3-benzyl-5-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-3-phenyl-2-pyrazinamine | 353497-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzyl-5-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-3-phenyl-2-pyrazinamine
• 英文别名: 3-benzyl-5-[4-(tert-butyldimethylsiloxy)phenyl]pyrazin-2-amine；3-Benzyl-5-[4-(tert-butyldimethylsilyloxy)phenyl]pyrazin-2-amine；3-benzyl-5-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]pyrazin-2-amine
• CAS: 353497-17-3
• 化学式: C₂₃H₂₉N₃OSi
• 分子量: 391.588
• InChiKey: PBRWROSEWMHKDM-UHFFFAOYSA-N

物化性质

• 熔点：
  98-101 °C
• 沸点：
  477.4±45.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-[4-(3,3-diethoxy-2-oxopropyl)phenoxy]butanoate 、 3-benzyl-5-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-3-phenyl-2-pyrazinamine 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以56%的产率得到4-(4-{[8-benzyl-6-(4-hydroxyphenyl)-3-oxo-3,7-dihydroimidazo[1,2-a]pyrazin-2-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-(叔丁基二甲基硅氧基)苯基硼酸 、 2-氨基-3-(苯基甲基)-5-溴吡嗪 在 二(氰基苯)二氯化钯 、 sodium carbonate 、 1,4-双(二苯基膦)丁烷 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 0.12h， 以98%的产率得到3-benzyl-5-(4-[tert-butyl(dimethyl)silyloxy]phenyl)-3-phenyl-2-pyrazinamine
  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

• Strategies for Large-Scale Synthesis of Coelenterazine for in Vivo Applications
  作者：Tej Shrestha、Stefan Bossmann、Deryl Troyer

  DOI：10.1055/s-0033-1340556

  日期：——

  A new application of two Negishi-type coupling reactions for the synthesis of coelenterazine is reported. The synthesis of coelenterazine in high purity on a gram scale will enable numerous approaches to bioluminescence imaging and possibly photodynamic therapy of deep-seated tumors. Coelenterazine is the substrate for several luciferases, among them Gaussia luciferase (gLuc). This synthesis starts with pyrazin-2-amine and uses inexpensive starting materials and catalysts.