1-(1,1-dimethylethyl)-3-phenyl-1H-pyrazole-5-carboxylic acid | 1243251-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(1,1-dimethylethyl)-3-phenyl-1H-pyrazole-5-carboxylic acid
• 英文别名: 2-Tert-butyl-5-phenylpyrazole-3-carboxylic acid
• CAS: 1243251-76-4
• 化学式: C₁₄H₁₆N₂O₂
• 分子量: 244.293
• InChiKey: YWESBDYDBOKYAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1,1-dimethylethyl)-3-phenyl-1H-pyrazole-5-carboxylic acid 在 氯化亚砜 作用下， 反应 8.0h， 生成
  参考文献：
  名称：

  New Analogues of (E)-β-Farnesene with Insecticidal Activity and Binding Affinity to Aphid Odorant-Binding Proteins

  摘要：

  (E)-β-НАРСЕС is a strong and efficient ALARM PHENOMONE in most aphid species. However, its applications in agriculture are hindered by its relatively high VOLATILITY, susceptibility to OXIDATION, and complex and costly SYNTHESIS. In an effort to develop novel chemical entities for aphid CONTROL, we have designed and synthesized ANALOGUES of (E)-β-НАРСЕС, each bearing a PYRAZOLE moiety, a structural feature commonly found in several INSECTICIDES. Their structural analyses have been confirmed via (1)H NMR, ELEMENTAL ANALYSIS, HIGH-RESOLUTION MASS SPECTROSCOPY, and INFRARED SPECTROSCOPY. Binding activities to three ODDOR glVertex proteins (OBVs) of the pea aphid Acythosiphon pisum have been evaluated and correlative with the compounds' structures as a reference to (E)-β-НАРСЕС. Several derivatives were found to bind to A. pisum OBDs with a specificity comparable to that of (E)-β-НАРСЕС and exhibited ENTICING activity akin to that of thiacloprid, a widely used COMMERCIAL INSECTICIDE. The compounds synthesized in this study represent novel POTENTIAL AGENTS for POPULATION CONTROL of aphids and offer guidance for the design of ANALOGS of (E)-β-НАРСЕES endowed with both INSECTICIDAL and repellent properties for aphids.

  DOI：

  10.1021/jf104712c
• 作为产物：
  描述：

  3-phenyl-1-(1,1-dimethylethyl)-1H-pyrazole-5-carboxylate ethyl 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以94%的产率得到1-(1,1-dimethylethyl)-3-phenyl-1H-pyrazole-5-carboxylic acid
  参考文献：
  名称：

  通过截留反应形成[2]轮烷的过程中，供体和受体氢键之间的竞争竞争

  摘要：

  据报道，以1,2-双（氨基羰基- （1'-叔丁基-1 H-吡唑-[3'] 5'-基））-乙烷为模板合成苄基酰胺[2]轮烷。这些模板配备了基于叔丁基吡唑的塞子，并具有供体（NH）和受体（CO）的氢键基团。已显示[2]轮烷的合成高度依赖叔叔丁基吡唑瓶塞。虽然以1'，3'-二取代的吡唑为塞子单元的线被证明是合成[2]轮烷的极好模板，但是以1'，5'-二取代的吡唑为塞子单元的线并没有得到预期的结果。 [2]轮烷。使用NMR实验和X射线衍射对合成的[2]轮烷的结构进行了表征，后者表明大环化合物具有扭曲的椅构象。对分离的线的X射线结构和浓度依赖性NMR实验的深入研究似乎可以解释轮烷的形成对线的吡唑塞的取代方式的依赖性。

  DOI：

  10.1039/c7nj02443f