ethyl (S,E)-4-(2-oxo-4-phenyloxazolidin-3-yl)but-3-enoate | 1101366-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (S,E)-4-(2-oxo-4-phenyloxazolidin-3-yl)but-3-enoate
• 英文别名: (4S)-3-{(E)-3-(ethoxycarbonyl)propenyl}-4-phenyl-2-oxazolidinone；ethyl (E)-4-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]but-3-enoate
• CAS: 1101366-35-1
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: CXSGZRSXKZBRIG-BCRSCGJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (S,E)-4-(2-oxo-4-phenyloxazolidin-3-yl)but-3-enoate 、 N-chloro-N-sodio-tert-butylcarbamate 在 Br^(1-)*C₃₇H₃₇N₂O⁽¹⁺⁾ 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-O-tert-butyl 2-O-ethyl (3S)-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidine-3-carbonyl]aziridine-1,2-dicarboxylate 、 1-O-tert-butyl 2-O-ethyl (3R)-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidine-3-carbonyl]aziridine-1,2-dicarboxylate
  参考文献：
  名称：

  Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with N-Chloro-N-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts

  摘要：

  Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,S,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.

  DOI：

  10.1021/jo2010632
• 作为产物：
  描述：

  (S)-4-phenyl-3-vinyloxazolidin-2-one 、 碘代醋酸乙酯 在 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 苯 为溶剂， 反应 22.0h， 以69%的产率得到ethyl (S,E)-4-(2-oxo-4-phenyloxazolidin-3-yl)but-3-enoate
  参考文献：
  名称：

  Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover

  摘要：

  A carbon-carbon bond construction method is disclosed which involves radical addition of alpha-haloesters or iodoacetonitrile to enamides. Despite the presence of tri-n-butylstannane, nonreductive addition was predominant; H-atom transfer from tin hydride was not observed. Rapid iodine atom transfer to (or electron transfer from) the radical adduct, resulting in an iminium ion intermediate and radical chain propagation, is consistent with the observed reactivity.

  DOI：

  10.1021/ol8028077

文献信息

• Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with <i>N</i>-Chloro-<i>N</i>-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts
  作者：Yuta Murakami、Youhei Takeda、Satoshi Minakata

  DOI：10.1021/jo2010632

  日期：2011.8.5

  Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,S,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.
• Intermolecular Nonreductive Alkylation of Enamides via Radical−Polar Crossover
  作者：Gregory K. Friestad、Yaoping Wu

  DOI：10.1021/ol8028077

  日期：2009.2.19

  A carbon-carbon bond construction method is disclosed which involves radical addition of alpha-haloesters or iodoacetonitrile to enamides. Despite the presence of tri-n-butylstannane, nonreductive addition was predominant; H-atom transfer from tin hydride was not observed. Rapid iodine atom transfer to (or electron transfer from) the radical adduct, resulting in an iminium ion intermediate and radical chain propagation, is consistent with the observed reactivity.