2,3-diethyl-5,8-bis(4-methoxyphenyl)-6,7-dinitroquinoxaline

• 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-diethyl-5,8-bis(4-methoxyphenyl)-6,7-dinitroquinoxaline
• 英文别名: 2,3-Diethyl-5,8-bis(4-methoxyphenyl)-6,7-dinitroquinoxaline
• 化学式: C₂₆H₂₄N₄O₆
• 分子量: 488.5
• InChiKey: GTHAELZLWMUMIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,4-己二酮 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 三甲基乙酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 2,3-diethyl-5,8-bis(4-methoxyphenyl)-6,7-dinitroquinoxaline
  参考文献：
  名称：

  C–H-Activated Direct Arylation of Strong Benzothiadiazole and Quinoxaline-Based Electron Acceptors

  摘要：

  Electron acceptors are important components of p-conjugated materials, but the strong electron-withdrawing properties of the required synthetic intermediates often make them poor substrates in synthetic schemes designed around conventional organometallic cross-coupling. Here, strong benzodiimine-based acceptors, including 5,6-difluoro[2,1,3]benzothiadiazole, 5,6-dicyano[2,1,3]benzothiadiazole, 5,6-dicyanobenzo[d][1,2,3]triazole, 6,7-dicyanoquinoxaline, and 6,7-dinitroquinoxaline, are shown to undergo facile palladium-catalyzed C-H direct arylation with a variety of bromoarenes in moderate to high yields. The electrochemical characteristics of di-2-thienyl derivatives synthesized using this methodology are compared and suggest that, in an electron-transfer sense, 5,6-dicyano[2,1,3]benzothiadiazole is a comparably strong acceptor to benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole. The synthetic results suggest that high electron-withdrawing ability, which has traditionally limited reaction yields and structural variety in organic electronic materials, may be advantageous when employing C-H activated direct arylation in certain circumstances.

  DOI：

  10.1021/acs.joc.5b02551

文献信息

• MATERIALS HAVING ELECTRON DEFICIENT MOIETIES AND METHODS OF SYNTHESIZING THEREOF
  申请人：Georgia Tech Research Corporation

  公开号：US20150218115A1

  公开（公告）日：2015-08-06

  Various materials and polymers having electron deficient moieties and methods of synthesizing thereof are described herein. Specifically, a C—H bond activation method is disclosed wherein an electron deficient group having one or more activated C—H bonds is coupled to one or more aryl groups to afford materials or polymers which may be used in organic electronic and photonic applications.

  本文描述了具有电子亏损基团的各种材料和聚合物，以及它们的合成方法。具体来说，披露了一种C-H键活化方法，其中具有一个或多个活化的C-H键的电子亏损基团与一个或多个芳基偶联，以获得可用于有机电子和光子应用的材料或聚合物。
• US9315477B2
  申请人：——

  公开号：US9315477B2

  公开（公告）日：2016-04-19
• C–H-Activated Direct Arylation of Strong Benzothiadiazole and Quinoxaline-Based Electron Acceptors
  作者：Junxiang Zhang、Timothy C. Parker、Wayne Chen、LaRita Williams、Victor N. Khrustalev、Evgheni V. Jucov、Stephen Barlow、Tatiana V. Timofeeva、Seth R. Marder

  DOI：10.1021/acs.joc.5b02551

  日期：2016.1.15

  Electron acceptors are important components of p-conjugated materials, but the strong electron-withdrawing properties of the required synthetic intermediates often make them poor substrates in synthetic schemes designed around conventional organometallic cross-coupling. Here, strong benzodiimine-based acceptors, including 5,6-difluoro[2,1,3]benzothiadiazole, 5,6-dicyano[2,1,3]benzothiadiazole, 5,6-dicyanobenzo[d][1,2,3]triazole, 6,7-dicyanoquinoxaline, and 6,7-dinitroquinoxaline, are shown to undergo facile palladium-catalyzed C-H direct arylation with a variety of bromoarenes in moderate to high yields. The electrochemical characteristics of di-2-thienyl derivatives synthesized using this methodology are compared and suggest that, in an electron-transfer sense, 5,6-dicyano[2,1,3]benzothiadiazole is a comparably strong acceptor to benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole. The synthetic results suggest that high electron-withdrawing ability, which has traditionally limited reaction yields and structural variety in organic electronic materials, may be advantageous when employing C-H activated direct arylation in certain circumstances.