(E)-3-(2-fluoro-1H-imidazol-4-yl)-acrylic acid | 60010-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-3-(2-fluoro-1H-imidazol-4-yl)-acrylic acid
• 英文别名: (E)-2-fluorourocanic acid；Imidazole, 2-fluoro-5-[2-carboxyvinyl]-；(E)-3-(2-fluoro-1H-imidazol-5-yl)prop-2-enoic acid
• CAS: 60010-46-0
• 化学式: C₆H₅FN₂O₂
• 分子量: 156.116
• InChiKey: CEXJVOYUMZSGHY-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-3-(2-fluoro-1-trityl-1H-imidazol-4-yl)-acrylic acid ethyl ester 在 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 51.5h， 生成 (E)-3-(2-fluoro-1H-imidazol-4-yl)-acrylic acid
  参考文献：
  名称：

  Syntheses of E- and Z-2- and 4-fluorourocanic acids

  摘要：

  Homer-Wadsworth-Emmons olefination of ring-fluorinated N-trityl-imidazole carboxaldehydes with dialkyphosphonoacetic acid esters produced ring-fluorinated imidazolyl-E- and Z-acrylate esters. Stereochemistry was controlled by choice of phoshonate. Acid catalyzed removal of trityl followed by ester saponification gave the target 2- and 4-fluoro-E- and Z-urocanic acid derivatives. These are being investigated as potential mediators of photo-immunosupression. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00045-3

文献信息

• Syntheses of E- and Z-2- and 4-fluorourocanic acids
  作者：Junfa Fan、Bohumil Dolensky、In Ho Kim、Kenneth L Kirk

  DOI：10.1016/s0022-1139(02)00045-3

  日期：2002.6

  Homer-Wadsworth-Emmons olefination of ring-fluorinated N-trityl-imidazole carboxaldehydes with dialkyphosphonoacetic acid esters produced ring-fluorinated imidazolyl-E- and Z-acrylate esters. Stereochemistry was controlled by choice of phoshonate. Acid catalyzed removal of trityl followed by ester saponification gave the target 2- and 4-fluoro-E- and Z-urocanic acid derivatives. These are being investigated as potential mediators of photo-immunosupression. (C) 2002 Elsevier Science B.V. All rights reserved.