(R)-5H-5-(1-methylethyl)-5-[(Z)-3-oxo-3-(pyrrolidin-1-yl)propenyl]-2-phenyloxazol-4-one | 1286783-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-5H-5-(1-methylethyl)-5-[(Z)-3-oxo-3-(pyrrolidin-1-yl)propenyl]-2-phenyloxazol-4-one
• 英文别名: (5R)-5-[(Z)-3-oxo-3-pyrrolidin-1-ylprop-1-enyl]-2-phenyl-5-propan-2-yl-1,3-oxazol-4-one
• CAS: 1286783-63-8
• 化学式: C₁₉H₂₂N₂O₃
• 分子量: 326.395
• InChiKey: OUKOROBAIAOSNG-GDWUOILNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (9CI)-1-(1-氧代-2-丙炔)-吡咯烷 、 5H-5-(methyl)ethyl-2-phenyl-2-oxazol-4-one 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 71.0h， 以55%的产率得到(R)-5H-5-(1-methylethyl)-5-[(Z)-3-oxo-3-(pyrrolidin-1-yl)propenyl]-2-phenyloxazol-4-one
  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.