(S)-(+)-O-bromoacetyl-N-allylmandelamide | 492435-19-5

• 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: (S)-(+)-O-bromoacetyl-N-allylmandelamide
• 英文别名: [(1S)-2-oxo-1-phenyl-2-(prop-2-enylamino)ethyl] 2-bromoacetate
• CAS: 492435-19-5
• 化学式: C₁₃H₁₄BrNO₃
• 分子量: 312.163
• InChiKey: JICOAMABXDXKDA-LBPRGKRZSA-N

物化性质

• 沸点：
  462.2±45.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-O-bromoacetyl-N-allylmandelamide 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 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 (2R,5S)-N-allyl-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
• 作为产物：
  描述：

  (2S,5S)-N-allyl-2-(tert-butyldimethylsilyl)oxy-2-bromomethyl-5-phenyl-1,3-oxazolidin-4-one 在 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 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.5h， 生成 (S)-(+)-O-bromoacetyl-N-allylmandelamide
  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

• Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones and an efficient synthesis of optically active secondary 2-pyrrolidones
  作者：Yoji Omata、Akikazu Kakehi、Masashi Shirai、Akio Kamimura

  DOI：10.1016/s0040-4039(02)01632-5

  日期：2002.9

  Treatment of (−)-O-acyllactamides or mandelamides with TBSOTf in the presence of base gives optically active 2-oxy-1,3-oxazolidin-4-ones stereoselectively, which serve as useful precursors for the preparation of optically active secondary 2-pyrrolidones via radical cyclization and subsequent one-step removal of mandelic acid.

  在碱存在下，用TBSOTf处理（-）- O-酰基酰胺或扁桃酰胺，可以立体选择性地产生旋光的2-氧基-1,3-恶唑烷丁-4-酮，它们可用作制备旋光的仲2-羟基的有用前体。吡咯烷酮通过自由基环化和随后的一步去除扁桃酸的步骤。