6-fluoro-2,3-diphenylquinoxaline

• 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: 6-fluoro-2,3-diphenylquinoxaline
• 化学式: C₂₀H₁₃FN₂
• mdl: MFCD02935067
• 分子量: 300.335
• InChiKey: UDTBCTBYTUDBRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5',6,6'-四羟基-3,3,3',3'-四甲基-1,1'-螺旋联吲哚 、 6-fluoro-2,3-diphenylquinoxaline 生成 2,3-diphenyl-6-[[5',6,6'-tris[(2,3-diphenylquinoxalin-6-yl)oxy]-1,1,1',1'-tetramethyl-3,3'-spirobi[2H-indene]-5-yl]oxy]quinoxaline
  参考文献：
  名称：

  Efficient screening of electron transport material in multi-layer organic light emitting diodes by combinatorial methods

  摘要：

  采用有机分子气相沉积和掩模技术相结合的方法，在一块基板上制备了49个具有不同结构和层厚度的有机发光二极管（OLED）矩阵。制备了一个景观库，其中包含两个正交的线性渐变发射器和阻挡电子传输材料，位于厚度恒定的空穴传输层之上。该实验旨在研究附加电子传输材料对效率的影响。使用半自动测量装置，评估了49个OLED的器件参数。实验证实，ITO/TPD/Alq3/Al双层器件存在最佳Alq3层厚度，且在最佳Alq3层上添加额外的阻挡层无法改善这种优化的双层结构。然而，通过用Alq3/螺喹啉层的特定组合代替最佳Alq3层厚度，可以提高光度效率。

  DOI：

  10.1039/a809256g
• 作为产物：
  描述：

  4-氟-2-硝基苯胺 在 一水合肼 作用下， 以 neat (no solvent) 为溶剂， 反应 8.0h， 生成 6-fluoro-2,3-diphenylquinoxaline
  参考文献：
  名称：

  Graphene oxide (GO) or reduced graphene oxide (rGO): efficient catalysts for one-pot metal-free synthesis of quinoxalines from 2-nitroaniline

  摘要：

  A straightforward one-pot preparation of library of quinoxalines from 2-nitroanilines under entirely metal-free conditions is described. Initial reduction of nitroaniline with hydrazine hydrate is efficiently catalyzed by graphene oxide (GO) or reduced graphene oxide (rGO), and further one-pot tandem reactions with 1,2-dicarbonyl compounds or with alpha-hydroxy ketones afford quinoxalines in excellent yields. The catalyst is recovered, characterized, and found to be recyclable for consecutive four runs examined with appreciable conversions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.065

文献信息

• A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
  作者：Vakhid A. Mamedov、Nataliya A. Zhukova、Victor V. Syakaev、Aidar T. Gubaidullin、Tat'yana N. Beschastnova、Dil'bar I. Adgamova、Aida I. Samigullina、Shamil K. Latypov

  DOI：10.1016/j.tet.2012.10.045

  日期：2013.1

  A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange

  基于3-（苯并咪唑-2-基）喹喔啉-2（1 H）-与1,2-的环收缩，已开发出一种高效且通用的具有两个苯并咪唑片段的喹喔啉衍生物的合成方法。二氨基苯及其各种类型的取代和稠合衍生物。由于分子间和分子内过程，涉及桥联和相邻碳原子的大多数双-苯并咪唑基喹喔啉信号的几种形式之间的自缔合，质子交换，构象和/或互变异构交换，且NMR光谱中的苯并咪唑片段变宽。苯并咪唑片段与分子的喹喔啉核心之间的共轭作用比喹喔啉衍生物（10c）与其噻二唑[ f ]-（17）和吡咯并[ a ]-（19）环化了衍生物，导致整个分子的平面度更大。
• Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles
  作者：Jiajun Wu、Christophe Darcel

  DOI：10.1021/acs.joc.0c02505

  日期：2021.1.1

  A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30–91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64–72% yields when the

  使用铁催化剂通过氢转移方法有效地开发了用各种醇直接和选择性还原硝基芳烃的方法。该方案专门导致亚胺的产率为30-91％，并具有良好的官能团耐受性。值得注意的是，从邻硝基苯胺衍生物开始，在醇存在下，当与其他氧化剂DDQ进行反应时，苯并咪唑的收率可达64-72％，由28- 96％的产率。这种方法在亚胺的铁中是前所未有的，也为制备喹喔啉和苯并咪唑提供了可持续的替代方法。
• <scp>l</scp>-Proline mediated synthesis of quinoxalines; evaluation of cytotoxic and antimicrobial activity
  作者：Ahmed Kamal、Korrapati Suresh Babu、Shaikh Faazil、S. M. Ali Hussaini、Anver Basha Shaik

  DOI：10.1039/c4ra08615e

  日期：——

  A simple, greener and highly efficient method for the synthesis of functionalized quinoxalines has been developed employingl-proline as a catalyst in water. The newly synthesized quinoxaline–sulphonamide conjugates exhibited significant cytotoxic and antimicrobial activities.

  已开发出一种简单、更环保且高效的方法，利用l-脯氨酸作为水中催化剂合成官能化喹啉。新合成的喹啉-磺胺酰胺共轭物表现出显著的细胞毒性和抗微生物活性。
• First Example of Quinoxaline-Directed C-H Activation: A Novel Method for Acetoxylation of Arenes
  作者：B. Reddy、K. Ramesh、J. Yadav

  DOI：10.1055/s-0030-1259292

  日期：2011.1

  2-Aryl- and 2,3-diarylquinoxalines undergo smooth acetoxylation in the presence of 5 mol% Pd(OAc)2 and a stoichiometric amount of PhI(OAc)2 via C-H activation to produce the corresponding acetoxy-susbstituted quinoxaline derivatives in excellent yields with high regioselectivity.

  2-芳基和2,3-二芳基喹喔啉在5 mol% Pd(OAc)2存在下，通过C-H活化与等摩尔量的PhI(OAc)2进行平稳的乙酰氧基化反应，以高产率和高区域选择性生成相应的乙酰氧基取代喹喔啉衍生物。
• Quinoxaline as an integrated directing group in palladium-catalyzed <i>ortho</i>-C–H bond arylation of the aryl unit of 2-arylquinoxalines
  作者：Imane Idris、Fazia Derridj、Thierry Roisnel、Henri Doucet、Jean-François Soulé

  DOI：10.1039/c8nj02713g

  日期：——

  We report the Pd-catalyzed C–H bond arylation at the ortho-position of the aryl unit of 2-arylquinoxalines. The reaction proceeds with complete regioselectivity using phosphine-free Pd(OAc)2 as the catalyst and potassium acetate as inexpensive base. In contrast to previously employed directing groups, quinoxaline is an integrated directing group in the final product that only promotes ortho-mono-arylation

  我们报道了在2-芳基喹喔啉芳基单元的邻位上钯催化的CH键芳基化。使用无膦的Pd（OAc）2作为催化剂，乙酸钾作为廉价的碱，以完全的区域选择性进行反应。与先前采用的导向基团相反，喹喔啉是最终产物中的整合导向基团，其仅促进邻-单芳基化而不形成双芳基化产物。已经成功地使用了多种（杂）芳基溴化物，包括溴吡啶衍生物。