(E)-ethyl 2-fluoro-3-(1-trityl-1H-imidazol-4-yl)-prop-2-enoate | 151629-26-4

• 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: (E)-ethyl 2-fluoro-3-(1-trityl-1H-imidazol-4-yl)-prop-2-enoate
• 英文别名: Ethyl 1'-trityl-(E)-4'-imidazole-2-fluoro-3-acrylate；ethyl (E)-2-fluoro-3-(1-tritylimidazol-4-yl)prop-2-enoate
• CAS: 151629-26-4
• 化学式: C₂₇H₂₃FN₂O₂
• 分子量: 426.49
• InChiKey: FEEHAVRTHGHDAU-XIEYBQDHSA-N

物化性质

• 沸点：
  561.5±50.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-fluoro-3-(1-trityl-1H-imidazol-4-yl)-prop-2-enoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到(E)-2-fluoro-3-(1-trityl-1H-imidazol-4-yl)-prop-2-en-1-ol
  参考文献：
  名称：

  Methods for the stereoselective synthesis of 2-fluoroalkenoates. Carbonyl condensation reactions of 3,3-bis(methylthio)-2-fluoropropenal, a highly-functionalized fluoroacrylate cation equivalent

  摘要：

  New methodology for the preparation of 2-fluoroacrylates has been developed on the basis of the reagent 3,3-bis(methylthio)-2-fluoropropenal. This highly-functionalized aldehyde is prepared by the condensation of carbon disulfide with fluoroacetonitrile followed by reduction of the nitrile. It is subjected to nucleophilic addition with organometallic reagents and enolates to yield allylic alcohol products that can be rearranged under acidic conditions to (Z)-2-fluoroacrylate thioesters. Other desired fluoroacrylates are also available via conventional fluorinated Homer-Wadsworth-Emmons or Reformatsky reagents.

  DOI：

  10.1021/jo00073a029
• 作为产物：
  描述：

  2-氟-2-磷酰基乙酸三乙酯 、 1-三苯甲基咪唑-4-甲醛 在 正丁基锂 作用下， 以 乙二醇二甲醚 、 正己烷 为溶剂， 以65%的产率得到(E)-ethyl 2-fluoro-3-(1-trityl-1H-imidazol-4-yl)-prop-2-enoate
  参考文献：
  名称：

  Methods for the stereoselective synthesis of 2-fluoroalkenoates. Carbonyl condensation reactions of 3,3-bis(methylthio)-2-fluoropropenal, a highly-functionalized fluoroacrylate cation equivalent

  摘要：

  New methodology for the preparation of 2-fluoroacrylates has been developed on the basis of the reagent 3,3-bis(methylthio)-2-fluoropropenal. This highly-functionalized aldehyde is prepared by the condensation of carbon disulfide with fluoroacetonitrile followed by reduction of the nitrile. It is subjected to nucleophilic addition with organometallic reagents and enolates to yield allylic alcohol products that can be rearranged under acidic conditions to (Z)-2-fluoroacrylate thioesters. Other desired fluoroacrylates are also available via conventional fluorinated Homer-Wadsworth-Emmons or Reformatsky reagents.

  DOI：

  10.1021/jo00073a029

文献信息

• Methods for the stereoselective synthesis of 2-fluoroalkenoates. Carbonyl condensation reactions of 3,3-bis(methylthio)-2-fluoropropenal, a highly-functionalized fluoroacrylate cation equivalent
  作者：Michael C. Pirrung、Elizabeth G. Rowley、Christopher P. Holmes

  DOI：10.1021/jo00073a029

  日期：1993.10

  New methodology for the preparation of 2-fluoroacrylates has been developed on the basis of the reagent 3,3-bis(methylthio)-2-fluoropropenal. This highly-functionalized aldehyde is prepared by the condensation of carbon disulfide with fluoroacetonitrile followed by reduction of the nitrile. It is subjected to nucleophilic addition with organometallic reagents and enolates to yield allylic alcohol products that can be rearranged under acidic conditions to (Z)-2-fluoroacrylate thioesters. Other desired fluoroacrylates are also available via conventional fluorinated Homer-Wadsworth-Emmons or Reformatsky reagents.