N-{2-[3-bromo-5-(5-[13C]cyano-4-cyclopropyl-2-ethyl-imidazol-1-ylmethyl)-benzofuran-2-yl]-phenyl}-C,C,C-trifluoromethanesulphonamide | 146624-31-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: N-{2-[3-bromo-5-(5-[13C]cyano-4-cyclopropyl-2-ethyl-imidazol-1-ylmethyl)-benzofuran-2-yl]-phenyl}-C,C,C-trifluoromethanesulphonamide
• 英文别名: N-[2-[5-[[5-(azanylidyne(113C)methyl)-4-cyclopropyl-2-ethylimidazol-1-yl]methyl]-3-bromo-1-benzofuran-2-yl]phenyl]-1,1,1-trifluoromethanesulfonamide
• CAS: 146624-31-9
• 化学式: C₂₅H₂₀BrF₃N₄O₃S
• 分子量: 594.413
• InChiKey: ROQZMBSBFYUIKB-HNHCFKFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-{2-[3-bromo-5-(5-[13C]cyano-4-cyclopropyl-2-ethyl-imidazol-1-ylmethyl)-benzofuran-2-yl]-phenyl}-C,C,C-trifluoromethanesulphonamide 在 ammonium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 1.33h， 以64.2%的产率得到3-{3-bromo-2-[2-(trifluoromethanesulphonylamino)-phenyl]-benzofuran-5-ylmethyl}-cyclopropyl-2-ethyl-3H-imidazole-4-[13C]-carboxylic amide
  参考文献：
  名称：

  Syntheses of isotopically labelled angiotensin II receptor antagonist GR138950X

  摘要：

  Syntheses of [C-13] and [C-14]-labelled versions of angiotensin II receptor antagonist GR138950X, labelled in the imidazole carboxamide residue, are described. These involved preparation of an iodoimidazole substrate by a novel iododecarboxylation procedure, followed by cyanation with a mixture of carbon-labelled potassium cyanide and copper (I) iodide in DMF at high temperature. The preparation of a mass-labelled (M+5) version of GR138950X is also described. This involved the synthesis of an [C-13(3), N-15(2)]-labelled imidazole from a 1,2,3-tricarbonyl compound, C-13(3)]propionaldehyde and [N-15]ammonia. The labelled imidazole was further elaborated into multiply-labelled GR138950X.

  DOI：

  10.1002/(sici)1099-1344(199605)38:5<453::aid-jlcr852>3.0.co;2-#
• 作为产物：
  描述：

  3-<3-bromo-2-(2-nitrophenyl)-benzofuran-5-ylmethyl>-5-cyclopropyl-2-ethyl-3H-imidazole-<4-13C>-carbonitrile 在 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 6.33h， 生成 N-{2-[3-bromo-5-(5-[13C]cyano-4-cyclopropyl-2-ethyl-imidazol-1-ylmethyl)-benzofuran-2-yl]-phenyl}-C,C,C-trifluoromethanesulphonamide
  参考文献：
  名称：

  Syntheses of isotopically labelled angiotensin II receptor antagonist GR138950X

  摘要：

  Syntheses of [C-13] and [C-14]-labelled versions of angiotensin II receptor antagonist GR138950X, labelled in the imidazole carboxamide residue, are described. These involved preparation of an iodoimidazole substrate by a novel iododecarboxylation procedure, followed by cyanation with a mixture of carbon-labelled potassium cyanide and copper (I) iodide in DMF at high temperature. The preparation of a mass-labelled (M+5) version of GR138950X is also described. This involved the synthesis of an [C-13(3), N-15(2)]-labelled imidazole from a 1,2,3-tricarbonyl compound, C-13(3)]propionaldehyde and [N-15]ammonia. The labelled imidazole was further elaborated into multiply-labelled GR138950X.

  DOI：

  10.1002/(sici)1099-1344(199605)38:5<453::aid-jlcr852>3.0.co;2-#