methyl (Z)-2-(hydroxyimino)-3-(1H-1,2,4-triazol-1-yl)butanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-2-(hydroxyimino)-3-(1H-1,2,4-triazol-1-yl)butanoate
• 英文别名: methyl (2Z)-2-hydroxyimino-3-(1,2,4-triazol-1-yl)butanoate
• 化学式: C₇H₁₀N₄O₃
• 分子量: 198.181
• InChiKey: KOBPDLJFBSWUNX-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(三甲硅基)-1H-1,2,4-三唑 、 methyl (E)-2-[bis(trimethylsilyloxy)amino]but-2-enoate 在 三乙胺 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 25.0h， 生成 methyl (E)-2-(hydroxyimino)-3-(1H-1,2,4-triazol-1-yl)butanoate 、 methyl (Z)-2-(hydroxyimino)-3-(1H-1,2,4-triazol-1-yl)butanoate 、 methyl (E)-2-(hydroxyimino)-3-(4H-1,2,4-triazol-4-yl)butanoate
  参考文献：
  名称：

  Chemistry of N,N-Bis(silyloxy)enamines, Part 5

  摘要：

  Aliphatic nitro compounds can be considered as good precursors of a wide variety of alpha-azolyl-substituted oximes. The double silylation of convenient aliphatic nitro compounds and the subsequent N,C-coupling of the resulting N,N-bis(silyloxy)enamines 3 with N-silylated azoles 4 lead to the formation of the silylated alpha-azolyl-substituted oximes 6, which can be smoothly desilylated to give the target a-azolyl-substituted oximes 5. The mechanism of the key step of this process -N,C-coupling - includes the generation of corresponding conjugated nitrosoalkenes 7 (Schemes 4 and 5). The contribution of the chain mechanism in the overall process is considered as well. The studies of the scope and limitations of this reaction, as well as the optimization of its conditions were accomplished. The configuration of the C=N bond in oximes was established by NMR.

  DOI：

  10.1002/1522-2675(200210)85:10<3489::aid-hlca3489>3.0.co;2-6

文献信息

• Chemistry of N,N-Bis(silyloxy)enamines, Part 5
  作者：Alexey V. Lesiv、Sema L. Ioffe、Yury A. Strelenko、Vladimir A. Tartakovsky

  DOI：10.1002/1522-2675(200210)85:10<3489::aid-hlca3489>3.0.co;2-6

  日期：2002.10

  Aliphatic nitro compounds can be considered as good precursors of a wide variety of alpha-azolyl-substituted oximes. The double silylation of convenient aliphatic nitro compounds and the subsequent N,C-coupling of the resulting N,N-bis(silyloxy)enamines 3 with N-silylated azoles 4 lead to the formation of the silylated alpha-azolyl-substituted oximes 6, which can be smoothly desilylated to give the target a-azolyl-substituted oximes 5. The mechanism of the key step of this process -N,C-coupling - includes the generation of corresponding conjugated nitrosoalkenes 7 (Schemes 4 and 5). The contribution of the chain mechanism in the overall process is considered as well. The studies of the scope and limitations of this reaction, as well as the optimization of its conditions were accomplished. The configuration of the C=N bond in oximes was established by NMR.