N-butyl-6,7-dimethyl-3-[3-(trifluoromethoxy)phenyl]quinoxaline-2-carboxamide | 1609463-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-butyl-6,7-dimethyl-3-[3-(trifluoromethoxy)phenyl]quinoxaline-2-carboxamide
• CAS: 1609463-96-8
• 化学式: C₂₂H₂₂F₃N₃O₂
• 分子量: 417.431
• InChiKey: SFDLLSXQDIEJQA-UHFFFAOYSA-N

物化性质

• 沸点：
  532.9±50.0 °C(predicted)
• 密度：
  1.234±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 水 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 生成 N-butyl-6,7-dimethyl-3-[3-(trifluoromethoxy)phenyl]quinoxaline-2-carboxamide
  参考文献：
  名称：

  Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

  摘要：

  This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a 'convertible carboxylic acid', which in addition may be captured in an intramolecular sense to generate structurally complex 2-benzimidazolylquinoxalines in a mere two steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.013

文献信息

• A Robust Protocol for the Synthesis of Quinoxalines and 5H-Benzo[e][1,4]di­azepines via the Acidless Ugi Reaction
  作者：Christopher Hulme、Muhammad Ayaz、Guillermo Martinez-Ariza

  DOI：10.1055/s-0033-1339135

  日期：——

  Concise two-step, one-pot protocols for the syntheses of quinoxalines and 5H-benzo[e][1,4]diazepines are reported. An acidless' Ugi reaction followed by a Boc-deprotection-cyclization sequence is shown to produce arrays of both functionalized scaffolds in good yield. Mono-N-Boc-protected diamines are employed to access quinoxalines and an analogous benzylic amine affords access to 5H-benzo[e][1,4]diazepines in conjunction with supporting reagents in the acidless' Ugi reaction. Both methodologies are robust, straightforward, and allow installation of at least three points of diversity in the resulting scaffolds.
• Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction
  作者：Muhammad Ayaz、Zhigang Xu、Christopher Hulme

  DOI：10.1016/j.tetlet.2014.04.013

  日期：2014.6

  This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a 'convertible carboxylic acid', which in addition may be captured in an intramolecular sense to generate structurally complex 2-benzimidazolylquinoxalines in a mere two steps. (C) 2014 Elsevier Ltd. All rights reserved.