tert-butyl-3-oxo-3-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)propanoate | 138407-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl-3-oxo-3-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)propanoate
• 英文别名: 1H-Imidazole-5-propanoic acid, 4-bromo-1-methyl-2-(methylthio)-beta-oxo-, 1,1-dimethylethyl ester；tert-butyl 3-(5-bromo-3-methyl-2-methylsulfanylimidazol-4-yl)-3-oxopropanoate
• CAS: 138407-31-5
• 化学式: C₁₂H₁₇BrN₂O₃S
• 分子量: 349.249
• InChiKey: IAHTWHWOKIRNLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  86.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-3-oxo-3-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)propanoate 在 三氟乙酸 作用下， 反应 24.0h， 以99%的产率得到5-acetyl-4-bromo-1-methyl-2-methylthioimidazole
  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：

  醋酸叔丁酯 、 Methyl 4-bromo-1-methyl-2-methylthio-5-imidazolecarboxylate 在 lithium methanolate 、 lithium diisopropyl amide 作用下， 生成 tert-butyl-3-oxo-3-(4-bromo-1-methyl-2-(methylthio)-5-imidazolyl)propanoate
  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