methyl (Z)-3-[(R)-5H-5-methyl-4-oxo-2-phenyloxazol-5-yl]propenoate | 1286783-51-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-3-[(R)-5H-5-methyl-4-oxo-2-phenyloxazol-5-yl]propenoate
• 英文别名: methyl (Z)-3-[(5R)-5-methyl-4-oxo-2-phenyl-1,3-oxazol-5-yl]prop-2-enoate
• CAS: 1286783-51-4
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: IDLJXGQKDQVJPA-QIAWRQBBSA-N

物化性质

• 熔点：
  70-73 °C
• 沸点：
  353.4±52.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-[(R)-5H-5-methyl-4-oxo-2-phenyloxazol-5-yl]propenoate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.4h， 生成
  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：

  丙炔酸甲酯 、 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 11.0h， 以56%的产率得到methyl (Z)-3-[(R)-5H-5-methyl-4-oxo-2-phenyloxazol-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