2-cyano-5-methoxy-1-methylbenzimidazole | 1373421-52-3

• 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: 2-cyano-5-methoxy-1-methylbenzimidazole
• 英文别名: 5-methoxy-1-methylbenzimidazole-2-carbonitrile
• CAS: 1373421-52-3
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: CUNKVOVDFCQJOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-甲氧基邻苯二胺 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 6-methoxy-1-methylbenzimidazole-2-carbonitrile 、 2-cyano-5-methoxy-1-methylbenzimidazole
  参考文献：
  名称：

  Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging

  摘要：

  Bioluminescence imaging with luciferase enzymes requires access to light-emitting, small-molecule luciferins. Here, we describe a rapid method to synthesize n-luciferin, the substrate for firefly luciferase (Fluc), along with a novel set of electronically modified analogues. Our procedure utilizes a relatively rare, but synthetically useful dithiazolium reagent to generate heteroaromatic scaffolds in a divergent fashion. Two of the luciferin analogues produced with this approach emit light with Flue in vitro and in live cells. Collectively, our work increases the number of substrates that can be used for bioluminescence imaging and provides a general strategy for synthesizing new collections of luciferins.

  DOI：

  10.1021/ja301493d

文献信息

• Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging
  作者：David C. McCutcheon、Miranda A. Paley、Rachel C. Steinhardt、Jennifer A. Prescher

  DOI：10.1021/ja301493d

  日期：2012.5.9

  Bioluminescence imaging with luciferase enzymes requires access to light-emitting, small-molecule luciferins. Here, we describe a rapid method to synthesize n-luciferin, the substrate for firefly luciferase (Fluc), along with a novel set of electronically modified analogues. Our procedure utilizes a relatively rare, but synthetically useful dithiazolium reagent to generate heteroaromatic scaffolds in a divergent fashion. Two of the luciferin analogues produced with this approach emit light with Flue in vitro and in live cells. Collectively, our work increases the number of substrates that can be used for bioluminescence imaging and provides a general strategy for synthesizing new collections of luciferins.