1,3-Dimethyl-5-(3-nitro-phenoxy)-1H-pyrazole-4-carbaldehyde | 889867-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Dimethyl-5-(3-nitro-phenoxy)-1H-pyrazole-4-carbaldehyde
• 英文别名: 1,3-Dimethyl-5-(3-nitrophenoxy)pyrazole-4-carbaldehyde
• CAS: 889867-90-7
• 化学式: C₁₂H₁₁N₃O₄
• 分子量: 261.237
• InChiKey: ITZFKEMSJGLGNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-Dimethyl-5-(3-nitro-phenoxy)-1H-pyrazole-4-carbaldehyde 在 盐酸羟胺 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1,3-dimethyl-5-(3-nitrophenoxy)-1H-pyrazole-4-carbaldehyde O-(4-((2-chlorothiazol-5-yl)methoxy)benzyl) oxime
  参考文献：
  名称：

  The thiazoylmethoxy modification on pyrazole oximes: Synthesis and insecticidal biological evaluation beyond acaricidal activity

  摘要：

  DOI：

  10.1016/j.cclet.2014.06.011
• 作为产物：
  描述：

  1,3-二甲基-5-吡唑酮 在 三氯氧磷 作用下， 生成 1,3-Dimethyl-5-(3-nitro-phenoxy)-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  Stereoselective Synthesis and Antifungal Activities of (E)-α-(Methoxyimino)benzeneacetate Derivatives Containing 1,3,5-Substituted Pyrazole Ring

  摘要：

  Thirteen novel ( E)- R-( methoxyimino) benzeneacetate derivatives, the analogues of strobilurins, which contain two pharmacophoric substructures of the methyl ( E)- methoxyiminoacetate moiety and 1,3,5-substituted pyrazole ring, were stereoselectively synthesized. It was found that the coupling reaction could give stereoselectively ( E: Z ca. 14: 1) the key intermediate material ( E)- methyl 2-( hydroxyimino)2- o- tolyl acetate ( 2). An X- ray crystallographic structure determination was carried out in a representative product. The preliminary bioassays indicated that all of the compounds 1 showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola, and Bipolaris mayclis.

  DOI：

  10.1021/jf060074f

文献信息

• Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives
  作者：Hong Dai、Linyu Ye、Huiyang Zhuang、Baojiang Dai、Yuan Fang、Yujun Shi

  DOI：10.3390/molecules201219811

  日期：——

  In this study, in order to find novel biologically active pyrazole oxime compounds, a number of dichloro-allyloxy-phenol-containing pyrazole oximes were designed and synthesized according to the method of active group combination. All of the target compounds were confirmed by 1H-NMR, 13C-NMR and elemental analysis. In addition, bioassays showed that all of the newly synthesized compounds had no acaricidal activity against Tetranychus cinnabarinus and low insecticidal activity against Aphis craccivora at tested concentrations. However, most of them displayed excellent insecticidal activity against Oriental armyworm at a concentration of 500 μg/mL, and some designed compounds still exhibited potent insecticidal activity against Oriental armyworm even at the dose of 20 μg/mL, especially compounds 7f, 7n and 7p had 100%, 90% and 90% inhibition rates, respectively, which were comparable to that of the control pyridalyl.

  在本研究中，为了寻找新型生物活性吡唑肟化合物，根据活性基团组合的方法设计并合成了多种含有二氯烯丙氧基苯酚的吡唑肟类化合物。所有目标化合物均通过1H-NMR、13C-NMR和元素分析得到确认。此外，生物测定显示，所有新合成的化合物对朱砂叶螨无杀螨活性，对豌豆蚜的杀虫活性较低（测试浓度下）。然而，它们大多数在500 μg/mL浓度下对东方粘虫显示出优异的杀虫活性，其中某些设计化合物甚至在20 μg/mL剂量下仍对东方粘虫表现出强效的杀虫活性，特别是化合物7f、7n和7p分别达到了100%、90%和90%的抑制率，这些结果与对照化合物pyridalyl相媲美。
• Synthesis and biological activities of novel 1,3,4-thiadiazole-containing pyrazole oxime derivatives
  作者：Hong Dai、Gang Li、Jia Chen、Yujun Shi、Shushan Ge、Chongguang Fan、Haibing He

  DOI：10.1016/j.bmcl.2016.04.094

  日期：2016.8

  4-thiadiazole-containing pyrazole oximes was designed and synthesized. Their acaricidal and insecticidal activities were evaluated. Bioassay results indicated that some target compounds exhibited good acaricidal and insecticidal properties. Especially, compound 8m had 80% acaricidal activity against Tetranychus cinnabarinus at the concentration of 50 μg/mL, compound 8f displayed 100% insecticidal activities against

  设计并合成了一个新的含1,3,4-噻二唑的吡唑肟库。他们的杀螨和杀虫活性进行了评估。生物测定结果表明，某些目标化合物具有良好的杀螨和杀虫特性。尤其是，化合物8m在浓度为50μg/ mL时对朱砂叶螨有80％的杀螨活性，化合物8f在浓度为50μg/ mL时对蟹蚜有100％的杀虫活性，化合物8r和8w对蚜虫有100％的杀虫活性。小菜蛾的浓度为50μg/ mL。此外，化合物8r（LC50  = 19.61微克/毫升）和8瓦特（LC 50  = 9.78微克/毫升）具有可比较的或甚至更好的杀虫活性比对照Pyridalyl（LC 50  = 17.40微克/毫升）对小菜蛾。