6-乙酰基-2-(羟基甲基)-2,3-二氢-4(1H)-吡啶酮 | 214218-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-乙酰基-2-(羟基甲基)-2,3-二氢-4(1H)-吡啶酮
• 英文名称: 2-acetyl-6-(hydroxymethyl)-5,6-dihydro-4H-pyridinone
• 英文别名: 2-acetyl-5-hydroxymethyl-5,6-dihydro-4H-pyridinone；6-Acetyl-2,3-dihydro-2-(hydroxymethyl)-4(1H)-pyridinone；6-acetyl-2-(hydroxymethyl)-2,3-dihydro-1H-pyridin-4-one
• CAS: 214218-63-0
• 化学式: C₈H₁₁NO₃
• 分子量: 169.18
• InChiKey: SIWHSHNFBDSUFB-UHFFFAOYSA-N

物化性质

• 沸点：
  371.8±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

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：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-吡喃木糖 、 L-赖氨酸 以 水 为溶剂， 反应 6.0h， 生成 2-<(2-furyl)methylidene>-4-hydroxy-5-methyl-2H-furan-3-one 、 6-乙酰基-2-(羟基甲基)-2,3-二氢-4(1H)-吡啶酮
  参考文献：
  名称：

  Identification of New Heterocyclic Nitrogen Compounds from Glucose-Lysine and Xylose-Lysine Maillard Model Systems

  摘要：

  Aqueous sugar (glucose or xylose)-lysine model systems were heated at 80 degreesC for 6 h with the pH maintained at a predetermined value (3, 4, or 5). Selected compounds were isolated by combinations of solvent extraction and semipreparative HPLC, prior to identification by NMR and mass spectrometry. Two compounds were identified from the pH 5 glucose system and were identified as epsilon-[2-formyl-5-(hydroxymethyl)pyrrole-1-yl]-L-norleucine (pyrraline) and the new compound, 1-(5-carboxy-5-aminopentyl)-2-formyl-3-(1,2,3 -trihydroxypropyl)pyrrole. A third compound was partially characterized. 2-Acetyl-5-hydroxymethyl-5,6-dihydro-4H-pyridinone was identified in the pH 3 xylose system, and the new compound, 8-furan-2-yl-methyl-5-hydroxymethyl-5,6 dione, was identified in the pH 4 xylose system. 2-Furfurylidene-4-hydroxy-5-methyl-3(2H) was identified in both xylose systems. Mechanisms of formation are proposed for the novel compounds.

  DOI：

  10.1021/jf000722+

文献信息

• Analysis of Furanone, Pyranone, and New Heterocyclic Colored Compounds from Sugar−Glycine Model Maillard Systems
  作者：Jennifer M. Ames、Richard G. Bailey、John Mann

  DOI：10.1021/jf980528b

  日期：1999.2.1

  experiments, as the related compounds 4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone and 2, 3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone. The remaining compound from the glucose system and the colorless compound from the xylose system were identified as 5-(hydroxymethyl)furfural and 4-hydroxy-5-methyl-3(2H)-furanone, respectively.

  将含水糖（木糖或葡萄糖）-甘氨酸模型系统回流2小时，pH保持在5。总反应产物的反相HPLC给出了木糖系统的两个已分离峰（其中一个是有色的），五个已分离的峰葡萄糖系统的峰（其中两个是有色的）。通过半制备HPLC从乙酸乙酯提取物中分离出负责这些峰的组分。主要使用NMR，将木糖系统中的有色化合物鉴定为新的2-乙酰基-6-（羟甲基）-5,6-二氢-4H-吡啶酮。来自葡萄糖系统的有色化合物最有可能是相关新化合物2-乙酰基-6-羟基-7-（羟甲基）-1,5,6,7-四氢-4H-的两个新的顺式/反式环异构体azepinone + ++。这些化合物是从糖-氨基酸模型系统中分离出来的第一个单环结构，据报道是有色的。主要通过NMR实验确定了葡萄糖系统中的两个无色成分，分别为相关化合物4-羟基-2-（羟甲基）-5-甲基-3（2H）-呋喃酮和2，3-二氢-3， 5-二羟基-6-甲基-4H-吡喃酮。来自葡萄糖系统的
• Identification of New Heterocyclic Nitrogen Compounds from Glucose-Lysine and Xylose-Lysine Maillard Model Systems
  作者：Richard G. Bailey、Jennifer M. Ames、John Mann

  DOI：10.1021/jf000722+

  日期：2000.12.1

  Aqueous sugar (glucose or xylose)-lysine model systems were heated at 80 degreesC for 6 h with the pH maintained at a predetermined value (3, 4, or 5). Selected compounds were isolated by combinations of solvent extraction and semipreparative HPLC, prior to identification by NMR and mass spectrometry. Two compounds were identified from the pH 5 glucose system and were identified as epsilon-[2-formyl-5-(hydroxymethyl)pyrrole-1-yl]-L-norleucine (pyrraline) and the new compound, 1-(5-carboxy-5-aminopentyl)-2-formyl-3-(1,2,3 -trihydroxypropyl)pyrrole. A third compound was partially characterized. 2-Acetyl-5-hydroxymethyl-5,6-dihydro-4H-pyridinone was identified in the pH 3 xylose system, and the new compound, 8-furan-2-yl-methyl-5-hydroxymethyl-5,6 dione, was identified in the pH 4 xylose system. 2-Furfurylidene-4-hydroxy-5-methyl-3(2H) was identified in both xylose systems. Mechanisms of formation are proposed for the novel compounds.