diimidazo[1,2-a:2',1'-c]quinoxaline | 756894-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: diimidazo[1,2-a:2',1'-c]quinoxaline
• 英文别名: diimidazo[1,2-a:2′,1′-c]quinoxaline；2,5,8,11-tetrazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),3,5,7,9,12,14-heptaene
• CAS: 756894-15-2
• 化学式: C₁₂H₈N₄
• 分子量: 208.222
• InChiKey: XFHXKNZQKGBXQW-UHFFFAOYSA-N

物化性质

• 熔点：
  260.9-261.4 °C(Solv: hexane (110-54-3); chloroform (67-66-3))
• 沸点：
  325.2±42.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diimidazo[1,2-a:2',1'-c]quinoxaline 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98 %的产率得到3,10-dibromodiimidazo[1,2-a:2',1'-c]quinoxaline
  参考文献：
  名称：

  通过高通量实验探索铜催化的苯乙烯酮和苯乙烯亚胺-炔环加成反应

  摘要：

  高通量实验已用于重新审视铜催化的苯乙烯酮-炔环加成反应。反应得到了改进，并发现了新的点击和释放反应。

  DOI：

  10.1002/chem.202302713
• 作为产物：
  描述：

  1,2-二溴苯 在 copper(I) oxide 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 diimidazo[1,2-a:2',1'-c]quinoxaline
  参考文献：
  名称：

  通过高通量实验探索铜催化的苯乙烯酮和苯乙烯亚胺-炔环加成反应

  摘要：

  高通量实验已用于重新审视铜催化的苯乙烯酮-炔环加成反应。反应得到了改进，并发现了新的点击和释放反应。

  DOI：

  10.1002/chem.202302713

文献信息

• Selective synthesis and optical properties of diimidazo[1,2-a:5′,1′-c]quinoxaline derivatives
  作者：Shoji Matsumoto、Shunsuke Abe、Motohiro Akazome

  DOI：10.1016/j.tet.2019.05.041

  日期：2019.6

  reaction at the 3 position. Focused on the optical properties, a more efficient substituent effect at the 10 position was obtained compared with the analogous structure, diimidazo[1,2-a:2′,1′-c]quinoxaline derivatives. In addition, we revealed that the diimidazo[1,2-a:5′,1′-c]quinoxaline skeleton potentially has an electron-donating character on the optical properties by introducing an electron-withdrawing

  通过Pd催化的1,2-双（2-碘-1 H-咪唑-1-基）苯分子内偶联反应合成了新的二咪唑并[1,2- a：5'，1'- c ]喹喔啉衍生物。该方法用于通过添加硼酸酯选择性地在10位引入芳基取代基。此外，通过在3位的进一步偶联反应可以逐步引入芳基取代基。着眼于光学性质，与类似结构二咪唑并[1,2- a：2'，1'- c ]喹喔啉衍生物相比，在10位上获得了更有效的取代作用。另外，我们发现二咪唑[1,2- a：5'，1'- c通过引入吸电子取代基，]喹喔啉骨架可能在光学性质上具有供电子性。
• Copper(I)-Catalyzed Cycloaddition of 4-Bromosydnones and Alkynes for the Regioselective Synthesis of 1,4,5-Trisubstituted Pyrazoles
  作者：Elodie Decuypere、Simon Specklin、Sandra Gabillet、Davide Audisio、Hui Liu、Lucie Plougastel、Sergii Kolodych、Frédéric Taran

  DOI：10.1021/ol503482a

  日期：2015.1.16

  Copper-catalyzed cycloaddition of alkynes with 4-bromosydnones provides a convenient, mild, and regioselective method for the synthesis of a wide range of bromopyrazoles. The broad functional group tolerance of the cycloaddition reaction and further palladium-catalyzed cross-coupling reactions allowed the preparation of polyfunctionalized 1,4,5-pyrazoles that are otherwise difficult to obtain by conventional

  铜与4-溴丁酮的铜催化环加成反应为合成多种溴吡唑提供了一种方便，温和且区域选择性的方法。环加成反应和进一步的钯催化的交叉偶联反应具有宽泛的官能团耐受性，因此可以制备多官能化的1,4,5-吡唑，否则很难通过常规方法获得。
• Novel formation of diimidazo[1,2-a:2′,1′-c]quinoxaline derivatives and their optical properties
  作者：Shoji Matsumoto、Erdenebolor Batmunkh、Motohiro Akazome、Yoshiyuki Takata、Michiko Tamano

  DOI：10.1039/c1ob06002c

  日期：——

  Reaction of 1,2-di(imidazolyl)benzene treated with n-BuLi proceeded to give diimidazo[1,2-a:2′,1′-c]quinoxaline in the presence of iodine or Pd(PPh3)4. Blue fluorescence was observed from 3,10-diarylated diimidazoquinoxalines with high quantum yield. They were also applied to organic light-emitting devices as emitters, in which the diphenyl derivative emits a nearly pure blue light.

  的反应 1,2-二（咪唑基）苯在碘或Pd（PPh 3）4存在下，用n- BuLi处理的化合物继续生成二咪唑并[1,2- a：2'，1'- c ]喹喔啉。从3,10-二芳基二咪唑并喹喔啉中以高量子产率观察到蓝色荧光。它们还被用作有机发光器件的发光体，其中二苯衍生物发出近乎纯净的蓝光。
• Fluorescence of Diimidazo[1,2-<i>a</i>:2′,1′-<i>c</i>]quinoxalinium Salts Under Various Conditions
  作者：Shoji Matsumoto、Hajime Abe、Motohiro Akazome

  DOI：10.1021/jo302531g

  日期：2013.3.15

  The synthesis and photophysical properties of diimidazo[1,2-a:2',1'-c]quinoxalinium salts were examined for different counteranions. The ethyl-substituted diimidazo[1,2-a:2',1'-c]quinoxalinium salt with tosylate anion (categolized in ionic liquid) showed good fluorescence (Phi(F) = 0.77) in organic solvent. The 3,10-diphenyldiimidazo[1,2-a:2',1'-c]quinoxalinium salts showed absorption and fluorescence peaks resembling those of the former diimidazoquinoxaline. The salt also emitted under various conditions such as in organic solvents, water, and even in the solid state, while retaining a good fluorescence quantum yield (Phi(F) = 0.5-0.8). Furthermore, the fluorescence was quenched efficiently through the introduction of an electron-donating substituent on the alkyl side chain.
• ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC PHOTOELECTRIC APPARATUS THEREOF
  申请人：Shanghai Tianma AM-OLED Co., Ltd

  公开号：US20170186972A1

  公开（公告）日：2017-06-29

  The present disclosure provides a nitrogen-containing heterocyclic compound having a general formula (I) and an organic photoelectric apparatus thereof. The compound of general formula (I) is: wherein A 1 , A 2 , A 3 , and A 4 are independently selected from a hydrogen atom, a function group having a general formula (II); A 1 , A 2 , A 3 , and A 4 include at least one function group having the general formula (II); R 1 and R 2 are independently selected from one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group; Y 1 and Y 2 are independently selected from substituted or non-substituted C and N, the general formula (II) being: wherein X is selected from one of oxyl group (—O—), sulfhydryl group (—S—), substituted or non-substituted imino group, substituted or non-substituted methylene group, and substituted or non-substituted silicylene group; and R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group, and C 2-30 heterocyclic aromatic group.