(Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one oxime | 1350850-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one oxime
• 英文别名: (Z)-1-tert-butyl-2-(1H-1,2,4-triazol-1-yl)ethanone oxime；3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one oxime；(NZ)-N-[3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ylidene]hydroxylamine
• CAS: 1350850-60-0
• 化学式: C₈H₁₄N₄O
• 分子量: 182.225
• InChiKey: YOHXSIRUWOBUFZ-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one oxime 在 potassium carbonate 、 一水合肼 、 溶剂黄146 、 potassium iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 6.08h， 生成 (E)-2-((Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ylideneaminooxy)-N′-(3-methoxybenzylidene)acetohydrazide
  参考文献：
  名称：

  微波辅助酰基hydr衍生物作为流感神经氨酸酶抑制剂的合成，表征和生物测定

  摘要：

  通过微波辐照合成了一系列hydr derivatives衍生物（4a - 4s），反应时间短，产率高。通过单晶X射线衍射进一步确定化合物4j的晶体结构。在体外评估所有衍生物的流感神经氨酸酶抑制活性。其中，化合物4l和4n表现出最强的活性，IC 50值分别为59.86和49.97μM。进行了分子对接以研究蛋白质与化合物4n之间的相互作用。对接结果揭示了标题化合物的潜在双位点结合模型（“ 430腔-Linker-SA腔”模型），这为新型流感神经氨酸酶抑制剂的设计提供了新思路。

  DOI：

  10.1007/s00044-017-2015-6
• 作为产物：
  描述：

  3,3-二甲基-1-(1H-1,2,4-三唑-1-基)丁-2-酮 在 盐酸羟胺 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以89%的产率得到(Z)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one oxime
  参考文献：
  名称：

  Synthesis and Fungicidal Activity of(1Z, 3Z)-4,4-Dimethyl-1-substitutedphenyl-2-(1H-1,2,4-triazol-1-yl)-pent-1-en-3-oneO-[2,4-dimethylthiazole(or 4-methyl-1,2,3-thiadiazole)]-5-carbonyl Oximes

  摘要：

  A series of novel (Z)‐1‐tert‐butyl (or phenyl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)‐ethanoneO‐[2,4‐dimethylthiazole (or 4‐methyl‐1,2,3‐thiadiazole) −5‐carbonyl] oximes5a–5cand (1Z, 3Z)‐4,4‐dimethyl‐1‐substitutedphenyl‐2‐(1H‐1,2,4‐triazol‐1‐yl)‐pent‐1‐en‐3‐oneO‐[2,4‐dimethylthiazole (or 4‐methyl‐1,2,3‐thiadiazole)‐5‐carbonyl] oximes6a–6ewere synthesized by the condensations of (Z)‐1‐tert‐butyl (or phenyl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)‐ethanone oximes3or (1Z, 3Z)‐4,4‐dimethyl‐1‐substitutedphenyl‐2‐(1H‐1,2,4‐triazol‐1‐yl)‐pent‐1‐en‐3‐one oximes4with 2,4‐dimethylthiazole‐5‐carbonyl chloride or 4‐methyl‐1,2,3‐thiadiazole‐5‐carbonyl chloride in the basic condition. Their structures were confirmed by IR,1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays showed the title compounds5and6exhibited moderate to good fungicidal activities. For example, compound6cpossessed 86.4% inhibition againstFusarium oxysporum, and compound6bexhibited 86.4 and 100% inhibition againstFusarium oxysporumandCercospora arachidicola Horiat the concentration of 50 mg/L, respectively.

  DOI：

  10.1002/jhet.783

文献信息

• Microwave-assisted synthesis, characterization and bioassay of acylhydrazone derivatives as influenza neuraminidase inhibitors
  作者：Mengwu Xiao、Jiao Ye、Wenwen Lian、Meng Zhang、Beibei Li、Ailin Liu、Aixi Hu

  DOI：10.1007/s00044-017-2015-6

  日期：2017.12

  A series of acylhydrazone derivatives (4a–4s) were synthesized via microwave irradiation with short reaction time and good yields. The crystal structure of compound 4j was further determined by single-crystal X-ray diffraction. All of the derivatives were evaluated in vitro for influenza neuraminidase inhibitory activities. Among them, compounds 4l and 4n showed the most potent activity with IC50 values

  通过微波辐照合成了一系列hydr derivatives衍生物（4a - 4s），反应时间短，产率高。通过单晶X射线衍射进一步确定化合物4j的晶体结构。在体外评估所有衍生物的流感神经氨酸酶抑制活性。其中，化合物4l和4n表现出最强的活性，IC 50值分别为59.86和49.97μM。进行了分子对接以研究蛋白质与化合物4n之间的相互作用。对接结果揭示了标题化合物的潜在双位点结合模型（“ 430腔-Linker-SA腔”模型），这为新型流感神经氨酸酶抑制剂的设计提供了新思路。
• Synthesis and Fungicidal Activity of<i>(1Z, 3Z)-</i>4,4-Dimethyl-1-substitutedphenyl-2-(1<i>H</i>-1,2,4-triazol-1-yl)-pent-1-en-3-one<i>O</i>-[2,4-dimethylthiazole(or 4-methyl-1,2,3-thiadiazole)]-5-carbonyl Oximes
  作者：Hui-Yu Mao、Hong Song、De-Qing Shi

  DOI：10.1002/jhet.783

  日期：2012.5

  A series of novel (Z)‐1‐tert‐butyl (or phenyl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)‐ethanoneO‐[2,4‐dimethylthiazole (or 4‐methyl‐1,2,3‐thiadiazole) −5‐carbonyl] oximes5a–5cand (1Z, 3Z)‐4,4‐dimethyl‐1‐substitutedphenyl‐2‐(1H‐1,2,4‐triazol‐1‐yl)‐pent‐1‐en‐3‐oneO‐[2,4‐dimethylthiazole (or 4‐methyl‐1,2,3‐thiadiazole)‐5‐carbonyl] oximes6a–6ewere synthesized by the condensations of (Z)‐1‐tert‐butyl (or phenyl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)‐ethanone oximes3or (1Z, 3Z)‐4,4‐dimethyl‐1‐substitutedphenyl‐2‐(1H‐1,2,4‐triazol‐1‐yl)‐pent‐1‐en‐3‐one oximes4with 2,4‐dimethylthiazole‐5‐carbonyl chloride or 4‐methyl‐1,2,3‐thiadiazole‐5‐carbonyl chloride in the basic condition. Their structures were confirmed by IR,1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays showed the title compounds5and6exhibited moderate to good fungicidal activities. For example, compound6cpossessed 86.4% inhibition againstFusarium oxysporum, and compound6bexhibited 86.4 and 100% inhibition againstFusarium oxysporumandCercospora arachidicola Horiat the concentration of 50 mg/L, respectively.