5,7,8-trifluoro-1,4-dimethyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine | 865860-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,7,8-trifluoro-1,4-dimethyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine
• 英文别名: 5,7,8-Trifluoro-1,4-dimethyl-2,3-dihydropyrido[3,4-b]pyrazine
• CAS: 865860-86-2
• 化学式: C₉H₁₀F₃N₃
• 分子量: 217.194
• InChiKey: HAJMFLFLPRSEKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,7,8-trifluoro-1,4-dimethyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine 在 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 186.0h， 生成 5-butyl-8-fluoro-7-methoxy-1,4-dimethyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine
  参考文献：
  名称：

  Tetrahydropyrido[3,4-b]pyrazine Scaffolds from Pentafluoropyridine

  摘要：

  Representative polyfunctional tetrahydropyrido[3,4-b]pyrazine scaffolds have been synthesized very readily by a one-pot annelation reaction of pentafluoropyridine with appropriate diamines. The trifluorinated pyridopyrazine products react sequentially with various nucleophiles to give polysubstituted tetrahydropyridopyrazines, demonstrating the potential of the polyfluorinated ring fused pyridine system as a scaffold for the synthesis of previously inaccessible polysubstituted pyridopyrazine derivatives. This general approach has special relevance to the development of new chemical entities for the life science industries and particularly in the drug discovery arena, in which low molecular weight, polyfunctional heterocyclic derivatives are playing an increasingly important role.

  DOI：

  10.1021/jo0508696
• 作为产物：
  描述：

  五氟吡啶 、 N,N'-二甲基乙二胺 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以97%的产率得到5,7,8-trifluoro-1,4-dimethyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine
  参考文献：
  名称：

  Tetrahydropyrido[3,4-b]pyrazine Scaffolds from Pentafluoropyridine

  摘要：

  Representative polyfunctional tetrahydropyrido[3,4-b]pyrazine scaffolds have been synthesized very readily by a one-pot annelation reaction of pentafluoropyridine with appropriate diamines. The trifluorinated pyridopyrazine products react sequentially with various nucleophiles to give polysubstituted tetrahydropyridopyrazines, demonstrating the potential of the polyfluorinated ring fused pyridine system as a scaffold for the synthesis of previously inaccessible polysubstituted pyridopyrazine derivatives. This general approach has special relevance to the development of new chemical entities for the life science industries and particularly in the drug discovery arena, in which low molecular weight, polyfunctional heterocyclic derivatives are playing an increasingly important role.

  DOI：

  10.1021/jo0508696

文献信息

• Synthesis of tetrahydropyrido[2,3-b]pyrazine scaffolds from 2,3,5,6-tetrafluoropyridine derivatives
  作者：Christopher A. Hargreaves、Graham Sandford、Rachel Slater、Dmitrii S. Yufit、Judith A.K. Howard、Antonio Vong

  DOI：10.1016/j.tet.2007.03.164

  日期：2007.6

  Reactions between N,N′-dimethylethylene diamine and a range of 2,3,5,6-tetrafluoropyridine derivatives provided ready access to the corresponding tetrahydropyrido[2,3-b]pyrazine systems if the substituent located at the 4-position of the pyridine ring was either hydrogen or an electron withdrawing substituent. In contrast, the presence of electron donating substituents at the 4-position made the formation

  N，N'-二甲基乙二胺与各种2,3,5,6-四氟吡啶衍生物之间的反应可以使相应的四氢吡啶并[2,3- b ]吡嗪系统易于接近，前提是该取代基位于相应的四氢吡啶并[2,3- b ]吡嗪系统上。吡啶环是氢或吸电子取代基。相反，在4位上存在供电子性取代基使得形成环稠合产物更加困难。五氟吡啶的两步顺序亲核取代程序为合成生命科学发现领域感兴趣的多官能四氢吡啶并[2,3- b ]吡嗪支架提供了方便且适用的方法。
• Tetrahydropyrido[3,4-<i>b</i>]pyrazine Scaffolds from Pentafluoropyridine
  作者：Graham Sandford、Rachel Slater、Dmitrii S. Yufit、Judith A. K. Howard、Antonio Vong

  DOI：10.1021/jo0508696

  日期：2005.9.1

  Representative polyfunctional tetrahydropyrido[3,4-b]pyrazine scaffolds have been synthesized very readily by a one-pot annelation reaction of pentafluoropyridine with appropriate diamines. The trifluorinated pyridopyrazine products react sequentially with various nucleophiles to give polysubstituted tetrahydropyridopyrazines, demonstrating the potential of the polyfluorinated ring fused pyridine system as a scaffold for the synthesis of previously inaccessible polysubstituted pyridopyrazine derivatives. This general approach has special relevance to the development of new chemical entities for the life science industries and particularly in the drug discovery arena, in which low molecular weight, polyfunctional heterocyclic derivatives are playing an increasingly important role.