(3S,4S)-6-(4-methoxyphenyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one | 1453495-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3S,4S)-6-(4-methoxyphenyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one
• 英文别名: (3S,4S)-6-(4-methoxyphenyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydropyran-2-one
• CAS: 1453495-92-5
• 化学式: C₁₄H₁₃F₃O₃
• 分子量: 286.251
• InChiKey: ZAVKQEPEWQPELE-KWQFWETISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,4,4-trifluoro-1-(4-methoxyphenyl)but-2-yn-1-ol 在 (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 56.0h， 生成 (3S,4S)-6-(4-methoxyphenyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 、 6-(4-methoxyphenyl)-3-methyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Stereospecific Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights

  摘要：

  N-Heterocyclic carbene (NHC)-catalyzed redox asymmetric hetero-Diels-Alder reactions of alpha-aroyloxyaldehydes with beta-trifluoromethyl enones generates synthetically useful dihydropyranones containing a stereogenic trifluoromethyl substituent in good yields (up to 81%) and excellent diastereoselectivity and enantioselectivity (up to >95:5 dr and >99% ee). The process is stereospecific, with use of either (E)- or (Z)-beta-trifluoromethyl enones forming syn- or anti-dihydropyranone products, respectively. Mechanistic studies through in situ kinetic analysis of the reaction reveal key differences in reactivity between chiral NHC precursor 1 and an achiral NHC precursor.

  DOI：

  10.1021/jo401433q

文献信息

• Stereospecific Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights
  作者：Alyn T. Davies、James E. Taylor、James Douglas、Christopher J. Collett、Louis C. Morrill、Charlene Fallan、Alexandra M. Z. Slawin、Gwydion Churchill、Andrew D. Smith

  DOI：10.1021/jo401433q

  日期：2013.9.20

  N-Heterocyclic carbene (NHC)-catalyzed redox asymmetric hetero-Diels-Alder reactions of alpha-aroyloxyaldehydes with beta-trifluoromethyl enones generates synthetically useful dihydropyranones containing a stereogenic trifluoromethyl substituent in good yields (up to 81%) and excellent diastereoselectivity and enantioselectivity (up to >95:5 dr and >99% ee). The process is stereospecific, with use of either (E)- or (Z)-beta-trifluoromethyl enones forming syn- or anti-dihydropyranone products, respectively. Mechanistic studies through in situ kinetic analysis of the reaction reveal key differences in reactivity between chiral NHC precursor 1 and an achiral NHC precursor.