3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one | 263715-90-8

• 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: 3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one
• 英文别名: 3-Chloro-7-methoxy-1-methylquinoxalin-2-one
• CAS: 263715-90-8
• 化学式: C₁₀H₉ClN₂O₂
• 分子量: 224.647
• InChiKey: LBVQSHYSAYCSIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one 在 喹啉 、 Pd-BaSO₄ 四(三苯基膦)钯 、 氢气 、 potassium acetate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (E)-7-methoxy-1-methyl-3-(4-methoxycarbonyl)styrylquinoxalin-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
• 作为产物：
  描述：

  5-甲氧基-N-甲基-1,2-苯二胺 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one
  参考文献：
  名称：

  1,2,4-Triazolo[4,3-a]quinoxaline-1,4-diones as antiallergic agents

  摘要：

  A series of new 1,4-dihydro-1,2,4-triazolo[4,3-]quinoxaline-1,4-diones has been prepared. These compounds were tested as inhibitors of antigen-induced release of histamine (AIR) in vitro from rat peritoneal mast cells (RMC) and as inhibitors of IgE-mediated rat passive cutaneous anaphylaxis (PCA). Most of this new class of antiallergic agents showed good activity in the RMC and PCA tests. The most potent compound, 2-acetyl-7-chloro-5-n-propyl-1,2,4-triazolo[4,3-a]quinoxaline-1,4-dione (1x), with an I50 value of 0.1 microM, is 30 times more potent than disodium cromoglycate (DSCG) in the RMC assay.

  DOI：

  10.1021/jm00381a016

文献信息

• LOEV, B.;MUSSER, J. H.;BROWN, R. E.;JONES, H.;KAHEN, R.;HUANG, FU-CHIH;KH+, J. MED. CHEM., 1985, 28, N 3, 363-366
  作者：LOEV, B.、MUSSER, J. H.、BROWN, R. E.、JONES, H.、KAHEN, R.、HUANG, FU-CHIH、KH+

  DOI：——

  日期：——
• 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.
• 1,2,4-Triazolo[4,3-a]quinoxaline-1,4-diones as antiallergic agents
  作者：Bernard Loev、John H. Musser、Richard E. Brown、Howard Jones、Robert Kahen、Fu Chih Huang、Atul Khandwala、Paula Sonnino-Goldman、Mitchell J. Leibowitz

  DOI：10.1021/jm00381a016

  日期：1985.3

  A series of new 1,4-dihydro-1,2,4-triazolo[4,3-]quinoxaline-1,4-diones has been prepared. These compounds were tested as inhibitors of antigen-induced release of histamine (AIR) in vitro from rat peritoneal mast cells (RMC) and as inhibitors of IgE-mediated rat passive cutaneous anaphylaxis (PCA). Most of this new class of antiallergic agents showed good activity in the RMC and PCA tests. The most potent compound, 2-acetyl-7-chloro-5-n-propyl-1,2,4-triazolo[4,3-a]quinoxaline-1,4-dione (1x), with an I50 value of 0.1 microM, is 30 times more potent than disodium cromoglycate (DSCG) in the RMC assay.