1-N',2-N'-bis(4-tert-butylphenyl)ethanediimidamide

• 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: 1-N',2-N'-bis(4-tert-butylphenyl)ethanediimidamide
• 化学式: C₂₂H₃₀N₄
• 分子量: 350.507
• InChiKey: FTETUZGYPCGEJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  原甲酸三丙酯 、 1-N',2-N'-bis(4-tert-butylphenyl)ethanediimidamide 反应 10.0h， 以21%的产率得到2,5-Di-n-propoxy-1,4-di-p-tert-butylphenyl-1,2,4,5-tetrahydroimidazo[4,5-d]imidazole
  参考文献：
  名称：

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

  摘要：

  DOI：
• 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 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到1-N',2-N'-bis(4-tert-butylphenyl)ethanediimidamide
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• New Derivatives of Quinoxaline – Syntheses, Complex Formation and their Application as Controlling Ligands for Zinc Catalyzed Epoxide-CO₂–Copolymerization
  作者：O. Hampel、C. Rode、D. Walther、R. Beckert、H. Görls

  DOI：10.1515/znb-2002-0816

  日期：2002.8.1

  A series of amino-(type 3) as well as hydrazino-substituted quinoxalines (type 8) have been synthesized in order to study their ability to complex with iron(III) and zinc(II) ions. Cyclization of 2,3-dichloroquinoxaline (1) with a bis-amidine 9 leads to ring-fused quinoxalines of type 10. One of these compounds (10a) forms a unique macrocyclic hexameric complex 14 with zinc ions in the presence of 2,6-diisopropyl phenolate. In an analogous manner, the monomeric complexes 12 and 13 could be synthesized. All of these new zinc complexes catalyze the copolymerization of cyclohexene oxide and carbon dioxide with a high degree of selectivity in the resulting polymers.

  一系列氨基（3型）和肼基取代的喹喔啉（8型）已经合成，以研究它们与铁（III）和锌（II）离子配合的能力。2,3-二氯喹喔啉（1）与双胺基9环化，形成10型的融合环喹喔啉。其中一种化合物（10a）与2,6-二异丙基酚酸存在下形成了独特的大环六聚物配合物14。类似地，可以合成单体配合物12和13。所有这些新的锌配合物都能高度选择性地催化环己氧化物和二氧化碳的共聚反应，形成高分子聚合物。
• Novel Dihydropyrazines and their Double ortho-Annulation to Hexaazapentacenes
  作者：Rainer Strathausen、Rainer Beckert、Jan Fleischhauer、Dirk Müller、Helmar Görls

  DOI：10.5560/znb.2014-4002

  日期：2014.5.1

  The cycloacylation of oxalic amidines 7 with bis-imidoylchlorides 6 furnished the dihydropyrazine derivatives 8. Due to their vicinal amino-imino substructures, they provide good preconditions for a double intramolecular ring closure reaction. An alternative synthesis for hexaaza-pentacenes 1 was developed using potassium carbonate as the base and lead tetraacetate as the oxidizing agent.

  草氨酸脒 7 与双咪唑酰氯 6 环酰化反应生成了二氢吡嗪衍生物 8。由于它们具有邻氨基亚氨基亚结构，因此为双分子内闭环反应提供了良好的先决条件。使用碳酸钾作为碱，四乙酸铅作为氧化剂，开发出了六氮杂并五苯 1 的另一种合成方法。
• The Introduction of OH and COOH Groups into 4<i>H</i>-Imidazoles: Water-Soluble Functional Dyes and Quinomethides
  作者：Rainer Beckert、Martin Matschke、Lenka Kubicova、Christoph Biskup

  DOI：10.1055/s-2008-1067249

  日期：2008.9

  Water-soluble 4H-imidazoles, which represent redox- as well as pH-switchable functional dyes, are synthesized via a novel procedure. In a smooth reaction, phthalic anhydride reacts with oxalic acid amidine 5 yielding 4H-imidazole 1a. Analogously, but in lower yields, naphthalene-1,8-dicarboxylic anhydride and 2-sulfobenzoic anhydride can be transformed into 4H-imidazoles 1b,c. 4-Hydroxybenzoic acids do not form the expected 4H-imidazoles, which possess hydroxyaryl substructures. However, in the course of the cyclization-long-range prototropism sequence, the new quinomethides 7a-c were obtained. This sequence could be adapted successfully for the synthesis of corresponding thioxo derivatives 7d. The water-soluble 4H-imidazoles 1a-c as well as quino­methides of type 7 proved to be multifunctional and switchable dyes. They show acidochromism and in addition, can be transformed into fluorescent leuco forms, which reoxidize when exposed to air.

  水溶性 4H-咪唑，代表氧化还原和 pH 可切换的功能染料，是通过一种新的方法合成的。在顺利的反应中，邻苯二甲酸酐与草酸脒 5 反应生成 4H-咪唑 1a。类似地，1,8-萘二甲酸酐和2-磺基苯甲酸酐可以转化为4H-咪唑1b,c，但产率较低。 4-羟基苯甲酸不会形成预期的具有羟基芳基子结构的4H-咪唑。然而，在环化-长程向质子序列过程中，获得了新的喹诺酮化合物7a-c。该序列可以成功地用于合成相应的硫代衍生物7d。水溶性 4H-咪唑 1a-c 以及 7 型喹甲基化物被证明是多功能且可转换的染料。它们表现出酸变色性，此外，可以转化为荧光无色形式，当暴露在空气中时会重新氧化。
• 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)
• Ketene-N,N-acetals as Key Intermediates in the Formation of Tetraazapentafulvadienes
  作者：Dirk Müller、Rainer Beckert、Jennie Weston、Wolfgang Günther、Helmar Görls、Manfred Friedrich

  DOI：10.1002/1099-0690(200112)2001:23<4551::aid-ejoc4551>3.0.co;2-9

  日期：2001.12

  The easily accessible bis-amidines 2 react with adamantane-1-carbonyl chloride 3 to yield the 4H-imidazole 4. If the carbonic acid chloride contains an alpha -hydrogen, the reaction takes a completely different path. In this case, tetraazapen-tafulvadienes 11 are formed via a cascade reaction that contains two single electron transfer (SET) steps. Cyclic ketene-N,N-acetals 7 are postulated to be the initial intermediates, which then readily form radical cations, the presence of which could be confirmed by ESR measurements even though intramolecular trapping proved impossible due to their extreme reactivity. DFT calculations at the B3LYP/6311+G(d,p) level support these experimental findings. The crucial ketene-N,N-acetals 7 can be stabilized through steric interactions and/or the introduction of conjugated substructures, thus leading to the formation of fulvenoid structures such as 14a and 14b.