ethyl 4-(4-{[3-amino-6-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-2-pyrazinyl]methyl}phenoxy)butanoate | 625848-41-1

• 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-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-2-pyrazinyl]methyl}phenoxy)butanoate
• 英文别名: Ethyl 4-[4-[[3-amino-6-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]pyrazin-2-yl]methyl]phenoxy]butanoate；ethyl 4-[4-[[3-amino-6-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]pyrazin-2-yl]methyl]phenoxy]butanoate
• CAS: 625848-41-1
• 化学式: C₂₉H₃₉N₃O₄Si
• 分子量: 521.732
• InChiKey: XHMMCVOULPKTGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  96.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1,1-diethoxypropan-2-one 、 ethyl 4-(4-{[3-amino-6-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-2-pyrazinyl]methyl}phenoxy)butanoate 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以32%的产率得到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 二(氰基苯)二氯化钯 、 四丁基氟化铵 、 sodium hydride 、 sodium carbonate 、 magnesium 、 1,4-双(二苯基膦)丁烷 、 二溴甲烷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.65h， 生成 ethyl 4-(4-{[3-amino-6-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-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.