5H-5-methyl-2-(4-trifluoromethylphenyl)oxazol-4-one | 1286783-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5H-5-methyl-2-(4-trifluoromethylphenyl)oxazol-4-one
• 英文别名: 5-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-one；5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-one
• CAS: 1286783-47-8
• 化学式: C₁₁H₈F₃NO₂
• 分子量: 243.185
• InChiKey: NVWQVIIKPMTKHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5H-5-methyl-2-(4-trifluoromethylphenyl)oxazol-4-one 、 丙炔酸甲酯 在 (S)-bis[3,5-bis(trifluoromethyl)phenyl](3,3-dimethyl-1,5,7-triazabicyclo-[4.3.0]-non-5-ene-8-yl)methanol 作用下， 以 甲苯 为溶剂， 反应 38.0h， 生成 methyl (Z)-3-[(S)-5H-5-methyl-4-oxo-2-(4-trifluoromethylphenyl)oxazol-5-yl]propenoate 、 methyl (Z)-3-[(R)-5H-5-methyl-4-oxo-2-(4-trifluoromethylphenyl)oxazol-5-yl]propenoate
  参考文献：
  名称：

  HighlyZ-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines

  摘要：

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.

  DOI：

  10.1021/ja200283n

文献信息

• Highly<i>Z</i>-Selective Asymmetric 1,4-Addition Reaction of 5<i>H</i>-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines
  作者：Tomonori Misaki、Kei Kawano、Takashi Sugimura

  DOI：10.1021/ja200283n

  日期：2011.4.20

  An asymmetric I,4-addition reaction of 5H-oxazol-4-ones with alkynyl carbonyl compounds was developed, and, for the first time, high enantiomeric and geometric control was achieved to afford the thermodynamically unstable Z-isomer predominantly using chiral guanidine catalysts bearing a hydroxy group at the appropriate position. The method provides synthetically useful gamma-butenolide ester bearing a chiral quaternary stereogenic center.