8-benzyl-2-(4-hydroxybenzyl)-3-oxo-3,7-dihydroimidazo[1,2-a]pyrazin-6-yl trifluoromethanesulfonate | 1268631-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 英文名称: 8-benzyl-2-(4-hydroxybenzyl)-3-oxo-3,7-dihydroimidazo[1,2-a]pyrazin-6-yl trifluoromethanesulfonate
• 英文别名: [8-benzyl-2-[(4-hydroxyphenyl)methyl]-3-oxo-7H-imidazo[1,2-a]pyrazin-6-yl] trifluoromethanesulfonate
• CAS: 1268631-67-9
• 化学式: C₂₁H₁₆F₃N₃O₅S
• 分子量: 479.436
• InChiKey: RLSCBNOCIFMLGC-UHFFFAOYSA-N

物化性质

• 沸点：
  576.6±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  114.28
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  8-benzyl-2-(4-hydroxybenzyl)-3-oxo-3,7-dihydroimidazo[1,2-a]pyrazin-6-yl trifluoromethanesulfonate 、 4-氟苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以61%的产率得到8-benzyl-6-(4-fluorophenyl)-2-(4-hydroxybenzylidene)-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：

  5-N-(p-toluenesulfonyl)amide-6-benzyl-2-O-trifluoromethanesulfonyloxy-pyrazine 在 盐酸 、 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 8-benzyl-2-(4-hydroxybenzyl)-3-oxo-3,7-dihydroimidazo[1,2-a]pyrazin-6-yl trifluoromethanesulfonate
  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

• 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.