methyl 2-(3-cyanophenyl)-1,3-oxazole-4-carboxylate | 1239589-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(3-cyanophenyl)-1,3-oxazole-4-carboxylate
• 英文别名: Methyl 2-(3-cyanophenyl)-1,3-oxazole-4-carboxylate
• CAS: 1239589-18-4
• 化学式: C₁₂H₈N₂O₃
• mdl: MFCD24842961
• 分子量: 228.207
• InChiKey: KJKNBDLOJVEXGD-UHFFFAOYSA-N

物化性质

• 沸点：
  392.4±48.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氰基苯甲醛 、 L-丝氨酸甲酯盐酸盐 在 potassium carbonate 、 三氯溴甲烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以80%的产率得到methyl 2-(3-cyanophenyl)-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  A Direct Synthesis of Oxazoles from Aldehydes

  摘要：

  An expedient method for the direct conversion of aldehydes to 2,4-disubstituted oxazoles is presented. The method relies on the oxidation of an oxazolidine formed from the condensation of serine with an aldehyde and proceeds through a 2,5-dihydrooxazole intermediate. In contrast to standard methods that start from carboxylic acids, the use of aldehydes as starting materials does not require intermediate purification and affords the oxazoles under relatively mild conditions.

  DOI：

  10.1021/ol101346w

文献信息

• A Direct Synthesis of Oxazoles from Aldehydes
  作者：Thomas H. Graham

  DOI：10.1021/ol101346w

  日期：2010.8.20

  An expedient method for the direct conversion of aldehydes to 2,4-disubstituted oxazoles is presented. The method relies on the oxidation of an oxazolidine formed from the condensation of serine with an aldehyde and proceeds through a 2,5-dihydrooxazole intermediate. In contrast to standard methods that start from carboxylic acids, the use of aldehydes as starting materials does not require intermediate purification and affords the oxazoles under relatively mild conditions.