1-[1-(2,2-dimethoxyethyl)-4-(4-fluorophenyl)imidazol-5-yl]ethan-1-one

• 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-[1-(2,2-dimethoxyethyl)-4-(4-fluorophenyl)imidazol-5-yl]ethan-1-one
• 英文别名: 1-[3-(2,2-Dimethoxyethyl)-5-(4-fluorophenyl)imidazol-4-yl]ethanone
• 化学式: C₁₅H₁₇FN₂O₃
• 分子量: 292.31
• InChiKey: VHKJIFRSOOYAFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  氨基乙醛缩二甲醇 、 Α-(对甲苯磺酰基)-4-氟苄基异腈 、 丙酮醛 在 哌嗪 、 盐酸 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 18.42h， 以71%的产率得到1-[1-(2,2-dimethoxyethyl)-4-(4-fluorophenyl)imidazol-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