2-anilino-3-chloro-5,6-dicyanopyrazine

• 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-anilino-3-chloro-5,6-dicyanopyrazine
• 英文别名: 5-Anilino-6-chloropyrazine-2,3-dicarbonitrile
• 化学式: C₁₂H₆ClN₅
• 分子量: 255.666
• InChiKey: QPJGXXOJHGAEMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-anilino-3-chloro-5,6-dicyanopyrazine 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以38%的产率得到2,3,7,8-tetracyano-5,10-diphenyl-5,10-dihydrodipyrazino[2,3-b:2',3'-e]pyrazine
  参考文献：
  名称：

  2,3,7,8-四氰基-5,10-二氢二吡嗪并[2,3- b：2'，3'- e ]吡嗪的合成及光谱性质

  摘要：

  对2-氨基-3-氯-5,6-二氰基吡嗪进行碱催化的分子间环化反应，得到5,10-二取代基-2,3,7,8-四氰基-5,10-二氢二吡嗪并[2,3- b：2 ′，3′-c]吡嗪11–20。这些化合物具有相当小的分子大小，但是具有强的分子内电荷转移发色体系。它们在溶液中具有很强的荧光，有些甚至在固态也具有荧光，这对于评估其作为电致发光器件的发射器的电致发光性能非常重要。这些新的2,3,7,8-tetracyano-5,10-dihy-drodipyrazino [2,3- b：2′3′- e的物理，结构和电子性质使用紫外-可见光谱和Pariser-Parr-Pople分子轨道计算方法研究了对吡嗪。

  DOI：

  10.1002/jhet.5570340251
• 作为产物：
  描述：

  1,4,5,6-四氢-5,6-二氧-2,3-吡嗪二甲腈 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 2-anilino-3-chloro-5,6-dicyanopyrazine
  参考文献：
  名称：

  通过一锅钯催化的水中偶联反应/环化反应，高效合成5,6-二取代-5 H-吡咯并[2,3 - b ]吡嗪-2,3-二腈

  摘要：

  提出了高效的一锅法合成5,6-二取代-5 H-吡咯并[2,3 - b ]吡嗪-2,3-二碳腈。在水中存在表面活性剂SDS的情况下，在Pd-Cu催化下，5-（烷基-芳基氨基）-6-氯吡嗪-2,3-二腈与苯乙炔的反应可制得所需的产品。高产。

  DOI：

  10.1016/j.tetlet.2012.04.016

文献信息

• Syntheses and spectral properties of 2,3,7,8-tetracyano-5,10-dihydrodipyrazino[2,3-<i>b</i>:2′,3′-<i>e</i>]pyrazine
  作者：Jae-Yun Jaung、Koushi Fukunishi、Masaru Matsuoka

  DOI：10.1002/jhet.5570340251

  日期：1997.3

  10-dihydrodipyrazino[2,3-b:2′,3′-c]pyrazines 11–20. These compounds have rather small molecular size but have strong intramolecular charge-transfer chromophoric system. They have strong fluorescence in solution and some have fluorescence even in the solid state which are very important to evaluate their electroluminescence property as an emitter for electroluminescence devices. The physical, structural, and

  对2-氨基-3-氯-5,6-二氰基吡嗪进行碱催化的分子间环化反应，得到5,10-二取代基-2,3,7,8-四氰基-5,10-二氢二吡嗪并[2,3- b：2 ′，3′-c]吡嗪11–20。这些化合物具有相当小的分子大小，但是具有强的分子内电荷转移发色体系。它们在溶液中具有很强的荧光，有些甚至在固态也具有荧光，这对于评估其作为电致发光器件的发射器的电致发光性能非常重要。这些新的2,3,7,8-tetracyano-5,10-dihy-drodipyrazino [2,3- b：2′3′- e的物理，结构和电子性质使用紫外-可见光谱和Pariser-Parr-Pople分子轨道计算方法研究了对吡嗪。
• Transition-Metal-Free C–N Cross-Coupling Enabled by a Multifunctional Reagent
  作者：Patrick S. Fier、Suhong Kim

  DOI：10.1021/jacs.4c00871

  日期：2024.3.13

  cross-coupling reaction of phenols and primary amines using a simple and readily available multifunctional reagent. The reactions work by induced proximity and electronic activation of both the nucleophile and the electrophile for net dehydrative C–N coupling reactions. Notably, the reactions do not involve the use of a transition metal for C–N bond formation, preactivation of the phenol electrophile, or exclusion

  我们报告了使用简单且易于获得的多功能试剂设计和开发了酚和伯胺的无过渡金属交叉偶联反应。该反应通过亲核试剂和亲电子试剂的诱导接近和电子激活来进行净脱水 C-N 偶联反应。值得注意的是，这些反应不涉及使用过渡金属形成 C-N 键、酚亲电子试剂的预活化或排除空气或湿气。温和的条件可以耐受多种官能团，并使其能够应用于具有多种偶联伙伴的复杂底物的后期功能化。
• NITROGEN-CONTAINING HETEROCYCLIC DERIVATIVE AND ORGANIC ELECTROLUMINESCENCE ELEMENT USING NITROGEN-CONTAINING HETEROCYCLIC DERIVATIVE
  申请人：Yamamoto Hiroshi

  公开号：US20110248251A1

  公开（公告）日：2011-10-13

  Provided are a nitrogen-containing heterocyclic derivative having a specific structure containing a pyrazine skeleton in the center thereof, a hole injecting material or hole transporting material for an organic electroluminescence (EL) device, a light emitting material for an organic EL device, and an electron injecting material or electron transporting material for an organic EL device each containing the nitrogen-containing heterocyclic derivative, an organic EL device which includes one or a plurality of organic layers interposed between a cathode and an anode and in which at least one layer of the organic layers contains the nitrogen-containing heterocyclic derivative, and an apparatus including the organic EL device. The organic EL device shows high luminous brightness and high luminous efficiency even at a low voltage as compared with a conventional device.
• Highly efficient synthesis of 5,6-disubstituted-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles through a one-pot palladium-catalyzed coupling reaction/cyclization in water
  作者：Ali Keivanloo、Mohammad Bakherad、Hossein Nasr-Isfahani、Somayeh Esmaily

  DOI：10.1016/j.tetlet.2012.04.016

  日期：2012.6

  A highly efficient one-pot synthesis of 5,6-disubstituted-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles is presented. The reaction of 5-(alkyl-arylamino)-6-chloropyrazine-2,3-dicarbonitriles with phenylacetylene, catalyzed by Pd–Cu, in the presence of SDS as the surfactant in water, leads to the desired products in good-to-high yields.

  提出了高效的一锅法合成5,6-二取代-5 H-吡咯并[2,3 - b ]吡嗪-2,3-二碳腈。在水中存在表面活性剂SDS的情况下，在Pd-Cu催化下，5-（烷基-芳基氨基）-6-氯吡嗪-2,3-二腈与苯乙炔的反应可制得所需的产品。高产。
• Synthesis and Electrochemical Study of a TCAA Derivative – A potential bipolar redox-active material
  作者：Tino Hagemann、Jan Winsberg、Andreas Wild、Ulrich S. Schubert

  DOI：10.1016/j.electacta.2017.01.055

  日期：2017.2

  The 2,3,7,8-tetracyano-1,4,5,6,9,10-hexazaanthracene (TCAA) derivatives represent an interesting substance class for future research on organic electronic devices, such as solar cells, organic batteries or redox-flow batteries (RFBs). Because of their multivalent redox behavior they are potentially "bipolar", usable both as cathode and anode activ charge-storage materials. Furthermore, they show a strong absorption and fluorescence behavior both in solution and solid state, rendering them a promising emitter for electroluminescence devices, like lamps or displays. In order to evaluate a TCAA for electrochemical applications the derivative 2,3,7,8-tetracyano-5,10-diphenyl-5,10-dihydrodipyrazino [2,3-b:2',3'-e]pyrazine (2) was synthesized in two straightforward synthesis steps. The electrochemical behavior of 2 was initially determined by density functional theory (DFT) calculation and afterwards investigated via rotating disc electrode (RDE), UV-vis-NIR spectroelectrochemical as well as cyclic voltammetry (CV) measurements. It features a quasi-reversible oxidation and re-reduction at E-1/2 = 1.42 V vs. Fc(+)/Fc with a peak split of 96 mV and a quasi-reversible reduction and re-oxidation at E-1/2 =-1.49 V vs. Fc(+)/Fc with a peak split of 174 mV, which lead to a theoretical potential difference of 2.91 V. (C) 2017 Elsevier Ltd. All rights reserved.