1-(2-甲基-2-丙基)-3-丙基-1H-吡唑-5-羧酸 | 1020724-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(2-甲基-2-丙基)-3-丙基-1H-吡唑-5-羧酸
• 英文名称: 1-(1,1-dimethylethyl)-3-propyl-1H-pyrazole-5-carboxylic acid
• 英文别名: 1-(tert-Butyl)-3-propyl-1H-pyrazole-5-carboxylic acid；2-tert-butyl-5-propylpyrazole-3-carboxylic acid
• CAS: 1020724-17-7
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: XRSZLEYQODSYAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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-(2-甲基-2-丙基)-3-丙基-1H-吡唑-5-羧酸 在 吡啶 、 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 [(2E)-3,7-dimethylocta-2,6-dienyl] 2-tert-butyl-5-propylpyrazole-3-carboxylate
  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：

  2-戊酮 在 乙醇 、 sodium 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 1-(2-甲基-2-丙基)-3-丙基-1H-吡唑-5-羧酸
  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

文献信息

• Competition between the donor and acceptor hydrogen bonds of the threads in the formation of [2]rotaxanes by clipping reaction
  作者：Marcos A. P. Martins、Geórgia C. Zimmer、Leticia V. Rodrigues、Tainára Orlando、Lilian Buriol、Mateo Alajarin、Jose Berna、Clarissa P. Frizzo、Helio G. Bonacorso、Nilo Zanatta

  DOI：10.1039/c7nj02443f

  日期：——

  excellent template for the synthesis of [2]rotaxanes, the thread with 1′,5′-disubstituted pyrazoles as stopper units did not yield the expected [2]rotaxane. The structure of the synthesized [2]rotaxanes was characterized using NMR experiments and X-ray diffraction, with the latter showing that the macrocycle adopts a distorted chair conformation. An in-depth study of the isolated thread's X-ray structures and

  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。