(2S)-2-ethyl-3-(hydroxymethyl)-4-(3-methylimidazol-4-yl)butanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2S)-2-ethyl-3-(hydroxymethyl)-4-(3-methylimidazol-4-yl)butanoic acid
• 化学式: C₁₁H₁₈N₂O₃
• 分子量: 226.276
• InChiKey: WJRPDGADPABWOY-HTLJXXAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-2-ethyl-3-(hydroxymethyl)-4-(3-methylimidazol-4-yl)butanoic acid 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 毛果芸香碱 、 (-)-isopilocarpine
  参考文献：
  名称：

  An effective chirospecific synthesis of (+)-pilocarpine from L-aspartic acid

  摘要：

  A short and efficient synthesis of (+)-pilocarpine (1) has been accomplished in 10 steps and 51 % overall yield from L-aspartic acid. The synthesis features a diastereoselective alkylation of a protected aspartic acid diester derivative and a selective hydrolysis of the alpha-methyl ester to give the corresponding amino acid. Subsequent replacement of the amino group with bromo, esterification, and a modified Reformatsky reaction with 1-methylimidazole-5-carboxaldehyde (8) afforded imidazole-substituted lactone 28. Details concerning this novel lactone synthesis are also described. Finally, hydrogenolysis of the lactone carbon-oxygen bond and selective reduction of the resulting monoester afforded pure (+)-pilocarpine (1).

  DOI：

  10.1021/jo00057a031
• 作为产物：
  描述：

  (2S,3S)-2-bromo-3-ethylbutane-1,4-dioic acid 1-tert-butyl 4-methyl diester 在 palladium on activated charcoal sodium tetrahydroborate 、 草酰氯 、 银 、 ammonium formate 、 氯化二乙基铝 、 N,N-二甲基甲酰胺 、 copper(I) bromide 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.83h， 生成 (2S)-2-ethyl-3-(hydroxymethyl)-4-(3-methylimidazol-4-yl)butanoic acid
  参考文献：
  名称：

  An effective chirospecific synthesis of (+)-pilocarpine from L-aspartic acid

  摘要：

  A short and efficient synthesis of (+)-pilocarpine (1) has been accomplished in 10 steps and 51 % overall yield from L-aspartic acid. The synthesis features a diastereoselective alkylation of a protected aspartic acid diester derivative and a selective hydrolysis of the alpha-methyl ester to give the corresponding amino acid. Subsequent replacement of the amino group with bromo, esterification, and a modified Reformatsky reaction with 1-methylimidazole-5-carboxaldehyde (8) afforded imidazole-substituted lactone 28. Details concerning this novel lactone synthesis are also described. Finally, hydrogenolysis of the lactone carbon-oxygen bond and selective reduction of the resulting monoester afforded pure (+)-pilocarpine (1).

  DOI：

  10.1021/jo00057a031