1-Butyl-4-(α-D-erythrofuranosyl)-3-pyrrolecarbaldehyde | 142890-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Butyl-4-(α-D-erythrofuranosyl)-3-pyrrolecarbaldehyde
• CAS: 142890-82-2
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: NRKKKDRXWVZFBV-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.69
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1--1-deoxy-D-fructose 以 重水 为溶剂， 反应 1.0h， 生成 1-Butyl-4-(D-arabino-tetritol-1-yl)-3-pyrrolecarbaldehyde 、 1-Butyl-3-(D-arabino-tetritol-1'-yl)-4-pyridone 、 1-Butyl-4-(β-D-erythrofuranosyl)-3-pyrrolecarbaldehyde 、 1-Butyl-4-(α-D-erythrofuranosyl)-3-pyrrolecarbaldehyde
  参考文献：
  名称：

  Influence of malondialdehyde on the Maillard degradation of Amadori compounds

  摘要：

  1-Amino-1-deoxy-D-fructose (7), and its N-butyl derivative (8), reacted with malondialdehyde to yield the 1-deoxy-1-(3-oxo-1-propenylamino)-D-fructoses 9 and 10, respectively. Small proportions of 4-methyl-1,4-dihydro-3,5-pyridinedicarbaldehyde (12) and 1-deoxy-1-(3.5-diformyl-4-methyl-1,4-dihydro-pyridin-1-yl)-D-fructose (14) were also formed in the reaction with 7, and of 1-butyl-4-methyl-1,4-dihydro-3,5-pyridinedicarbaldehyde (13) in the reaction with 8. The reaction of 7 with methylmalondialdehyde afforded 1-deoxy-1-(2-methyl-3-oxo-1-propenylamino)-D-fructose (11). The enaminals 9 and 10 cyclised, in neutral or weakly alkaline aqueous solution, into a mixture of 4-(D-arabino-tetritol-1-yl)-3-pyrrolecarbaldehyde pyrrolecarbaldehyde (15 and 17, respectively) and 3-(D-arabino-tetritol-1-yl)-4-pyridone (19 and 21, respectively). Small proportions of 4-(hydroxymethyl)-3-pyrrolecarbaldehyde (16) and 3-(hydroxymethyl)-4-pyridone (20) were also formed in the cyclisation of 9, and of 1-butyl-4-(alpha,beta-D-erythrofuranosyl)-3-pyrrolecarbaldehyde (18-alpha,beta) in the cyclisation of 10. All of the heterocyclic compounds were unstable.

  DOI：

  10.1016/s0008-6215(00)90577-9