2,4,5-tribromo-1-(4-methoxybenzyl)-1H-imidazole | 101901-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4,5-tribromo-1-(4-methoxybenzyl)-1H-imidazole
• 英文别名: 1-(4-methoxybenzyl)-2,4,5-tribromoimidazole；2,4,5-tribromo-1-(4-methoxybenzyl)imidazole；2,4,5-tribromo-1-[(4-methoxyphenyl)methyl]-1H-imidazole；2,4,5-tribromo-1-[(4-methoxyphenyl)methyl]imidazole
• CAS: 101901-58-0
• 化学式: C₁₁H₉Br₃N₂O
• 分子量: 424.917
• InChiKey: DPDZWBOJMFBQTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,5-tribromo-1-(4-methoxybenzyl)-1H-imidazole 在 三氟乙酸 作用下， 反应 7.0h， 以93%的产率得到2,4,5-三溴咪唑
  参考文献：
  名称：

  Iddon, Brian; Khan, Nazir; Lim, Bee Lan, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1437 - 1444

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,5-三溴咪唑 、 4-甲氧基氯苄 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到2,4,5-tribromo-1-(4-methoxybenzyl)-1H-imidazole
  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

• Application of a 6π-1-Azatriene Electrocyclization Strategy to the Total Synthesis of the Marine Sponge Metabolite Ageladine A and Biological Evaluation of Synthetic Analogues
  作者：Matthew L. Meketa、Steven M. Weinreb、Yoichi Nakao、Nobuhiro Fusetani

  DOI：10.1021/jo0707232

  日期：2007.6.1

  A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki−Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this

  据报道，具有血管生成抑制作用的海洋代谢产物法拉定A的12步合成。关键步骤包括用于形成吡啶环的6π-1-氮杂三烯电环化以及N -Boc-吡咯-2-硼酸与氯咪唑并吡啶的Suzuki-Miyaura偶联。另外，描述了在该合成过程中制备的多种拉德金定A的合成类似物的生物活性的评估。
• Total Synthesis of Ageladine A, an Angiogenesis Inhibitor from the Marine Sponge <i>Agelas nakamurai</i>
  作者：Matthew L. Meketa、Steven M. Weinreb

  DOI：10.1021/ol0602304

  日期：2006.3.1

  A 12-step total synthesis of the tricyclic heteroaromatic marine metabolite ageladine A has been achieved using a 6 pi-azaelectrocyclization and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloropyridine as key steps.
• 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.
• Selective Sequential Cross-Coupling Reactions on Imidazole towards Neurodazine and Analogues
  作者：Michael Schnürch、Marko Mihovilovic、Lisa-Maria Recnik、Mohammed Abd El Hameid、Maximilian Haider

  DOI：10.1055/s-0032-1316906

  日期：——

  Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki-Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.
• 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：——