tetraazafulvadienes. Ketene aminals could be isolated and characterized as key intermediates in a cascade reaction (cyclization-prototropism-oxidation-dimerization-deprotonation). The stable tetraazafulvadienes have been transformed with boron compounds into highly fluorescent tricyclic diazaborolidines. (C) 2004 Published by Elsevier Ltd.
• Mueller; Beckert; Goerls, Synthesis, 2001, # 4, p. 601 - 606
  作者：Mueller、Beckert、Goerls

  DOI：——

  日期：——
• The redox behaviour of cyclic tetraaminoethenes derived from 2,2′-biimidazole
  作者：M. Matschke、C. Käpplinger、D. Weiß、R. Beckert

  DOI：10.1016/j.tetlet.2005.09.076

  日期：2005.11

  Syntheses and redox chemistry of the nearly unknown 4,4',5,5'-tetraamino derivatives of 2,2'-biimidazole are studied. These cyclic versions of electron-rich ethenes are only stable under strictly anaerobic conditions. In the presence of oxygen, a fast oxidation reaction occurs to form stable, deeply Coloured tetraazafulvalenes. Leuco-forms, however, can be stabilized towards air by acylation reactions. This accounts for the hexa-Boc derivative 6. Based on these findings, we present the first synthesis of tetraazafulvalenes, which possess four peripheric secondary amine functions. (c) 2005 Elsevier Ltd. All rights reserved.