1-benzyl-4,5-dibromoimidazole | 101853-78-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-benzyl-4,5-dibromoimidazole
• 英文别名: 1-benzyl-4,5-dibromo-1H-imidazole
• CAS: 101853-78-5
• 化学式: C₁₀H₈Br₂N₂
• 分子量: 315.995
• InChiKey: JNMRXGWQBAWSFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-4,5-dibromoimidazole 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium tetrahydroborate 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 43.0h， 生成 N-苄基咪唑
  参考文献：
  名称：

  NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles

  摘要：

  DOI：

  10.1016/j.molcata.2014.06.012
• 作为产物：
  描述：

  1-苄基-2,4,5-三溴-1H-咪唑 在 乙基溴化镁 作用下， 以 乙醚 为溶剂， 以80%的产率得到1-benzyl-4,5-dibromoimidazole
  参考文献：
  名称：

  噻吩并[2,3- d ]咪唑的简便合成方法

  摘要：

  由咪唑经2,4,5-三生物基咪唑制备4-溴咪唑-5-甲醛的1-保护和1,2-二保护衍生物，并与2-巯基乙酸乙酯反应，得到标题化合物。

  DOI：

  10.1039/c39850001428

文献信息

• Room-Temperature Hydrodehalogenation of Halogenated Heteropentalenes with One or Two Heteroatoms
  作者：Giorgio Chelucci、Salvatore Baldino、Andrea Ruiu

  DOI：10.1021/jo3019335

  日期：2012.11.2

  The pair NaBH4-TMEDA as a hydride source and catalytic PdCl2(4ppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes. with one or two heteroatoms, while Pd(OAc)(2)/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.
• Azoles. Part II. Synthesis of imidazole-2(and -5)-carbaldehydes and derivatives of imidazo[1,2-b]isoquinoline; transmetallation of imidazol-5-yllithium compounds
  作者：Brian Iddon、Anders K. Petersen、Jan Becher、Nils J. Christensen

  DOI：10.1039/p19950001475

  日期：——

  The transmetallations of 1-protected 4-bromoimidazol-5-yllithium derivatives have been studied using DMF as the quenching reagent. 4-Bromoimidazole-2-carbaldehydes are usually the major products and not the -5-carbaldehydes as reported previously. Various attempts to prevent or inhibit these transmetallations are described. Cyclisation of 4-bromo(and 4,5-dibromo)-1-(3,4-dimethoxybenzyl)imidazole-2-carbaldehyde and 1-(3,4-dimethoxybenzyl)benzimidazole-2-carbaldehyde in TFA gave the corresponding imidazo- or benzimidazo-[1,2-b]isoquinoline.
• Iddon, Brian; Khan, Nazir, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1445 - 1452
  作者：Iddon, Brian、Khan, Nazir

  DOI：——

  日期：——
• Iddon Brian, Petersen Anders K., Becher Jan, Christensen Nils J., J. Chem. Soc. Perkin Trans. 1, (1995) N 12, S 1475-1481
  作者：Iddon Brian, Petersen Anders K., Becher Jan, Christensen Nils J.

  DOI：——

  日期：——
• IDDON, B.;KHAN, N.;LIM, BEE, LAM, J. CHEM. SOC. CHEM. COMMUN., 1985, N 20, 1428-1429
  作者：IDDON, B.、KHAN, N.、LIM, BEE, LAM

  DOI：——

  日期：——