1-[4-(4-fluorophenyl)-1,3-oxazol-5-yl]ethan-1-one | 263389-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[4-(4-fluorophenyl)-1,3-oxazol-5-yl]ethan-1-one
• 英文别名: 1-[4-(4-Fluorophenyl)-5-oxazolyl]ethanone；1-[4-(4-fluorophenyl)-1,3-oxazol-5-yl]ethanone
• CAS: 263389-47-5
• 化学式: C₁₁H₈FNO₂
• 分子量: 205.188
• InChiKey: WLQMNDNVGHKYNY-UHFFFAOYSA-N

物化性质

• 熔点：
  59-61 °C
• 沸点：
  340.4±32.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Α-(对甲苯磺酰基)-4-氟苄基异腈 、 丙酮醛 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以71%的产率得到1-[4-(4-fluorophenyl)-1,3-oxazol-5-yl]ethan-1-one
  参考文献：
  名称：

  An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents¹

  摘要：

  This article describes efficient and mild protocols for preparing polysubstituted imidazoles in a single pot fi om aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ. Traditional imine-forming reactions employing virtually any aldehyde and amine followed by addition of the TosMIC reagent delivers 1,4,5-trisubstituted imidazoles with predictable regiochemistry. Employing chiral amines and aldehydes, particularly those derived from or-amino acids, affords imidazoles with asymmetric centers appended to N-1 or C-5 with excellent retention of chiral purity. 1,4-Disubstituted imidazoles are also readily prepared by a simple variant of the above procedure. Selecting glyoxylic acid as the aldehyde component of this procedure leads to intermediates such as 48, which readily undergo decarboxylation and elimination oft;he tosyl moiety to deliver 1,4-disubstituted imidazoles in high yields. Alternatively, using NH4OH as the amine component in conjunction with a variety of aldehydes delivers 4,5-disubstituted imidazoles in moderate to good yields in a single pot while avoiding the need for protecting groups. Finally, the facile preparation of mono- and disubstituted oxazoles from these TosMIC reagents and aldehydes is described.

  DOI：

  10.1021/jo991782l