1'R,2'S,5'R-menthyl r-2R-methoxycarbonyl-2-phenyl-c-5R-(3'-pyrridyl)pyrrolidine-c-4S-carboxylate | 167417-81-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1'R,2'S,5'R-menthyl r-2R-methoxycarbonyl-2-phenyl-c-5R-(3'-pyrridyl)pyrrolidine-c-4S-carboxylate
• CAS: 167417-81-4
• 化学式: C₂₈H₃₆N₂O₄
• 分子量: 464.605
• InChiKey: ZGQDPQUUKGKCON-LXGQBTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.52
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1'R,2'S,5'R-menthyl r-2R-methoxycarbonyl-2-phenyl-c-5R-(3'-pyrridyl)pyrrolidine-c-4S-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 4.0h， 生成 1'R,2'S,5'R-menthyl r-2R-methoxycarbonyl-2-phenyl-c-5R-(1'-propyl-1',2',5',6'-tetrahydropyrid-3'-yl)pyrrolidine-c-4S-carboxylate
  参考文献：
  名称：

  X=Y−ZH compounds as potential 1,3-dipoles. Part 43. Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl acrylate

  摘要：

  Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt(3) X-Ray crystal structures of representative cycloadducts establish that the absolute configuration of the newly established pyrrolidine stereocentres is independent of the metal salt and the size of the pyrrolidineC(2)-substituent for a series of aryl and aliphatic imines.

  DOI：

  10.1016/0040-4020(94)00940-v
• 作为产物：
  描述：

  (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 在 magnesium sulfate 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 22.0h， 生成 1'R,2'S,5'R-menthyl r-2R-methoxycarbonyl-2-phenyl-c-5R-(3'-pyrridyl)pyrrolidine-c-4S-carboxylate
  参考文献：
  名称：

  X=Y−ZH compounds as potential 1,3-dipoles. Part 43. Metal ion catalysed asymmetric 1,3-dipolar cycloaddition reactions of imines and menthyl acrylate

  摘要：

  Metallo-azomethine ylides, generated from imines by the action of amine bases in combination with LiBr or AgOAc, undergo cycloaddition with both 1R, 2S, 5R- and 1S, 2R, 5S-menthyl acrylate at room temperature to give homochiral pyrrolidines in excellent yield. The stronger the base the faster the cycloaddition and the greater the yield with: 2-t-butyl-1,1,3,3-tetramethylguanidine > DBU > NEt(3) X-Ray crystal structures of representative cycloadducts establish that the absolute configuration of the newly established pyrrolidine stereocentres is independent of the metal salt and the size of the pyrrolidineC(2)-substituent for a series of aryl and aliphatic imines.

  DOI：

  10.1016/0040-4020(94)00940-v