5-amino-6-benzylpyrazin-2-ol | 1268631-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-amino-6-benzylpyrazin-2-ol
• 英文别名: 5-amino-6-benzyl-1H-pyrazin-2-one
• CAS: 1268631-85-1
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: CAKSMWDFQUYHLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-amino-6-benzylpyrazin-2-ol 在 2-双环己基膦-2',6'-二甲氧基联苯 、 盐酸 、 manganese(IV) oxide 、 palladium diacetate 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 (Z)-8-benzyl-2-(4-methoxybenzylidene)-6-(4-methoxy-phenyl)imidazo[1,2-a]pyrazin-3(2H)-one
  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
• 作为产物：
  描述：

  6-benzyl-5-(4-methylphenylsulfonamido)pyrazin-2-yl 4-methylbenzenesulfonate 在 硫酸 作用下， 以 水 为溶剂， 以85%的产率得到5-amino-6-benzylpyrazin-2-ol
  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

文献信息

• US8431525B2
  申请人：——

  公开号：US8431525B2

  公开（公告）日：2013-04-30
• Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies
  作者：Wong Phakhodee、Mitsuko Toyoda、Chun-Ming Chou、Nisachon Khunnawutmanotham、Minoru Isobe

  DOI：10.1016/j.tet.2010.12.001

  日期：2011.2

  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.