5-(4-methoxyphenyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole | 1342638-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-methoxyphenyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole
• 英文别名: 5-(4-Methoxyphenyl)-1-[4-(trifluoromethyl)phenyl]pyrazole
• CAS: 1342638-89-4
• 化学式: C₁₇H₁₃F₃N₂O
• 分子量: 318.298
• InChiKey: WNFKUXRFJMNUGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-Trimethylsiloxy-1-(4-methoxyphenyl)cyclopropane 在 甲醇 、 tetrafluoroboric acid 、 三甲基氯硅烷 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 5-(4-methoxyphenyl)-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole
  参考文献：
  名称：

  Arenediazonium的光催化环加成物中的芳基吡唑。

  摘要：

  报道了由芳族二氮杂鎓和芳基环丙醇光催化合成1，5-二芳基吡唑。该反应在温和的条件下（室温，20分钟）与催化的[Ru（bpy）3 ] 2+在蓝光下进行，并显示出与多个官能团（例如I，SF 5，SO 2 NH 2，N 3）的相容性，CN）和完善的区域控制水平。机理研究（发光光谱，CV，DFT，自由基俘获，量子产率测定）证明了激发光催化剂的初始氧化猝灭和自由基链机理的运行。

  DOI：

  10.1021/acs.orglett.0c02514

文献信息

• Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles
  作者：J C JEYAVEERAN、CHANDRASEKAR PRAVEEN、Y ARUN、A A M PRINCE、P T PERUMAL

  DOI：10.1007/s12039-015-0993-9

  日期：2016.1

  The synthesis of substituted isoxazoles and pyrazoles through a general cycloisomerization methodology has been reported. The capability of gold(III) chloride to promote cycloisomerization of both α, β-acetylenic oximes and α, β-acetylenic hydrazones is the centrepiece of the strategy. A range of acetylenic precursors were investigated to afford 28 examples of the products with good to excellent chemical yields. Selected compounds were screened for their cytotoxic potential towards COLO320 cancer cell lines. The IC50 values of the tested compounds were in the micromolar range, with the best compound, 5-(6-Methoxy-naphthalen-2-yl)-3-phenyl-isoxazole (3h) displaying an IC50 of 38.9 μM. For this compound, the crystal structure in complex with Aurora-A kinase was obtained which revealed details of its binding mode within the active site with a free energy of binding -9.54 kcal/mol.

  通过一种通用的环异构化方法，已经报道了取代异恶唑和吡唑的合成。金(III)氯化物促进α,β-炔基肟和α,β-炔基脒的环异构化的能力是该策略的核心。研究了一系列炔基前体，以良好的至优秀的化学收率得到了28个产物实例。选定的化合物对COLO320癌细胞系的细胞毒性潜力进行了筛选。测试化合物的IC50值在微摩尔范围内，其中最佳化合物5-(6-甲氧基萘-2-基)-3-苯基异恶唑(3h)的IC50值为38.9 μM。对于该化合物，获得了与Aurora-A激酶复合的晶体结构，揭示了其在活性位点内的结合模式，结合自由能为-9.54 kcal/mol。
• Synthesis of Pyrazoles via CuI-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones
  作者：Metin Zora、Arif Kivrak

  DOI：10.1021/jo201685p

  日期：2011.11.18

  Synthesis of pyrazoles via electrophilic cyclization of alpha,beta-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, alpha,beta-alkynic hydrazones, prepared readily from hydrazines and propargyl aldehydes and ketones, undergo electrophilic cyclization to afford pyrazole derivatives in good to excellent yields. The reaction appears to be general for a variety of alpha,beta-alkynic hydrazones and tolerates the presence of aliphatic, aromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.