<2-(S),3-(S),3'-(S),4-(S),5-(R)>-2,4-dicarbomethoxy-3-(1-hydroxyethyl)-5-phenylpyrrolidine | 139334-54-6

• 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: <2-(S),3-(S),3'-(S),4-(S),5-(R)>-2,4-dicarbomethoxy-3-(1-hydroxyethyl)-5-phenylpyrrolidine
• 英文别名: (2-(S),3-(S),3'-(S),4-(S),5-(R))-2,4-dicarbomethoxy-3-(1-hydroxyethyl)-5-phenylpyrrolidine；dimethyl (2S,3S,4S,5R)-3-[(1S)-1-hydroxyethyl]-5-phenylpyrrolidine-2,4-dicarboxylate
• CAS: 139334-54-6
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: OPYOLINLRSAQFQ-YGTGSIHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 <2-(S),3-(S),3'-(S),4-(S),5-(R)>-2,4-dicarbomethoxy-3-(1-hydroxyethyl)-5-phenylpyrrolidine 在 silver(l) oxide 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (2S,3S,4S,5R)-1-Benzyl-3-((S)-1-benzyloxy-ethyl)-5-phenyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  1,3-dipolar cycloaddition reactions of azomethine ylides on enantiomerically pure (E)-γ-alkoxy-α,β-unsaturated esters.

  摘要：

  Enantiomerically pure (E)-gamma-alkoxy-alpha,beta-unsaturated esters were reacted with azomethine ylides obtained from glycine imines in the presence of LiBr and diazabicycloundecene (DBU), to afford tetrasubstituted pyrrolidines with complete regiocontrol and fair to excellent diastereoselectivity (only two diastereoisomers formed in up to 96: 4 diastereoisomeric ratio). The results are compared with those of other 1,3-dipolar cycloadditions, and the origin of stereocontrol is discussed.

  DOI：

  10.1016/s0957-4166(00)80030-0
• 作为产物：
  描述：

  (E)-(S)-4-(tert-butyldimethylsilanyloxy)pent-2-enoic acid methyl ester 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 8.25h， 生成 <2-(S),3-(S),3'-(S),4-(S),5-(R)>-2,4-dicarbomethoxy-3-(1-hydroxyethyl)-5-phenylpyrrolidine
  参考文献：
  名称：

  1,3-dipolar cycloaddition reactions of azomethine ylides on enantiomerically pure (E)-γ-alkoxy-α,β-unsaturated esters.

  摘要：

  Enantiomerically pure (E)-gamma-alkoxy-alpha,beta-unsaturated esters were reacted with azomethine ylides obtained from glycine imines in the presence of LiBr and diazabicycloundecene (DBU), to afford tetrasubstituted pyrrolidines with complete regiocontrol and fair to excellent diastereoselectivity (only two diastereoisomers formed in up to 96: 4 diastereoisomeric ratio). The results are compared with those of other 1,3-dipolar cycloadditions, and the origin of stereocontrol is discussed.

  DOI：

  10.1016/s0957-4166(00)80030-0

文献信息

• 1,3-dipolar cycloaddition reactions of azomethine ylides on enantiomerically pure (E)-γ-alkoxy-α,β-unsaturated esters.
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Laura Raimondi、Tullio Pilati

  DOI：10.1016/s0957-4166(00)80030-0

  日期：1991.1

  Enantiomerically pure (E)-gamma-alkoxy-alpha,beta-unsaturated esters were reacted with azomethine ylides obtained from glycine imines in the presence of LiBr and diazabicycloundecene (DBU), to afford tetrasubstituted pyrrolidines with complete regiocontrol and fair to excellent diastereoselectivity (only two diastereoisomers formed in up to 96: 4 diastereoisomeric ratio). The results are compared with those of other 1,3-dipolar cycloadditions, and the origin of stereocontrol is discussed.