(E)-2-(2-bromostyryl)-1H-benzo[d]imidazole | 783341-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (E)-2-(2-bromostyryl)-1H-benzo[d]imidazole
• 英文别名: 2-[(E)-2-(2-bromophenyl)ethenyl]-1H-benzimidazole
• CAS: 783341-21-9
• 化学式: C₁₅H₁₁BrN₂
• 分子量: 299.17
• InChiKey: AZZXEOCXDOEVPQ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  邻溴苯甲醛 在 copper(l) iodide 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (E)-2-(2-bromostyryl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  α-Aroylidineketene dithioacetal chemistry: CuI catalyzed synthesis of 2-styryl benzimidazoles enroute to regioselective hydrothiolation

  摘要：

  Reactivity of alpha-aroylidineketene dithioacetals 2 was investigated to synthesize novel 2-styrylbenzimidazole derivatives 4 and their hydrothiolated product 2-(2-(methylthio)-2-arylethyl)-1H-benzoidlimidazoles 5 has been reported. Compounds 4 and 5 were synthesized by cyclocondensation of alpha-aroylidineketene dithioacetals 2 and o-phenylene diamine (OPD) 3 in the presence and absence of copper catalyst respectively. Regioselective one-pot tandem hydrothiolation of olefin functionality in 4 was achieved under AcOH conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.008

文献信息

• From a Multipotent Stilbene to Soluble Epoxide Hydrolase Inhibitors with Antiproliferative Properties
  作者：Estel.la Buscató、Dominik Büttner、Astrid Brüggerhoff、Franca-Maria Klingler、Julia Weber、Bastian Scholz、Aleksandra Živković、Rolf Marschalek、Holger Stark、Dieter Steinhilber、Helge B. Bode、Ewgenij Proschak

  DOI：10.1002/cmdc.201300057

  日期：2013.6

  Inspired by nature: Natural product isopropylstilbene was identified as an inhibitor of soluble epoxide hydrolase exhibiting antiproliferative properties. Following the natural product inspired design approach, a library of (E)‐styryl‐1H‐benzo[d]imidazoles was synthesized and evaluated with recombinant enzyme and on several cancer cell lines.

  受自然界的启发：天然产物异丙基苯乙烯被鉴定为具有抗增殖特性的可溶性环氧化物水解酶的抑制剂。遵循天然产物的设计方法，合成了（E）-styryl-1 H-苯并[ d ]咪唑文库，并用重组酶和在几种癌细胞系上进行了评估。
• α-Aroylidineketene dithioacetal chemistry: CuI catalyzed synthesis of 2-styryl benzimidazoles enroute to regioselective hydrothiolation
  作者：Pandi Dhanalakshmi、Sivakumar Shanmugam

  DOI：10.1016/j.tet.2015.06.008

  日期：2015.9

  Reactivity of alpha-aroylidineketene dithioacetals 2 was investigated to synthesize novel 2-styrylbenzimidazole derivatives 4 and their hydrothiolated product 2-(2-(methylthio)-2-arylethyl)-1H-benzoidlimidazoles 5 has been reported. Compounds 4 and 5 were synthesized by cyclocondensation of alpha-aroylidineketene dithioacetals 2 and o-phenylene diamine (OPD) 3 in the presence and absence of copper catalyst respectively. Regioselective one-pot tandem hydrothiolation of olefin functionality in 4 was achieved under AcOH conditions. (C) 2015 Elsevier Ltd. All rights reserved.