3-<3-bromo-2-(2-nitrophenyl)-benzofuran-5-ylmethyl>-5-cyclopropyl-2-ethyl-3H-imidazole-<4-13C>-carbonitrile | 146624-95-5

• 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: 3-<3-bromo-2-(2-nitrophenyl)-benzofuran-5-ylmethyl>-5-cyclopropyl-2-ethyl-3H-imidazole-<4-13C>-carbonitrile
• 英文别名: 3-[[3-Bromo-2-(2-nitrophenyl)-1-benzofuran-5-yl]methyl]-5-cyclopropyl-2-ethylimidazole-4-carbonitrile
• CAS: 146624-95-5
• 化学式: C₂₄H₁₉BrN₄O₃
• 分子量: 492.333
• InChiKey: RUHVGLOAIVFLIX-HNHCFKFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以81.1%的产率得到3-[2-(2-aminophenyl)-3-bromobenzofuran-5-ylmethyl]-5-cyclopropyl-2-ethyl-3H-imidazole-[4-13C]-carbonitrile
  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：

  1-<3-bromo-2-(2-nitrophenyl)-benzofuran-5-ylmethyl>-4-cyclopropyl-2-ethyl-5-iodo-1H-imidazole 以86%的产率得到
  参考文献：
  名称：

  Carr Richard M., Cable Karl M., Wells Guy N., Suthertand Derek R., J. Labell. Compounds and Radiopharm, 34 (1994) N 9, S 887-897

  摘要：

  DOI：

文献信息

• A convenient method for cyanation of aromatic iodo compounds
  作者：Richard M Carr、Karl M Cable、Guy N Wells、Derek R Sutherland

  DOI：10.1002/jlcr.2580340910

  日期：1994.9

  A variety of [13C]-labelled aromatic nitriles have been prepared in good yield from iodoaromatic substrates. Cyanation was achieved by reaction of aryl iodides with a mixture of potassium [13C]-cyanide and copper (I) iodide in an aprotic solvent at high temperature. The use of pre-prepared carbon-labelled copper (I) cyanide was therefore obviated.

  各种[13C]-标记的芳香腈已经从碘芳香底物以良好的产率制备。氰化是通过芳基碘化物与 [13C]-氰化钾和碘化铜 (I) 的混合物在非质子溶剂中在高温下反应来实现的。因此避免使用预先制备的碳标记的氰化铜 (I)。