(Z)-8-benzyl-2-(4-methoxybenzylidene)-6-(4-methoxy-phenyl)imidazo[1,2-a]pyrazin-3(2H)-one | 276879-72-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-8-benzyl-2-(4-methoxybenzylidene)-6-(4-methoxy-phenyl)imidazo[1,2-a]pyrazin-3(2H)-one
• 英文别名: (2Z)-8-benzyl-6-(4-methoxyphenyl)-2-[(4-methoxyphenyl)methylidene]imidazo[1,2-a]pyrazin-3-one
• CAS: 276879-72-2
• 化学式: C₂₈H₂₃N₃O₃
• 分子量: 449.509
• InChiKey: IYOHFUOBGMVYBD-UQQQWYQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-methoxyphenyl)methyl-1,3-dithiane 在 2-双环己基膦-2',6'-二甲氧基联苯 、 盐酸 、 manganese(IV) oxide 、 N-氯代丁二酰亚胺 、 正丁基锂 、 水 、 palladium diacetate 、 caesium carbonate 、 对甲苯磺酸 、 silver nitrate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 19.08h， 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

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.