3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline | 108905-67-5

• 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: 3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline
• 英文别名: 3,8-Dimethyl-2-methylsulfanylimidazo(4,5-f)quinoxaline；3,8-dimethyl-2-methylsulfanylimidazo[4,5-f]quinoxaline
• CAS: 108905-67-5
• 化学式: C₁₂H₁₂N₄S
• 分子量: 244.32
• InChiKey: ZAIKDJJNOQHFDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline 在 palladium on activated charcoal potassium permanganate 、 ammonium formate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 141.75h， 生成 2-氨基-3,8-二甲基咪唑并[4,5-f]喹恶啉
  参考文献：
  名称：

  Regiospecific synthesis of the aminoimidazoquinoxaline (IQx) mutagens from cooked foods

  摘要：

  A versatile regiospecific synthesis has been developed to prepare the six dimethyl- and trimethyl-substituted 2-aminoimidazoquinoxaline (IQx) regioisomers 35, 36, 37, 38, 39, and 40 for complete and unambiguous characterization. The key reaction step in the synthetic sequence for these angular tricycles is a photodehydrohalogenative cyclization of suitably substituted pyrazinylimidazolylethylene intermediates derived from common pyrazine and fully functionalized imidazole precursors. The reaction sequence developed allows for versatility in the substitution pattern as well as total regioisomeric control for the synthesis of all possible methyl and polymethyl analogues of IQx. Comparison of the physical properties among the isomeric di- and trimethyl-IQx's has established the value of unambiguous regiospecific synthesis for structural assignments in this food mutagen series.

  DOI：

  10.1021/jo00031a017
• 作为产物：
  描述：

  2-(5-methyl-2-pyrazinyl)-1-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)ethene 在 potassium tert-butylate 作用下， 以 叔丁醇 、 苯 为溶剂， 反应 0.17h， 以68%的产率得到3,8-dimethyl-2-(methylthio)-imidazo<4,5-f>quinoxaline
  参考文献：
  名称：

  Regiospecific synthesis of the aminoimidazoquinoxaline (IQx) mutagens from cooked foods

  摘要：

  A versatile regiospecific synthesis has been developed to prepare the six dimethyl- and trimethyl-substituted 2-aminoimidazoquinoxaline (IQx) regioisomers 35, 36, 37, 38, 39, and 40 for complete and unambiguous characterization. The key reaction step in the synthetic sequence for these angular tricycles is a photodehydrohalogenative cyclization of suitably substituted pyrazinylimidazolylethylene intermediates derived from common pyrazine and fully functionalized imidazole precursors. The reaction sequence developed allows for versatility in the substitution pattern as well as total regioisomeric control for the synthesis of all possible methyl and polymethyl analogues of IQx. Comparison of the physical properties among the isomeric di- and trimethyl-IQx's has established the value of unambiguous regiospecific synthesis for structural assignments in this food mutagen series.

  DOI：

  10.1021/jo00031a017