2,3-di(o-hydroxyphenylene)quinoxaline | 4196-27-4

• 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-di(o-hydroxyphenylene)quinoxaline
• 英文别名: 2,3-di(2-hydroxyphenyl)quinoxaline；di(hydroxyphenyl)quinoxaline；6,6'-(1,4-Dihydroquinoxaline-2,3-diylidene)di(cyclohexa-2,4-dien-1-one)；2-[3-(2-hydroxyphenyl)quinoxalin-2-yl]phenol
• CAS: 4196-27-4
• 化学式: C₂₀H₁₄N₂O₂
• 分子量: 314.343
• InChiKey: KWHRMGWGMJZQAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 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：
  66.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-di(o-hydroxyphenylene)quinoxaline 在 sodium isopropylate 、 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 4.0h， 以61%的产率得到6-chlorodibenzo[3,4:8,9][1,3,2]dioxaphosphonino[6,7-b]-quinoxaline-6-oxide
  参考文献：
  名称：

  Synthesis of New Benzosubstituted Dioxaphosphonines Containing Quinoxaline Subunit

  摘要：

  A simple and efficient synthesis of previously unknown benzosubstituted dioxaphosphonines containing a quinoxaline subunit is described. Reasonably good yields of the products, mild reaction conditions, and convenient work-up are the advantages of this method. The procedure does not require any catalyst or activator and can be efficiently achieved via dianion cyclization. All the synthesized compounds have been characterized by satisfactory elemental analyses and spectral (IR, 1H, 13C, 31P NMR, and mass) studies. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500903530891
• 作为产物：
  描述：

  1,2-bis(2-methoxyphenyl)ethane-1,2-diol 在 氢溴酸 、 乙硫醇钠 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2,3-di(o-hydroxyphenylene)quinoxaline
  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

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。
• Cyanide-Catalyzed Cyclizations via Aldimine Coupling
  作者：B. Jesse E. Reich、Aaron K. Justice、Brittany T. Beckstead、Joseph H. Reibenspies、Stephen A. Miller

  DOI：10.1021/jo035245j

  日期：2004.2.1

  Aldimine coupling (AIC) is the nitrogen analogue of the benzoin condensation and has been applied to dialdimines, providing the first examples of cyclizations effected by cyanide-catalyzed AIC. Sodium cyanide promoted the facile, intramolecular cyclization of several dialdimines in N,N-dimethylformamide, methanol, or methylene chloride/water (phase-transfer conditions) yielding a variety of six-membered

  醛亚胺偶联（AIC）是安息香缩合反应的氮类似物，已应用于二胺，提供了氰化物催化的AIC进行环化的第一个实例。氰化钠促进了在N，N-二甲基甲酰胺，甲醇或二氯甲烷/水（相转移条件）中几种二胺的易行的分子内环化反应，产生了多种六元杂环。在有氧条件下，发生氧化环化以提供二亚胺杂环。用刚性二甲胺观察到了低聚，其中没有环化作用。
• Synthesis and Characterization of Tris[2,3-di(o-oxyphenylene)quinoxalin]cyclotriphosphazene--A Novel Spiroheterocyclophosphazene
  作者：Abbas Tarassoli、Mohammad Reza Shushizadeh

  DOI：10.1080/10426500307787

  日期：2003.4

  Hexachlorocyclotriphosphazene (NPCl2)(3), reacted with 2,3-di(o-hydroxyphenylene)quinoxalin in the presence of a base, to yield tris[2,3-di(o-oxyphenylene)quinoxalin]cyclotriphosphazene. The synthesis of 2,3-di(o-hydroxy phenylene)quinoxaline was carried out through three steps: benzoin condensation, oxidation, and reaction of diketone with diamine. The products were characterized by (HNMR)-H-1, (PNMR)-P-31, IR, and mass spectral data.
• US4908426A
  申请人：——

  公开号：US4908426A

  公开（公告）日：1990-03-13
• US5010197A
  申请人：——

  公开号：US5010197A

  公开（公告）日：1991-04-23