N-methyl-3-ethyl-4-amino-1H-pyrazole-5-carboxamide | 1340597-33-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methyl-3-ethyl-4-amino-1H-pyrazole-5-carboxamide
• 英文别名: 4-amino-5-ethyl-N-methyl-1H-pyrazole-3-carboxamide
• CAS: 1340597-33-2
• 化学式: C₇H₁₂N₄O
• 分子量: 168.198
• InChiKey: GMIPPEFMUVYBCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (s)-3-methyl-4-nitro-1H-pyrazole-5-carbonyl chloride 、 N-methyl-3-ethyl-4-amino-1H-pyrazole-5-carboxamide 在 三乙胺 作用下， 反应 8.0h， 以69%的产率得到3-ethyl-N-methyl-4-(3-methyl-4-nitro-1H-pyrazole-5-carboxamido)-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Synthesis and anti-TMV activity of novel N-(3-alkyl-1H-pyrazol-4-yl)-3-alkyl-4-substituted-1H-pyrazole-5-carboxamides

  摘要：

  In order to investigate the biological activity of novel bis-pyrazole compounds, a series of N-(3-alkyl-5-(N-methylcarbamyl)-1 H-pyrazol-4-yl)-3-alkyl-4-substituted-1H-pyrazole-5-carboxamides were designed and synthesized with ethyl 3-alkyl-1H-pyrazole-5-carboxylate 1 as starting materials. N-Methyl-3-alkyl-4-amino-1H-pyrazole-5-carboxamides 6 were obtained from 1 via 5 steps. 3-Alkyl-4-substitued-1H-pyrazole-5-carboxyl chlorides 4a, 4b, 11a, 11b, 11c or 12 were also obtained from 1 via several steps. Target compounds 7a-7g were obtained after the reaction of 6 with the above 1H-pyrazole-5-carboxyl chlorides. Preliminary bioassay showed some compounds possessing good inactivation effect against TMV (tobacco mosaic virus). Compound 7a showed higher activity superior to ningnanmycin at a concentration of 5.0 x 10(-4) g/mL and equal activity it 1.0 x 10(-4) g/mL; 7b and 7c showed equal activity to virazole both at concentrations of 5.0 x 10(-4) g/mL and 1.0 x 10(-4) g/ML. (C) 2012 De Kai Yuan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.04.010
• 作为产物：
  描述：

  N-methyl-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 75.0 ℃ 、1.0 MPa 条件下， 反应 2.0h， 生成 N-methyl-3-ethyl-4-amino-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  一类含1,2,3-噻二唑的吡唑双酰胺类化合物 及其合成方法与应用

  摘要：

  本发明公开了属于有机合成技术领域的一类含1,2,3‑噻二唑的吡唑双酰胺类化合物及其合成方法与应用，该化合物具有通式I所述的结构。制备该化合物时，首先合成4‑氨基吡唑中间体和1,2,3‑噻二唑甲酰氯中间体，然后按照常规的缩合反应条件，将两者进行缩合，即可合成通式I化合物。该类化合物均具有优良的杀蚊幼虫活性和一定的杀粘虫活性，部分化合物具有抗烟草花叶病毒活性和杀菌活性；该类化合物结构新颖、修饰改造余地大、制备方法合理易行，可作为农药活性先导进行深入研究，而且可作为杀蚊剂予以应用，具有潜在的生产应用价值。

  公开号：

  CN105037346B

文献信息

• 一类含1,2,3-噻二唑的吡唑双酰胺类化合物 及其合成方法与应用
  申请人：中国农业大学

  公开号：CN105037346B

  公开（公告）日：2017-12-22

  本发明公开了属于有机合成技术领域的一类含1,2,3‑噻二唑的吡唑双酰胺类化合物及其合成方法与应用，该化合物具有通式I所述的结构。制备该化合物时，首先合成4‑氨基吡唑中间体和1,2,3‑噻二唑甲酰氯中间体，然后按照常规的缩合反应条件，将两者进行缩合，即可合成通式I化合物。该类化合物均具有优良的杀蚊幼虫活性和一定的杀粘虫活性，部分化合物具有抗烟草花叶病毒活性和杀菌活性；该类化合物结构新颖、修饰改造余地大、制备方法合理易行，可作为农药活性先导进行深入研究，而且可作为杀蚊剂予以应用，具有潜在的生产应用价值。
• Synthesis and anti-TMV activity of novel N-(3-alkyl-1H-pyrazol-4-yl)-3-alkyl-4-substituted-1H-pyrazole-5-carboxamides
  作者：Da Qiang Zhang、Gao Fei Xu、Zhi Jin Fan、Dao Quan Wang、Xin Ling Yang、De Kai Yuan

  DOI：10.1016/j.cclet.2012.04.010

  日期：2012.6

  In order to investigate the biological activity of novel bis-pyrazole compounds, a series of N-(3-alkyl-5-(N-methylcarbamyl)-1 H-pyrazol-4-yl)-3-alkyl-4-substituted-1H-pyrazole-5-carboxamides were designed and synthesized with ethyl 3-alkyl-1H-pyrazole-5-carboxylate 1 as starting materials. N-Methyl-3-alkyl-4-amino-1H-pyrazole-5-carboxamides 6 were obtained from 1 via 5 steps. 3-Alkyl-4-substitued-1H-pyrazole-5-carboxyl chlorides 4a, 4b, 11a, 11b, 11c or 12 were also obtained from 1 via several steps. Target compounds 7a-7g were obtained after the reaction of 6 with the above 1H-pyrazole-5-carboxyl chlorides. Preliminary bioassay showed some compounds possessing good inactivation effect against TMV (tobacco mosaic virus). Compound 7a showed higher activity superior to ningnanmycin at a concentration of 5.0 x 10(-4) g/mL and equal activity it 1.0 x 10(-4) g/mL; 7b and 7c showed equal activity to virazole both at concentrations of 5.0 x 10(-4) g/mL and 1.0 x 10(-4) g/ML. (C) 2012 De Kai Yuan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.