3-benzyl-5-(6-methoxynaphthalen-2-yl)pyrazin-2-amine | 1268631-78-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-benzyl-5-(6-methoxynaphthalen-2-yl)pyrazin-2-amine
• CAS: 1268631-78-2
• 化学式: C₂₂H₁₉N₃O
• 分子量: 341.412
• InChiKey: QZSNPMZZZJHIRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-benzyl-6-oxo-1H-pyrazin-3-yl)-4-methylbenzenesulfonamide 在 potassium phosphate 、 四(三苯基膦)钯 、 硫酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-benzyl-5-(6-methoxynaphthalen-2-yl)pyrazin-2-amine
  参考文献：
  名称：

  Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies

  摘要：

  Synthesis of coelenterazine analogs is in recent demand to supply more luminescent compounds with reasonable stability as substrate for the photoprotein manipulated in a living cells or particular organelle. There are limited methods for the synthesis of 6-substituted coelenterazine due to the route and instability of the compounds under the existing conditions. This paper describes six examples including Suzuki-Miyaura cross coupling reaction with reactive triflate (unstable) and stable tosylate intermediates of the imidazo[1,2-a]pyrazin-3-one. Five examples of 2-amino-3-benzyl-5-O-Tf-pyrazine are also discussed. The product coelenterazine analogs are obtained in the form of dehydrocoelenterazine, which is the substrate of a squid photoprotein, symplectin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.001