(2S,4R)-2-difluoromethyl-2,4-diphenyl-1,3-oxazolidine | 1018434-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,4R)-2-difluoromethyl-2,4-diphenyl-1,3-oxazolidine
• CAS: 1018434-44-0
• 化学式: C₁₆H₁₅F₂NO
• 分子量: 275.298
• InChiKey: MISCWDMCXIYDQC-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-difluoromethyl-2,4-diphenyl-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-((1R)-1-phenyl-2-hydroxyethyl)-2,2-difluoro-1-phenylethylamine
  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：

  D-苯甘氨醇 、 2,2-difluoro-1-phenyl-1-trimethylsiloxyethene 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以50%的产率得到(2S,4R)-2-difluoromethyl-2,4-diphenyl-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