(S)-5-((S)-1-(4-isopropylphenyl)-2-nitroethyl)-5-methyl-2-(m-tolyl)oxazol-4(5H)-one | 1432619-02-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-5-((S)-1-(4-isopropylphenyl)-2-nitroethyl)-5-methyl-2-(m-tolyl)oxazol-4(5H)-one
• CAS: 1432619-02-7
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: NLICCFFHEFGGMQ-KNQAVFIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.8
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-isopropyl-4-(2-nitrovinyl)benzene 、 5-methyl-2-(m-tolyl)oxazol-4(5H)-one 在 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(3,3-dimethyl-1-(piperidin-1-yl)butan-2-yl)thiourea 作用下， 以 甲基叔丁基醚 为溶剂， 反应 40.5h， 以99%的产率得到(S)-5-((S)-1-(4-isopropylphenyl)-2-nitroethyl)-5-methyl-2-(m-tolyl)oxazol-4(5H)-one
  参考文献：
  名称：

  Organocatalytic Asymmetric Michael Addition of 5H-Oxazol-4-ones to Nitroolefins

  摘要：

  The first organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral alpha-alkyl-alpha-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds.

  DOI：

  10.1021/ol401062z