6-methoxycarbonyl-3-methylquinoxaline-2(1H)-one | 263715-86-2

• 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: 6-methoxycarbonyl-3-methylquinoxaline-2(1H)-one
• 英文别名: methyl 3-methyl-2-oxo-1H-quinoxaline-6-carboxylate
• CAS: 263715-86-2
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: WRKFGCNLJNUYIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxycarbonyl-3-methylquinoxaline-2(1H)-one 在 四(三苯基膦)钯 、 potassium acetate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline
  参考文献：
  名称：

  Synthesis of Quinoxaline Derivatives Bearing the Styryl and Phenylethynyl Groups and Application to a Fluorescence Derivatization Reagent

  摘要：

  The cross-coupling of 2-chloro-6-methoxycarbonyl-3-methylquinoxaline (2) and 3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one (7) with phenylacetylene in the presence of Pd(PPh3)(4) gave 6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline (3) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)phenylethynylquinoxalin-2(1H)-one (9), respectively. Compounds (3 and 9) were further converted into the corresponding olefinic compounds, 6-methoxycarbonyl-3-methyl-2-styrylquinoxaline (4) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)styrylquinoxalin-2(1H)-one (10), by partial hydrogenation on palladium catalysts such as Lindlar catalyst and Pd/BaSO4-quinoline, but the conformation of the resulting olefins was unexpectedly E-form. These quinoxaline derivatives showed fluorescent emission bands at a range from 398 to 467 nm in MeCN when the excitation wavelength of 353-405 nm was applied. Further, 3-(4-chlorocarbonyl)phenylethynyl-7-methoxy-1-methylquinoxalin-2(1H)-one (12) was demonstrated to be applicable to a fluorescence derivatization reagent for amines.

  DOI：

  10.3987/com-99-s61
• 作为产物：
  描述：

  丙酮酸乙酯 、 3,4-二氨基苯甲酸甲酯 以 乙醇 为溶剂， 反应 20.0h， 以45%的产率得到6-methoxycarbonyl-3-methylquinoxaline-2(1H)-one
  参考文献：
  名称：

  Synthesis of Quinoxaline Derivatives Bearing the Styryl and Phenylethynyl Groups and Application to a Fluorescence Derivatization Reagent

  摘要：

  The cross-coupling of 2-chloro-6-methoxycarbonyl-3-methylquinoxaline (2) and 3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one (7) with phenylacetylene in the presence of Pd(PPh3)(4) gave 6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline (3) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)phenylethynylquinoxalin-2(1H)-one (9), respectively. Compounds (3 and 9) were further converted into the corresponding olefinic compounds, 6-methoxycarbonyl-3-methyl-2-styrylquinoxaline (4) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)styrylquinoxalin-2(1H)-one (10), by partial hydrogenation on palladium catalysts such as Lindlar catalyst and Pd/BaSO4-quinoline, but the conformation of the resulting olefins was unexpectedly E-form. These quinoxaline derivatives showed fluorescent emission bands at a range from 398 to 467 nm in MeCN when the excitation wavelength of 353-405 nm was applied. Further, 3-(4-chlorocarbonyl)phenylethynyl-7-methoxy-1-methylquinoxalin-2(1H)-one (12) was demonstrated to be applicable to a fluorescence derivatization reagent for amines.

  DOI：

  10.3987/com-99-s61

文献信息

• [EN] QUINOXALINES AND AZA-QUINOXALINES AS CRTH2 RECEPTOR MODULATORS<br/>[FR] QUINOXALINES ET AZA-QUINOXALINES COMME MODULATEURS DU RÉCEPTEUR CRTH2
  申请人：MERCK SHARP & DOHME

  公开号：WO2012087861A1

  公开（公告）日：2012-06-28

  The invention provides certain quinoxalines and aza-quinoxalines of the Formula (I), and their pharmaceutically acceptable salts, wherein J1, J2, R1, R2, R3, R22, Ra, Rb, Rc, Rd, X, Y, b, n, and q are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions associated with with uncontrolled or inappropriate stimulation of CRTH2 function.

  该发明提供了式（I）中的某些喹喔啉和氮杂喹喔啉，以及它们的药用盐，其中J1、J2、R1、R2、R3、R22、Ra、Rb、Rc、Rd、X、Y、b、n和q如本文所定义。该发明还提供包含这些化合物的药物组合物，以及使用这些化合物治疗与CRTH2功能的不受控制或不适当刺激相关的疾病或症状的方法。
• QUINOXALINES AND AZA-QUINOXALINES AS CRTH2 RECEPTOR MODULATORS
  申请人：Boyce Christopher W.

  公开号：US20130303517A1

  公开（公告）日：2013-11-14

  The invention provides certain quinoxalines and aza-quinoxalines of the Formula (I), and their pharmaceutically acceptable salts, wherein J 1 , J 2 , R 1 , R 2 , R 3 , R 22 , R a , R b , R c , R d , X, Y, b, n, and q are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions associated with uncontrolled or inappropriate stimulation of CRTH 2 function.

  本发明提供了式（I）的某些喹喔啉和氮杂喹喔啉，以及其药学上可接受的盐，其中J1、J2、R1、R2、R3、R22、Ra、Rb、Rc、Rd、X、Y、b、n和q如本文所定义。本发明还提供了包含这些化合物的制药组合物，并使用这些化合物治疗与CRTH2功能不受控制或不适当刺激相关的疾病或病症的方法。
• 6-SUBSTITUTED 2-QUINOLINONES AND 2-QUINOXALINONES AS POLY(ADP-RIBOSE)POLYMERASE INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：EP1709012B1

  公开（公告）日：2015-07-29
• US9469615B2
  申请人：——

  公开号：US9469615B2

  公开（公告）日：2016-10-18
• Synthesis of Quinoxaline Derivatives Bearing the Styryl and Phenylethynyl Groups and Application to a Fluorescence Derivatization Reagent
  作者：Akira Katoh、Tohru Yoshida、Junko Ohkanda

  DOI：10.3987/com-99-s61

  日期：——

  The cross-coupling of 2-chloro-6-methoxycarbonyl-3-methylquinoxaline (2) and 3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one (7) with phenylacetylene in the presence of Pd(PPh3)(4) gave 6-methoxycarbonyl-3-methyl-2-phenylethynylquinoxaline (3) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)phenylethynylquinoxalin-2(1H)-one (9), respectively. Compounds (3 and 9) were further converted into the corresponding olefinic compounds, 6-methoxycarbonyl-3-methyl-2-styrylquinoxaline (4) and 7-methoxy-1-methyl-3-(4-methoxycarbonyl)styrylquinoxalin-2(1H)-one (10), by partial hydrogenation on palladium catalysts such as Lindlar catalyst and Pd/BaSO4-quinoline, but the conformation of the resulting olefins was unexpectedly E-form. These quinoxaline derivatives showed fluorescent emission bands at a range from 398 to 467 nm in MeCN when the excitation wavelength of 353-405 nm was applied. Further, 3-(4-chlorocarbonyl)phenylethynyl-7-methoxy-1-methylquinoxalin-2(1H)-one (12) was demonstrated to be applicable to a fluorescence derivatization reagent for amines.