(Z)-1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde oxime | 134420-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde oxime
• 英文别名: (NZ)-N-[[4-iodo-1-(phenylmethoxymethyl)imidazol-2-yl]methylidene]hydroxylamine
• CAS: 134420-52-3
• 化学式: C₁₂H₁₂IN₃O₂
• 分子量: 357.151
• InChiKey: LIJYWEMVGLFRFB-NSIKDUERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde 在 羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到(Z)-1-<(benzyloxy)methyl>-4-iodoimidazole-2-carboxaldehyde oxime
  参考文献：
  名称：

  Regioselective formation of imidazol-2-yllithium, imidazol-4-yllithium, and imidazol-5-yllithium species

  摘要：

  Representative imidazol-2-yllithium, imidazol-4-yllithium, and imidazol-5-yllithium species have been prepared via halogen-metal exchange, and the propensity of the latter two to undergo isomerization and quench by electrophilic reagents has been studied. The C2-unsubstituted imidazol-5-yllithium species 3 is generated within 10 min at -78-degrees-C from 1-[(benzyloxy)methyl]-4,5-diiodoimidazole (1b) and affords the C5-formyl product 4 upon reaction with DMF, but gives the isomeric C2-formyl product 6 if allowed to equilibrate to the imidazol-2-yllithium species 5 for an additional 35 min at -78-degrees-C before quench. The less reactive electrophile diethyl carbonate is unable to trap 3 and instead reacts with 5 to afford tris[1-[(benzyloxy)methyl]-4-iodo-2-imidazolyl]carbinol (7). In contrast, 1-[(benzyloxy)methyl]-4-iodoimidazole-5-carboxaldehyde ethylene acetal (10) metalates to give the C2-unsubstituted imidazol-4-yllithium species 13, which undergoes a very rapid conversion to its imidazol-2-yllithium isomer 14, even at -100-degrees-C, giving the 2,5-dicarboxaldehyde 5-ethylene acetal 16 or the 2-deuterio-5-carboxaldehyde ethylene acetal 15 upon quench with DMF or D2O, respectively. Thus, in the presence of C2 unsubstitution, C5 functionalization could be accomplished when the electrophile was sufficiently reactive, while C4 functionalization could not. Short- and long-range H-1-C-13 heteronuclear (Hector) 2D NMR spectroscopic analyses were instrumental in the structural assignments of key compounds.

  DOI：

  10.1021/jo00013a042