(2S,5S)-5-benzyl-7a-(tert-butyldimethylsilyl)oxy-6,7-dimethyl-2-phenyltetrahydropyrrolo[2,1-b]oxazol-3-one | 606971-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2S,5S)-5-benzyl-7a-(tert-butyldimethylsilyl)oxy-6,7-dimethyl-2-phenyltetrahydropyrrolo[2,1-b]oxazol-3-one
• 英文别名: (2S,5S)-5-benzyl-7a-[tert-butyl(dimethyl)silyl]oxy-6,7-dimethyl-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-b][1,3]oxazol-3-one
• CAS: 606971-07-7
• 化学式: C₂₇H₃₇NO₃Si
• 分子量: 451.681
• InChiKey: GUESBLCYFCLJTL-ATWMZKOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,5S)-5-benzyl-7a-(tert-butyldimethylsilyl)oxy-6,7-dimethyl-2-phenyltetrahydropyrrolo[2,1-b]oxazol-3-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(5S)-5-benzyl-3,4-dimethylpyrrolidin-2-one
  参考文献：
  名称：

  Oxyoxazolidinone as an auxiliary for heterocyclic synthesis. Enantioselective formation of N-unprotected 2-pyrrolidones from selenocarboxylate and allylamines via radical cyclization

  摘要：

  Optic ally active N-unprotected 2-pyrrolidones were prepared in a highly stereoselective manner through radical cyclization reaction of oxyoxazolidinone. Asymmetric induction from the oxyoxazolidinone ring system was generally high and oxazabicyclo[3.3.0]-octanones were obtained in good yields. Treatment of the bicyclic compounds with TBAF resulted in the one-step cleavage of C-O and C-N bond. directly giving secondary 2-pyrrolidones in good yields along with recovery of chiral mandelic acid without loss of optical purity. The use of the present procedure gave optically active 4,5-disubstituted N-unprotected 2-pyrrolidone derivatives trans selectively. (C) 2003 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)01015-9
• 作为产物：
  描述：

  (5S)-N-(1-(S)-benzylallyl)-2-(tert-butyldimethylsilyl)oxy-2-(1-bromo)propionyl-5-phenyl-1,3-oxazolidin-4-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以87%的产率得到(2S,5S)-5-benzyl-7a-(tert-butyldimethylsilyl)oxy-6,7-dimethyl-2-phenyltetrahydropyrrolo[2,1-b]oxazol-3-one
  参考文献：
  名称：

  Oxyoxazolidinone as an auxiliary for heterocyclic synthesis. Enantioselective formation of N-unprotected 2-pyrrolidones from selenocarboxylate and allylamines via radical cyclization

  摘要：

  Optic ally active N-unprotected 2-pyrrolidones were prepared in a highly stereoselective manner through radical cyclization reaction of oxyoxazolidinone. Asymmetric induction from the oxyoxazolidinone ring system was generally high and oxazabicyclo[3.3.0]-octanones were obtained in good yields. Treatment of the bicyclic compounds with TBAF resulted in the one-step cleavage of C-O and C-N bond. directly giving secondary 2-pyrrolidones in good yields along with recovery of chiral mandelic acid without loss of optical purity. The use of the present procedure gave optically active 4,5-disubstituted N-unprotected 2-pyrrolidone derivatives trans selectively. (C) 2003 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)01015-9