(2S,4R)-N-benzoyl-2-difluoromethyl-2-methyl-4-phenyl-1,3-oxazolidine | 1018434-51-9

• 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: (2S,4R)-N-benzoyl-2-difluoromethyl-2-methyl-4-phenyl-1,3-oxazolidine
• 英文别名: [(2S,4R)-2-(difluoromethyl)-2-methyl-4-phenyl-1,3-oxazolidin-3-yl]-phenylmethanone
• CAS: 1018434-51-9
• 化学式: C₁₈H₁₇F₂NO₂
• 分子量: 317.335
• InChiKey: IJNGFQAKMAKICS-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-N-benzoyl-2-difluoromethyl-2-methyl-4-phenyl-1,3-oxazolidine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以83%的产率得到(1R)-N-benzyl-N-((1R)-1-phenyl-2-hydroxyethyl)-2,2-difluoro-1-methylethylamine
  参考文献：
  名称：

  Umpolung Reactivity of Difluoroenol Silyl Ethers with Amines and Amino Alcohols. Application to the Synthesis of Enantiopure α-Difluoromethyl Amines and Amino Acids

  摘要：

  Difluoroenol silyl ethers, produced in situ from acylsilanes and CF3TMS, react as electrophiles with amines to give difluoroimines, via the corresponding hemiaminal adduct, as evidenced by F-19 NMR spectroscopy. Reaction with (R)-phenylglycinol led to 2-difluoromethyloxazolidines. After separation of the diastereomers, reduction with LAH and Strecker-type synthesis gave enantiopure alpha-difluoromethy-lamines and alpha-difluoromethyl-alpha-amino acids, respectively.

  DOI：

  10.1021/jo702328v
• 作为产物：
  描述：

  (E)-2,2-difluoro-1-methylethylidene((1R)-2-trimethylsilyloxy-1-phenylethyl)amine 、 苯甲酰氯 在 四丁基氟化铵 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 二氯甲烷 为溶剂， 以0.67 g的产率得到(2S,4R)-N-benzoyl-2-difluoromethyl-2-methyl-4-phenyl-1,3-oxazolidine
  参考文献：
  名称：

  Umpolung Reactivity of Difluoroenol Silyl Ethers with Amines and Amino Alcohols. Application to the Synthesis of Enantiopure α-Difluoromethyl Amines and Amino Acids

  摘要：

  Difluoroenol silyl ethers, produced in situ from acylsilanes and CF3TMS, react as electrophiles with amines to give difluoroimines, via the corresponding hemiaminal adduct, as evidenced by F-19 NMR spectroscopy. Reaction with (R)-phenylglycinol led to 2-difluoromethyloxazolidines. After separation of the diastereomers, reduction with LAH and Strecker-type synthesis gave enantiopure alpha-difluoromethy-lamines and alpha-difluoromethyl-alpha-amino acids, respectively.

  DOI：

  10.1021/jo702328v

文献信息

• Umpolung Reactivity of Difluoroenol Silyl Ethers with Amines and Amino Alcohols. Application to the Synthesis of Enantiopure α-Difluoromethyl Amines and Amino Acids
  作者：Florent Huguenot、Anne Billac、Thierry Brigaud、Charles Portella

  DOI：10.1021/jo702328v

  日期：2008.4.1

  Difluoroenol silyl ethers, produced in situ from acylsilanes and CF3TMS, react as electrophiles with amines to give difluoroimines, via the corresponding hemiaminal adduct, as evidenced by F-19 NMR spectroscopy. Reaction with (R)-phenylglycinol led to 2-difluoromethyloxazolidines. After separation of the diastereomers, reduction with LAH and Strecker-type synthesis gave enantiopure alpha-difluoromethy-lamines and alpha-difluoromethyl-alpha-amino acids, respectively.