(R)-5H-5-methyl-5-[(Z)-3-oxo-3-(pyrrolidin-1-yl)propenyl]-2-phenyloxazol-4-one | 1286783-61-6

• 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-methyl-5-[(Z)-3-oxo-3-(pyrrolidin-1-yl)propenyl]-2-phenyloxazol-4-one
• CAS: 1286783-61-6
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: YVFUMSBIWPBLRC-DOOKAGJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.97
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-5H-5-methyl-5-[(Z)-3-oxo-3-(pyrrolidin-1-yl)propenyl]-2-phenyloxazol-4-one 在 palladium 10% on activated carbon 、 lithium methanolate 、 氢气 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 100.0h， 生成 (5R)-γ-valerolactone γ-carboxylic acid
  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
• 作为产物：
  描述：

  (9CI)-1-(1-氧代-2-丙炔)-吡咯烷 、 5-methyl-2-phenyloxazol-4(5H)-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 22.0h， 以50%的产率得到(R)-5H-5-methyl-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