2,3-bis(3-methoxyphenyl)quinoxaline

• 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: 2,3-bis(3-methoxyphenyl)quinoxaline
• 化学式: C₂₂H₁₈N₂O₂
• 分子量: 342.397
• InChiKey: ITCIMZSMEKXXFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-bis(3-methoxyphenyl)quinoxaline 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-[3-(3-Hydroxyphenyl)quinoxalin-2-yl]phenol
  参考文献：
  名称：

  Synthesis and evaluation of quinoxaline derivatives as potential influenza NS1A protein inhibitors

  摘要：

  A library of quinoxaline derivatives were prepared to target non-structural protein 1 of influenza A (NS1A) as a means to develop anti-influenza drug leads. An in vitro fluorescence polarization assay demonstrated that these compounds disrupted the dsRNA-NS1A interaction to varying extents. Changes of substituent at positions 2, 3 and 6 on the quinoxaline ring led to variance in responses. The most active compounds (35 and 44) had IC50 values in the range of low micromolar concentration without exhibiting significant dsRNA intercalation. Compound 44 was able to inhibit influenza A/Udorn/72 virus growth. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.042
• 作为产物：
  描述：

  3-甲氧基苯乙烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 叔丁基过氧化氢 、 四丁基碘化铵 、 溶剂黄146 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 4.5h， 生成 2,3-bis(3-methoxyphenyl)quinoxaline
  参考文献：
  名称：

  辅助串联催化交叉复分解-氧化：在一个烧瓶中，从苯乙烯到1,2-二酮，再到喹喔啉

  摘要：

  通过结合交叉复分解和Ru催化的烯烃氧化至辅助串联催化序列，由苯乙烯合成1,2-二酮。合成依赖于仅使用一种易位预催化剂，该预催化剂通过加入烷基氢过氧化物作为化学触发剂和氧化剂而原位转化为氧化催化剂。通过氧化产物与邻苯二胺的缩合，一个烧瓶的序列可以扩展到1,2-二酮以外的喹喔啉。

  DOI：

  10.1021/jo4005684

文献信息

• Graphite catalyzed green synthesis of quinoxalines
  作者：Hari K. Kadam、Salman Khan、Rupesh A. Kunkalkar、Santosh G. Tilve

  DOI：10.1016/j.tetlet.2012.12.041

  日期：2013.2

  A new simple approach using environmentally benign, cheap, and easily recyclable graphite as a heterogeneous catalyst for the synthesis of quinoxalines is described. A library of pharmacologically interesting diphenylquinoxalines is prepared by the double condensation of substituted benzils, phenanthrene-9,10-dione, and benzoin with aromatic diamines in 71–93% yields at room temperature in ethanol

  描述了一种使用环境友好，廉价且易于回收的石墨作为多相催化剂合成喹喔啉的简单方法。通过在室温下在乙醇中以71-93％的收率将取代的苯，菲-9,10-二酮和安息香与芳香族二胺进行双缩合，制得一个具有药理学意义的二苯基喹喔啉文库。脂肪族二胺以72-92％的产率从取代的苯甲醚中生成相应的二氢吡嗪。
• Cobalt‐Catalyzed Annulation of <i>o</i>‐Phenylenediamines and Internal Alkynes: Efficient Synthesis of Quinoxaline Derivatives
  作者：Rui Zhao、Ling Wu、Si‐Wei Chen、Zhen Cui、Xu‐Hua Hu、Hui‐Ru Yang、Hongfei Ye、Chun‐Bao Miao、Xun‐Xiang Guo

  DOI：10.1002/ejoc.202300919

  日期：2024.1.15

  A cobalt-catalyzed annulation of o-phenylenediamines and internal alkynes for the synthesis of quinoxalines is reported. This method provides a series of quinoxalines in good to high yields under a simple and mild reaction conditions.

  报道了用于合成喹喔啉的钴催化邻苯二胺和内炔环化。该方法在简单温和的反应条件下以良好至高的收率提供了一系列喹喔啉。
• NaOH-Mediated Direct Synthesis of Quinoxalines from <i>o</i>-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy
  作者：Yan-Bing Wang、Linlin Shi、Xiaojie Zhang、Lian-Rong Fu、Weinan Hu、Wenjing Zhang、Xinju Zhu、Xin-Qi Hao、Mao-Ping Song

  DOI：10.1021/acs.joc.0c02453

  日期：2021.1.1

  A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.
• Khorramabadi-Zad, Ahmad; Azadmanesh, Mohammad; Mohammadi, Somaye, South African Journal of Chemistry, 2013, vol. 66, p. 113 - 116
  作者：Khorramabadi-Zad, Ahmad、Azadmanesh, Mohammad、Mohammadi, Somaye

  DOI：——

  日期：——
• Assisted Tandem Catalytic Cross Metathesis–Oxidation: In One Flask from Styrenes to 1,2-Diketones and Further to Quinoxalines
  作者：Bernd Schmidt、Stefan Krehl、Sylvia Hauke

  DOI：10.1021/jo4005684

  日期：2013.6.7

  synthesized from styrenes by combining a cross metathesis and a Ru-catalyzed alkene oxidation to an assisted tandem catalytic sequence. The synthesis relies on the use of just one metathesis precatalyst, which was in situ converted to the oxidation catalyst by addition of an alkyl hydroperoxide as a chemical trigger and oxidant. The one-flask sequence can be extended beyond 1,2-diketones to quinoxalines, by

  通过结合交叉复分解和Ru催化的烯烃氧化至辅助串联催化序列，由苯乙烯合成1,2-二酮。合成依赖于仅使用一种易位预催化剂，该预催化剂通过加入烷基氢过氧化物作为化学触发剂和氧化剂而原位转化为氧化催化剂。通过氧化产物与邻苯二胺的缩合，一个烧瓶的序列可以扩展到1,2-二酮以外的喹喔啉。