3-[4-(4-fluorophenyl)-5-(5-methyl(2-furyl))imidazolyl]propanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[4-(4-fluorophenyl)-5-(5-methyl(2-furyl))imidazolyl]propanoic acid
• 英文别名: 3-[4-(4-Fluorophenyl)-5-(5-methylfuran-2-yl)imidazol-1-yl]propanoic acid
• 化学式: C₁₇H₁₅FN₂O₃
• 分子量: 314.316
• InChiKey: YVXNYDUEJGYODJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-甲基呋喃醛 、 Α-(对甲苯磺酰基)-4-氟苄基异腈 、 β-丙氨酸 在 sodium hydroxide 、 哌嗪 作用下， 以 甲醇 、 水 为溶剂， 反应 19.5h， 以76%的产率得到3-[4-(4-fluorophenyl)-5-(5-methyl(2-furyl))imidazolyl]propanoic acid
  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

文献信息

• An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents¹
  作者：Joseph Sisko、Andrew J. Kassick、Mark Mellinger、John J. Filan、Andrew Allen、Mark A. Olsen

  DOI：10.1021/jo991782l

  日期：2000.3.1

  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.