(2S,5S,6R)-7a-(tert-butyldimethylsilyl)oxy-5-isopropyl-6-methyl-2-phenyltetrahydropyrrolo[2,1-b]oxazol-3-one | 604783-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2S,5S,6R)-7a-(tert-butyldimethylsilyl)oxy-5-isopropyl-6-methyl-2-phenyltetrahydropyrrolo[2,1-b]oxazol-3-one
• 英文别名: (2S,5S,6R)-7a-[tert-butyl(dimethyl)silyl]oxy-6-methyl-2-phenyl-5-propan-2-yl-6,7-dihydro-5H-pyrrolo[2,1-b][1,3]oxazol-3-one
• CAS: 604783-98-4
• 化学式: C₂₂H₃₅NO₃Si
• 分子量: 389.61
• InChiKey: MYSBSNFAFPOKJN-UXIHHHQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5S,6R)-7a-(tert-butyldimethylsilyl)oxy-5-isopropyl-6-methyl-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77%的产率得到(4R,5S)-5-isopropyl-4-methylpyrrolidin-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：

  (S)-(+)-扁桃酸 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (2S,5S,6R)-7a-(tert-butyldimethylsilyl)oxy-5-isopropyl-6-methyl-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

文献信息

• Oxyoxazolidinone as an auxiliary for heterocyclic synthesis. Enantioselective formation of N-unprotected 2-pyrrolidones from selenocarboxylate and allylamines via radical cyclization
  作者：Akio Kamimura、Yoji Omata、Keiichi Tanaka、Masashi Shirai

  DOI：10.1016/s0040-4020(03)01015-9

  日期：2003.8

  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.