2-methyl-3-(3-pyridyl)-4,5,5-trifluoro-4-trifluoromethyl-isoxazolidine | 1040354-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: 2-methyl-3-(3-pyridyl)-4,5,5-trifluoro-4-trifluoromethyl-isoxazolidine
• CAS: 1040354-93-5
• 化学式: C₁₀H₈F₆N₂O
• 分子量: 286.177
• InChiKey: IODHOFZGLHMXHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.36
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(3-pyridyl)-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 20.0h， 生成 1-methyl-3-fluoro-3-trifluoromethyl-4-(3-pyridyl)-2-azetidinone 、 1-methyl-3-fluoro-3-trifluoromethyl-4-(3-pyridyl)-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
• 作为产物：
  描述：

  N-甲基-N-[(Z)-3-吡啶基甲基烯]胺氧化物 、 六氟丙烯 以 乙腈 为溶剂， 反应 168.0h， 以73%的产率得到2-methyl-3-(3-pyridyl)-4,5,5-trifluoro-4-trifluoromethyl-isoxazolidine
  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