(Z)-3-(5-fluoro-1-trityl-1H-imidazol-4-yl)-acrylic acid methyl ester | 464924-67-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (Z)-3-(5-fluoro-1-trityl-1H-imidazol-4-yl)-acrylic acid methyl ester
• CAS: 464924-67-2
• 化学式: C₂₆H₂₁FN₂O₂
• 分子量: 412.463
• InChiKey: KIEGRBWTKOQBKX-ZCXUNETKSA-N

物化性质

• 沸点：
  548.2±45.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-(5-fluoro-1-trityl-1H-imidazol-4-yl)-acrylic acid methyl ester 在 sodium hydroxide 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 50.5h， 生成 (Z)-3-(4-fluoro-1H-imidazol-5-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
• 作为产物：
  描述：

  O,O'-双(2,2,2-三氟乙基)磷乙酸甲酯 、 1-trityl-5-fluoroimidazole-4-carboxaldehyde 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.17h， 以72%的产率得到(Z)-3-(5-fluoro-1-trityl-1H-imidazol-4-yl)-acrylic acid methyl ester
  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