甲喹诺克斯杂质1 | 61522-56-3

• 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: 甲喹诺克斯杂质1
• 英文名称: 3-Acetyl-2-methylquinoxaline 1-Oxide
• 英文别名: mequindox-4-monoxide；1-desoxymaquindox；N1-deoxymequindox；1-deoxymequindox；1-desoxymequinox；N1-desoxymequindox；2-Acetyl-3-methylquinoxaline 4-oxide；1-(3-methyl-4-oxidoquinoxalin-4-ium-2-yl)ethanone
• CAS: 61522-56-3
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: KKJLJOBEYXZTCY-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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  乙酰甲喹	3-methyl-2-acetylquinoxaline-1,4-dioxide	13297-17-1	C11H10N2O3	218.212
  1-(3-甲基喹喔啉-2-基)乙酮	2-methyl-3-acetylquinoxaline	22059-64-9	C11H10N2O	186.213

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	1-(3-methyl-4-oxy-quinoxalin-2-yl)-ethanone (toluene-4-sulfonyl)-hydrazone	67452-58-8	C18H18N4O3S	370.432

反应信息

• 作为反应物：
  描述：

  甲喹诺克斯杂质1 、 苯甲醛 在 二乙胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以8.73 g的产率得到2-cinnamoyl-3-methylquinoxaline 4-oxide
  参考文献：
  名称：

  Convenient synthesis of quinocetone metabolites: Characterization, theoretical investigation, and cytotoxicity study

  摘要：

  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.

  DOI：

  10.1016/j.molstruc.2012.04.071
• 作为产物：
  描述：

  1-(3-甲基喹喔啉-2-基)乙酮 在 sodium tungstate 、 双氧水 作用下， 以 溶剂黄146 为溶剂， 以52.6%的产率得到甲喹诺克斯杂质1
  参考文献：
  名称：

  Reactions of 2-Acetyl-3-methylquinoxaline 1,4-Dioxide and Its Derivatives

  摘要：

  DOI：

  10.3987/r-1987-01-0055

文献信息

• 1,4-Dioxo- and 4-oxoquinoxaline-2-carboxaldehyde sulfonylhydrazones and
  申请人：Pfizer Inc.

  公开号：US04100284A1

  公开（公告）日：1978-07-11

  The invention relates to novel chemical compounds which have useful antibacterial properties and are also of value in promoting animal growth and improving animal feed efficiency. More specifically, these new chemical compounds are certain sulfonylhydrazones of 1,4-dioxoquinoxaline-2-carboxaldehyde, 4-oxoquinoxaline-2-carboxaldehyde and certain derivatives thereof of formula (I): ##STR1## wherein A is N or N .fwdarw. O; R is a member selected from the group consisting of alkyl having from one to five carbon atoms, trifluoromethyl, phenyl, npahthyl, benzyl, styryl and phenyl substituted by up to two members selected from the group consisting of Cl, F, Br, CH.sub.3, CH.sub.3 O and NO.sub.2 ; R.sup.1 is hydrogen or methyl; R.sup.2 is hydrogen or methyl; R.sup.3 is a 6- or 7-position substituent and is selected from the group H, Cl, CH.sub.3, CH.sub.3 O, SO.sub.2 NH.sub.2, SO.sub.2 NHCH.sub.3 and SO.sub.2 N(CH.sub.3).sub.2 ; R.sup.4 is a 7- or 6-position substituent and is selected from the group H, Cl and CH.sub.3 ; with the proviso that when R.sup.4 is Cl or CH.sub.3, R.sup.3 and R.sup.4 are the same.

  该发明涉及具有有用的抗菌性能的新型化合物，同时在促进动物生长和改善动物饲料效率方面也具有价值。更具体地说，这些新的化合物是1,4-二氧化喹啉-2-羧醛的某些磺基脒酮，4-氧喹啉-2-羧醛及其某些衍生物的化合物，其化学式为(I)：##STR1## 其中A为N或N→O；R为从含有一至五个碳原子的烷基、三氟甲基、苯基、萘基、苄基、苯乙烯基和苯基中选择的一种成员；R1为氢或甲基；R2为氢或甲基；R3为6-或7-位置取代基，选择自H、Cl、CH3、CH3O、SO2NH2、SO2NHCH3和SO2N(CH3)2的群组中；R4为7-或6-位置取代基，选择自H、Cl和CH3的群组中；但当R4为Cl或CH3时，R3和R4相同。
• 喹烯酮四种代谢产物的化学合成方法
  申请人：华中农业大学

  公开号：CN103420926B

  公开（公告）日：2016-05-11

  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。
• Landquist; Stacey, Journal of the Chemical Society, 1953, p. 2822,2827
  作者：Landquist、Stacey

  DOI：——

  日期：——
• 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.