3,5-dimethyl-6-propyl-2(1H)-pyrazinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3,5-dimethyl-6-propyl-2(1H)-pyrazinone
• 英文别名: 3,5-dimethyl-6-propyl-1H-pyrazin-2-one
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: GWLWZLSLEQLJJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-己二酮 、 DL-天冬酰胺一水物 以 水 为溶剂， 反应 1.0h， 生成 3,6-dimethyl-5-propyl-2(1H)-pyrazinone 、 3,5-dimethyl-6-propyl-2(1H)-pyrazinone
  参考文献：
  名称：

  3-Methyl-2(1H)-pyrazinones, the Asparagine-Specific Maillard Products Formed from Asparagine and Monosaccharides

  摘要：

  Four unknown compounds from the reactions of monosaccharides and asparagine have been positively identified by spectroscopic elucidation and synthesis-as 3,5-dimethyl-6-ethyl-2(1H)-pyrazinone, 3,6-dimethyl-5-ethyl-2(1H)-pyrazinone, 3,5,6-trimethyl-2(1H)-pyrazinone, and 3-methyl-5,6-diethyl-2(1H)-pyrazinone, which are novel to model reaction studies. This group of compounds can be recognized as asparagine-specific Maillard products. The formation mechanism of them has been proposed. Basically, 3-aminosuccinimide, asparagine, and isoasparagine may be at an equilibrium state. Condensation of isoasparagine and alpha-dicarbonyls (the degradation products of the monosaccharide) leads to the formation of 3-(carboxymethyl)-5,6-dialkyl-2(1H)-pyrazinones, decarboxylation of which generates 3-methyl-5,6-dialkyl-2(1H)-pyrazinones. Identification of this group of compounds from Maillard reaction was herein reported for the first time in literature.

  DOI：

  10.1021/jf00051a040

文献信息

• US5962662A
  申请人：——

  公开号：US5962662A

  公开（公告）日：1999-10-05
• 3-Methyl-2(1H)-pyrazinones, the Asparagine-Specific Maillard Products Formed from Asparagine and Monosaccharides
  作者：Chi-Kuen Shu、Brian M. Lawrence

  DOI：10.1021/jf00051a040

  日期：1995.3

  Four unknown compounds from the reactions of monosaccharides and asparagine have been positively identified by spectroscopic elucidation and synthesis-as 3,5-dimethyl-6-ethyl-2(1H)-pyrazinone, 3,6-dimethyl-5-ethyl-2(1H)-pyrazinone, 3,5,6-trimethyl-2(1H)-pyrazinone, and 3-methyl-5,6-diethyl-2(1H)-pyrazinone, which are novel to model reaction studies. This group of compounds can be recognized as asparagine-specific Maillard products. The formation mechanism of them has been proposed. Basically, 3-aminosuccinimide, asparagine, and isoasparagine may be at an equilibrium state. Condensation of isoasparagine and alpha-dicarbonyls (the degradation products of the monosaccharide) leads to the formation of 3-(carboxymethyl)-5,6-dialkyl-2(1H)-pyrazinones, decarboxylation of which generates 3-methyl-5,6-dialkyl-2(1H)-pyrazinones. Identification of this group of compounds from Maillard reaction was herein reported for the first time in literature.