2-methyl-3-(2-thienyl)-4,5,5-trifluoro-4-trifluoromethyl-isoxazolidine | 1040354-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-methyl-3-(2-thienyl)-4,5,5-trifluoro-4-trifluoromethyl-isoxazolidine
• 英文别名: 4,5,5-Trifluoro-2-methyl-3-thiophen-2-yl-4-(trifluoromethyl)-1,2-oxazolidine
• CAS: 1040354-91-3
• 化学式: C₉H₇F₆NOS
• 分子量: 291.217
• InChiKey: KRGDDFACKPROHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(2-thienyl)-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， 生成 1-methyl-3-fluoro-3-trifluoromethyl-4-(2-thienyl)-2-azetidinone 、 1-methyl-3-fluoro-3-trifluoromethyl-4-(2-thienyl)-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：

  六氟丙烯 、 N-methyl-thienyl-2-methyleneamine N-oxide 以 乙腈 为溶剂， 反应 24.0h， 以63%的产率得到2-methyl-3-(2-thienyl)-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