1-methyl-3-fluoro-3-trifluoromethyl-4,4-diphenyl-2-azetidinone | 1040355-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-methyl-3-fluoro-3-trifluoromethyl-4,4-diphenyl-2-azetidinone
• CAS: 1040355-37-0
• 化学式: C₁₇H₁₃F₄NO
• 分子量: 323.29
• InChiKey: CMUQNHXPOQUEHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-methyl-3,3-diphenyl-4,5,5-trifluoro-4-trifluoromethyl-isoxazolidine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以95%的产率得到1-methyl-3-fluoro-3-trifluoromethyl-4,4-diphenyl-2-azetidinone
  参考文献：
  名称：

  Synthesis of α-Trifluoromethyl-β-lactams and Esters of β-Amino Acids via 1,3-Dipolar Cycloaddition of Nitrones to Fluoroalkenes

  摘要：

  Nitrones derived from aromatic or aliphatic aldehydes or ketones react with hexafluoropropene (HFP) or 2H-pentafluoropropene (PFP) to give the respective fluorinated isoxazolidine derivatives in good yields with complete regioselectivity and moderate diastereoselectivity. Catalytic hydrogenolysis of the N-O bond under ambient pressure and temperature leads to fluorides of beta-amino acids that undergo cyclization to alpha-trifluoromethylated beta-lactams or, under acidic conditions, form esters of alpha-trifluoromethylated beta-amino acids.

  DOI：

  10.1021/jo800721w

文献信息

• Synthesis of α-Trifluoromethyl-β-lactams and Esters of β-Amino Acids via 1,3-Dipolar Cycloaddition of Nitrones to Fluoroalkenes
  作者：Jakub Jakowiecki、Rafał Loska、Mieczysław Makosza

  DOI：10.1021/jo800721w

  日期：2008.7.1

  Nitrones derived from aromatic or aliphatic aldehydes or ketones react with hexafluoropropene (HFP) or 2H-pentafluoropropene (PFP) to give the respective fluorinated isoxazolidine derivatives in good yields with complete regioselectivity and moderate diastereoselectivity. Catalytic hydrogenolysis of the N-O bond under ambient pressure and temperature leads to fluorides of beta-amino acids that undergo cyclization to alpha-trifluoromethylated beta-lactams or, under acidic conditions, form esters of alpha-trifluoromethylated beta-amino acids.