(4S)-4-ethyl-2-(3-methylimidazol-4-yl)-5-oxooxolane-3-carbonyl chloride | 1026950-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4S)-4-ethyl-2-(3-methylimidazol-4-yl)-5-oxooxolane-3-carbonyl chloride
• CAS: 1026950-98-0
• 化学式: C₁₁H₁₃ClN₂O₃
• 分子量: 256.689
• InChiKey: QAJDVNDOFFIFDP-GVWIPJJGSA-N

物化性质

• 沸点：
  491.8±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-4-ethyl-2-(3-methylimidazol-4-yl)-5-oxooxolane-3-carbonyl chloride 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 ammonium formate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.17h， 生成 毛果芸香碱
  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 草酰氯 、 银 、 氯化二乙基铝 、 N,N-二甲基甲酰胺 、 copper(I) bromide 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 24.67h， 生成 (4S)-4-ethyl-2-(3-methylimidazol-4-yl)-5-oxooxolane-3-carbonyl chloride
  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

文献信息

• An effective chirospecific synthesis of (+)-pilocarpine from L-aspartic acid
  作者：Jeffrey M. Dener、Lin Hua Zhang、Henry Rapoport

  DOI：10.1021/jo00057a031

  日期：1993.2

  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).