(5S)-N-(1-(R)-benzylallyl)-2-(tert-butyldimethylsilyl)oxy-5-phenyl-2-(phenylseleno)acetyl-1,3-oxazolidin-4-one | 604783-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S)-N-(1-(R)-benzylallyl)-2-(tert-butyldimethylsilyl)oxy-5-phenyl-2-(phenylseleno)acetyl-1,3-oxazolidin-4-one
• 英文别名: (5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-3-[(2R)-1-phenylbut-3-en-2-yl]-2-(phenylselanylmethyl)-1,3-oxazolidin-4-one
• CAS: 604783-92-8
• 化学式: C₃₂H₃₉NO₃SeSi
• 分子量: 592.712
• InChiKey: VJGUQMPPLPXOTE-KONNIWBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 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：

  (5S)-N-(1-(R)-benzylallyl)-2-(tert-butyldimethylsilyl)oxy-5-phenyl-2-(phenylseleno)acetyl-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96%的产率得到(2S,5R,6S)-5-benzyl-7a-(tert-butyldimethylsilyl)oxy-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
• 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 、 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 为溶剂， 反应 12.0h， 生成 (5S)-N-(1-(R)-benzylallyl)-2-(tert-butyldimethylsilyl)oxy-5-phenyl-2-(phenylseleno)acetyl-1,3-oxazolidin-4-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.