甲喹酮杂质2 | 61522-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 甲喹酮杂质2
• 英文名称: 2-Acetyl-3-methylquinoxaline 1-Oxide
• 英文别名: 4-desoxymaquindox；N4-deoxymequindox；4-deoxymequindox；4-desoxymequinox；1-(3-methyl-1-oxy-quinoxalin-2-yl)-ethanone；2-Acetyl-3-methylchinoxalin 1-Oxid；1-(3-methyl-1-oxidoquinoxalin-1-ium-2-yl)ethanone
• CAS: 61522-57-4
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: RPIDSNIUFJODMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲喹酮杂质2 在 溴 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以57%的产率得到2-acetyl-3-(bromomethyl)quinoxaline 1-oxide
  参考文献：
  名称：

  某些3-[（（烷硫基）甲基]喹喔啉]一氧化物衍生物的合成及抗菌活性。

  摘要：

  已经合成了一些3-[（烷硫基）甲基]喹喔啉一氧化物衍生物（1），并筛选了其抗菌活性。发现2-乙酰基-3-[（甲基磺酰基）甲基]喹喔啉1-氧化物（7a）对一些对兽医重要的病原体，包括猪痢疾密螺旋体，是猪痢疾的致病菌，具有良好的体外活性。在体内实验中，该化合物（7a）在21天的时间内完全保护了猪免受猪痢疾的侵害。

  DOI：

  10.1021/jm00362a007
• 作为产物：
  描述：

  乙酰甲喹 在 甲胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 甲喹酮杂质2
  参考文献：
  名称：

  喹烯酮四种代谢产物的化学合成方法

  摘要：

  本发明涉及喹烯酮四种主要代谢物脱二氧喹烯酮，脱二氧喹烯酮侧链羰基还原产物，N1-脱氧喹烯酮和N4-脱氧喹烯酮侧链羰基还原产物的合成方法。脱二氧喹烯酮的合成是以连二亚硫酸钠对乙酰甲喹脱氧，生成中间体脱二氧乙酰甲喹，再与苯甲醛缩合，得脱二氧喹烯酮。接着以硼氢化钠对其侧链羰基进行还原，得脱二氧喹烯酮侧链羰基还原产物。以亚磷酸三甲酯对乙酰甲喹选择性脱氧生成N1-脱氧乙酰甲喹，与苯甲醛缩合，得N1-脱氧喹烯酮。用合适的胺对乙酰甲喹选择性脱氧生成N1-脱氧乙酰甲喹，与苯甲醛缩合，得N1-脱氧喹烯酮，以硼氢化钠对其侧链的羰基还原，得N4-脱氧喹烯酮侧链羰基还原产物。

  公开号：

  CN103420926B

文献信息

• Reactions of 2-Acetyl-3-methylquinoxaline 1,4-Dioxide and Its Derivatives
  作者：Katsuhide Matoba、Takashi Terada、Masaru Sugiura、Takao Yamazaki

  DOI：10.3987/r-1987-01-0055

  日期：——
• Convenient synthesis of quinocetone metabolites: Characterization, theoretical investigation, and cytotoxicity study
  作者：Jiaheng Zhang、Linxia Li、Yubo Li、Bing Peng、Songqing Li、Zhiqiang Zhou、Haixiang Gao、Suxia Zhang

  DOI：10.1016/j.molstruc.2012.04.071

  日期：2012.8

  Quinocetone (3-methyl-2-quinoxalinbenzenevinylketo-1,4-dioxide; QCT) is a new promising antimicrobial growth promoter for quinoxalines. The identification of the major metabolites of QCT has resulted in a number of studies regarding its metabolic pathway. However, little is known about the systematic synthesis, characterization, and simultaneous determination of its metabolites. To obtain system data for the four main metabolites of QCT, a convenient synthesis of these compounds was performed. All synthesized compounds were characterized by infrared spectroscopy, nuclear magnetic resonance, and high-resolution mass spectroscopy. The theoretical N-O bond dissociation enthalpies (BDEs) and octanol-water partition coefficient (K-ow) were estimated. A cytotoxicity assay for these compounds in hepatocytes isolated from rats was proposed, and the cytotoxicity results were evaluated based on the calculated N-O BDEs. (C) 2012 Elsevier B.V. All rights reserved.
• Formation of quinoxaline monoxides from reaction of benzofurazan oxide with enones and carbon-13 NMR correlations of quinoxaline N-oxides
  作者：Arthur F. Kluge、Michael L. Maddox、Graham S. Lewis

  DOI：10.1021/jo01298a030

  日期：1980.5
• Synthesis, mass spectral characterization, NMR analyses, and DFT calculations of 1-desoxymaquindox and 4-desoxymaquindox
  作者：Jiaheng Zhang、Qingrong Peng、Suxia Zhang、Yubo Li、Songqing Li、Haixiang Gao、Zhiqiang Zhou

  DOI：10.1016/j.molstruc.2010.11.057

  日期：2011.2

  Maquindox, 3-methyl-2-acetylquinoxaline-1,4-dioxide, is a quinoxaline-N,N-dioxide used in veterinary medicine as a feed additive. 1-Desoxymaquindox and 4-desoxymaquindox, two novel deoxidized metabolites of maquindox are synthesized from their parent drug. This study deals with the structural and spectral properties of the maquindox metabolites by employing experimental and theoretical methods. The investigation, using ultra-performance liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry, shows independent proof of the structures. Gauge-including atomic orbital NMR chemical shifts are calculated for isomeric quinoxaline metabolite pairs and several different parameters (correlation coefficient, mean absolute error, and corrected mean absolute error) are investigated. Comparison of the experimental and calculated H-1 and C-13 NMR chemical shifts allows the reliable assignment of the isomeric quinoxaline compound pairs. (C) 2010 Elsevier B.V. All rights reserved.
• MATOBA KATSUHIDE; TERADA TAKASHI; SUGIURA MASARU; YAMAZAKI TAKAO, HETEROCYCLES, 26!,(1987) N 1, 55-58
  作者：MATOBA KATSUHIDE、 TERADA TAKASHI、 SUGIURA MASARU、 YAMAZAKI TAKAO

  DOI：——

  日期：——