3-hydroxy-4-methyl-5-(¹³C)methyl(5-¹³C)furan-2(5H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-hydroxy-4-methyl-5-(¹³C)methyl(5-¹³C)furan-2(5H)-one
• 英文别名: 4,5-Dimethyl-3-hydroxy-2(5H)-furanone-13C2；4-hydroxy-3-methyl-2-(113C)methyl-(213C)2H-furan-5-one
• 化学式: C₆H₈O₃
• 分子量: 130.106
• InChiKey: UNYNVICDCJHOPO-NDLBAUGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙醛-13C2 、 草酰丙酸二乙酯 在 吡啶 、 盐酸 、 溶剂黄146 作用下， 生成 3-hydroxy-4-methyl-5-(¹³C)methyl(5-¹³C)furan-2(5H)-one
  参考文献：
  名称：

  Formation of 3-Hydroxy-4,5-dimethyl-2(5H)-furanone (Sotolone) from 4-Hydroxy-l-isoleucine and 3-Amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone

  摘要：

  The proposed formation of 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone) from 4-hydroxy-L-isoleucine (1) and the corresponding lactone 3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone (2) by thermally induced oxidative deamination was corroborated. The formation of sotolone was studied in model systems by reacting 1 or 2 with different carbonyl compounds in a phosphate buffer at pH 5 at 100 degrees C for 1 h. The amount of sotolone was quantified by stable isotope dilution assays using C-13(2)-labeled sotolone as internal standard and GC-MS operating in the selected ion monitoring mode. In general, alpha-ketoaldehydes were found to be more reactive than alpha-diketones. Methylglyoxal gave rise to about 64 mu g sotolone per mg 1 (7.4 mol %) compared to less than 1 mu g (<0.1 mol %) when reacted with 2,3-pentanedione. Using 2 as the starting material, the yields were increased to 274 mu g (35.9 mol %) and 5.4 mu g (0.7 mol %), respectively. The optimum pH of the reaction with HIL was 5, representing the best compromise between the lactonization step and the amino-carbonyl reaction. Significant amounts of sotolone were generated only at temperatures higher than 70 degrees C. The yield increased over a period of 10 h to about 210 mu g/mg 1 (23.8 mol %). The Strecker degradation of 1, resulting in 3-hydroxy-2-methylbutanal, was a competitive reaction to the formation of sotolone.

  DOI：

  10.1021/jf9506702