ethyl 4-{4-[(3-amino-6-bromo-2-pyrazinyl)methyl]phenoxy}butanoate | 625848-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 4-{4-[(3-amino-6-bromo-2-pyrazinyl)methyl]phenoxy}butanoate
• 英文别名: Ethyl 4-[4-[(3-amino-6-bromopyrazin-2-yl)methyl]phenoxy]butanoate；ethyl 4-[4-[(3-amino-6-bromopyrazin-2-yl)methyl]phenoxy]butanoate
• CAS: 625848-33-1
• 化学式: C₁₇H₂₀BrN₃O₃
• 分子量: 394.268
• InChiKey: PXSUYHYXMYNOGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-{4-[(3-amino-6-bromo-2-pyrazinyl)methyl]phenoxy}butanoate 在 盐酸 、 二(氰基苯)二氯化钯 、 sodium carbonate 、 1,4-双(二苯基膦)丁烷 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 反应 5.12h， 生成 4-(4-{[2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)-3-oxo-3,7-dihydroimidazo[1,2-a]pyrazin-8-yl]methyl}phenoxy)butanoic acid
  参考文献：
  名称：

  Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties

  摘要：

  A series of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones were prepared from 2-amino-3,5-dibromopyrazine. The concise synthesis of coelenterazine (5j), in three steps, 48% overall yield and >99% purity exemplifies the strategy. Further, the synthetic approach facilitated the regiospecific incorporation of carboxyalkyl linkers on the 3,7-dihydroimidazo[1,2a]pyrazine-3-one nucleus that are required for bioconjugation. Peroxymonocarbonate, an electrophilic oxidant, was used to initiate 'pseudo-flash' chemiluminescence from this class of molecules. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.040
• 作为产物：
  描述：

  4-(叔丁基二甲基甲硅烷基氧基)苄氯 在 四丁基氟化铵 、 sodium hydride 、 magnesium 、 二溴甲烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.53h， 生成 ethyl 4-{4-[(3-amino-6-bromo-2-pyrazinyl)methyl]phenoxy}butanoate
  参考文献：
  名称：

  Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties

  摘要：

  A series of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones were prepared from 2-amino-3,5-dibromopyrazine. The concise synthesis of coelenterazine (5j), in three steps, 48% overall yield and >99% purity exemplifies the strategy. Further, the synthetic approach facilitated the regiospecific incorporation of carboxyalkyl linkers on the 3,7-dihydroimidazo[1,2a]pyrazine-3-one nucleus that are required for bioconjugation. Peroxymonocarbonate, an electrophilic oxidant, was used to initiate 'pseudo-flash' chemiluminescence from this class of molecules. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.040

文献信息

• Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties
  作者：Maciej Adamczyk、Srinivasa Rao Akireddy、Donald D Johnson、Phillip G Mattingly、You Pan、Rajarathnam E Reddy

  DOI：10.1016/j.tet.2003.08.040

  日期：2003.10

  A series of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones were prepared from 2-amino-3,5-dibromopyrazine. The concise synthesis of coelenterazine (5j), in three steps, 48% overall yield and >99% purity exemplifies the strategy. Further, the synthetic approach facilitated the regiospecific incorporation of carboxyalkyl linkers on the 3,7-dihydroimidazo[1,2a]pyrazine-3-one nucleus that are required for bioconjugation. Peroxymonocarbonate, an electrophilic oxidant, was used to initiate 'pseudo-flash' chemiluminescence from this class of molecules. (C) 2003 Elsevier Ltd. All rights reserved.