2-benzoyl-3-methyl-6,7-dimethylqinoxaline 1,4-dioxide | 60680-33-3

• 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-benzoyl-3-methyl-6,7-dimethylqinoxaline 1,4-dioxide
• 英文别名: 2-benzoyl-3,6,7-trimethylquinoxaline 1,4-dioxide；phenyl-(3,6,7-trimethyl-1,4-dioxy-quinoxalin-2-yl)-methanone；Phenyl-(3,6,7-trimethyl-1,4-dioxido-quinoxaline-1,4-diium-2-yl)methanone；phenyl-(3,6,7-trimethyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)methanone
• CAS: 60680-33-3
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: XCSPIAAQYDKAFA-UHFFFAOYSA-N

物化性质

• 熔点：
  227-228 °C(Solv: methanol (67-56-1))
• 沸点：
  526.5±60.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-methyl-6,7-dimethylqinoxaline 1,4-dioxide 以15%的产率得到
  参考文献：
  名称：

  JARRAR A. A.; HALAWI S. S.; HADDADIN M. J., HETEROCYCLES, 1976, 4, NO 6, 1077-1082

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-二甲基-1-氧代-2,1,3-苯并恶二唑-1-鎓 、 1-苯基-1,3-丁二酮 在 3 A molecular sieve 作用下， 反应 24.0h， 以88%的产率得到2-benzoyl-3-methyl-6,7-dimethylqinoxaline 1,4-dioxide
  参考文献：
  名称：

  由4,5（6,7）-二甲基苯并呋喃恶烷合成喹喔啉1,4-二氧化物

  摘要：

  在这项研究中，由新型取代的苯并呋喃喃合成了新型取代的喹喔啉1,4-二氧化物。通过2，3-二甲基-6-硝基苯叠氮化物2的热分解来制备4，5（6，7）-二甲基苯并呋喃3。使用化合物3和硅胶或分子筛催化的1,3-二酮4的烯醇形式获得了新型喹喔啉1,4-二氧化物衍生物。这些反应得到异构体喹喔啉1，4-二氧化物5和6。化合物3的这些反应可涉及固体催化剂表面上的互变异构体4，5-二甲基苯并呋喃3a，6，7-二甲基苯并呋喃3b。

  DOI：

  10.1002/jhet.5570330410

文献信息

• The reactions of benzofuroxan with carbonyl compounds on the surface of solid catalysts
  作者：Tohru Takabatake、Yumiko Hasegawa、Minoru Hasegawa

  DOI：10.1002/jhet.5570300602

  日期：1993.12

  The cyclocondensations of benzofuroxan 1a with carbonyl compounds were smoothly and efficiently carried out by the adsorption of the components on the surface of silica gel or a molecular sieve to form a 2,3-disubstituted quinoxaline 1,4-dioxide. When the reactions using a molecular sieve 3A (powder) were carried out at 90°, the actual reaction times were reduced to 0.5-2 hours. Although Duerckheimer

  通过将组分吸附在硅胶或分子筛的表面上以形成2，3-二取代的喹喔啉1，4-二氧化物，苯并呋喃喃1a与羰基化合物的环缩反应可以平稳有效地进行。当在90°下使用分子筛3A（粉末）进行反应时，实际反应时间减少到0.5-2小时。尽管Duerckheimer报告了当使5-甲氧基苯并呋喃1e与乙酰乙酸乙酯2j反应时仅分离出7-取代的喹喔啉1,4-二氧化物，但通过我们的方法，它仅生成了6-甲氧基异构体作为反应产物。5-羧基苯并呋喃聚糖1f不与羰基化合物反应。
• Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents
  作者：Andrés Jaso、Belén Zarranz、Ignacio Aldana、Antonio Monge

  DOI：10.1016/s0223-5234(03)00137-5

  日期：2003.9

  A series of 2-acetyl and 2-benzoyl-6(7)-substituted quinoxaline 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. The results show that 2-acetyl-3-methylquinoxaline 1,4-di-N-oxide derivatives with chlorine, methyl or methoxy group in position 7 of the benzene moiety (compounds 2, 4 and 6, respectively) and unsubstituted (3) have good antitubercular activity, exhibiting EC90/MIC values between 0.80 and 4.29. In conclusion, the potency, selectivity and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Photocyclisation of 2-aroylquinoxalines; formation of coloured indolo[l,2-a]quinoxalines
  作者：Adnan Atfah、Muhammad Y.、Abu-Shuheil、John Hill

  DOI：10.1016/s0040-4020(01)96016-8

  日期：1990.1
• Synthesis of Quinoxaline 1,4-Dioxides from Benzofuroxan Proceeds Not in, But on Zeolite
  作者：Tohru Takabatake、Hiroyasu Ito、Aki Takei、Tomoyuki Miyazawa、Minoru Hasegawa、Shinichi Miyairi

  DOI：10.3987/com-02-9661

  日期：——

  Quinoxaline synthesis using Na-zeolite A as a catalyst to proceeds in a better yield than that using zeolite X. The pore diameter of zeolite X is large enough to allow the benzofuroxan derivatives access to cages, therefore part of benzofuroxan is adsorbed in the internal surface of zeolite X. Whereas the windows to the cages of Na-zeolite A are too small to allow the benzofuroxan derivatives access to the cages, therefore all the benzofuroxan is adsorbed on the external surface of zeolite. The reactions of benzofuroxans with benzoylacetone was catalyzed by zeolite proceed not in, but on zeolite.