2-(3-fluorophenylmethyl)-6-(4-hydroxyphenyl)-8-benzyl-3,7-dihydroimidazo[1,2-a]pyrazine-3-one | 423184-49-0

• 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: 2-(3-fluorophenylmethyl)-6-(4-hydroxyphenyl)-8-benzyl-3,7-dihydroimidazo[1,2-a]pyrazine-3-one
• CAS: 423184-49-0
• 化学式: C₂₆H₂₀FN₃O₂
• 分子量: 425.462
• InChiKey: DQSSMDUCPFGBTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  70.91
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(3-fluorophenylmethyl)-6-(4-hydroxyphenyl)-8-benzyl-3,7-dihydroimidazo[1,2-a]pyrazine-3-one 在 manganese(IV) oxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (S)-2-Amino-4-[(R)-2-[[8-benzyl-6-(4-hydroxy-phenyl)-3-oxo-3,7-dihydro-imidazo[1,2-a]pyrazin-2-yl]-(3-fluoro-phenyl)-methylsulfanyl]-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid
  参考文献：
  名称：

  19F-Dehydrocoelenterazine as probe to investigate the active site of symplectin

  摘要：

  Fluorinated dehydrocoelenterazines (F-DCTs) were synthesized to study molecular mechanisms of symplectin; a photoprotein of luminous squid Symplectoteuthis oualaniensis L. F-DCTs reacted with dithiothreitol and glutathione under neutral conditions to give the stable chromophores as symplectin model. Reconstructed symplectin was also obtained by addition of F-DCTs into apo-symplectin, and showed bioluminescence to emit 50-65% amount of light as natural symplectin. The structure of the chromophores was determined by F-19 NMR, Q-TOF-MS, and MS/MS analyses. Sequencing of the chromopeptides of symplectin models prepared from F-DCTs and thiol compounds was accomplished by ESI-Q-TOF-MS/MS analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00100-x
• 作为产物：
  描述：

  3-氟苯乙酸 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 硫酸 、 氢溴酸 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 8.5h， 生成 2-(3-fluorophenylmethyl)-6-(4-hydroxyphenyl)-8-benzyl-3,7-dihydroimidazo[1,2-a]pyrazine-3-one
  参考文献：
  名称：

  19F-Dehydrocoelenterazine as probe to investigate the active site of symplectin

  摘要：

  Fluorinated dehydrocoelenterazines (F-DCTs) were synthesized to study molecular mechanisms of symplectin; a photoprotein of luminous squid Symplectoteuthis oualaniensis L. F-DCTs reacted with dithiothreitol and glutathione under neutral conditions to give the stable chromophores as symplectin model. Reconstructed symplectin was also obtained by addition of F-DCTs into apo-symplectin, and showed bioluminescence to emit 50-65% amount of light as natural symplectin. The structure of the chromophores was determined by F-19 NMR, Q-TOF-MS, and MS/MS analyses. Sequencing of the chromopeptides of symplectin models prepared from F-DCTs and thiol compounds was accomplished by ESI-Q-TOF-MS/MS analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00100-x