3,5-diphenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole | 1342639-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-diphenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole
• 英文别名: 3,5-Diphenyl-1-[4-(trifluoromethyl)phenyl]pyrazole
• CAS: 1342639-10-4
• 化学式: C₂₂H₁₅F₃N₂
• 分子量: 364.37
• InChiKey: WQEFRWRCCGXQBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-diphenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 1-(4-trifluoromethylphenyl)-3,4,5-triphenyl-1H-pyrazole
  参考文献：
  名称：

  AIEE phenomenon: tetraaryl vs. triaryl pyrazoles

  摘要：

  合成了一系列四芳基吡唑衍生物，并探索了AIEE现象。

  DOI：

  10.1039/c5cc05973a
• 作为产物：
  描述：

  (Z)-1-(1,3-diphenylprop-2-yn-1-ylidene)-2-(4-(trifluoromethyl)phenyl)hydrazine 在 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以88%的产率得到3,5-diphenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis of Pyrazoles via CuI-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones

  摘要：

  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.

  DOI：

  10.1021/jo201685p

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。
• Isolation and Characterization of Regioisomers of Pyrazole-Based Palladacycles and Their Use in α-Alkylation of Ketones Using Alcohols
  作者：Ramesh Mamidala、Shaikh Samser、Nishant Sharma、Upakarasamy Lourderaj、Krishnan Venkatasubbaiah

  DOI：10.1021/acs.organomet.7b00478

  日期：2017.9.11

  palladacycles (1 and 2) were synthesized by the aromatic C–H bond activation of N/3-aryl ring. The application of these regioisomers as catalysts to enable the formation of α-alkylated ketones or quinolines with alcohols using a hydrogen borrowing process is evaluated. Experimental results reveal that palladacycle 2 is superior over palladacycle 1 to catalyze the reaction under similar reaction conditions

  3,5-二苯基-1-（4-（三氟甲基）苯基）-1 H-吡唑基四氢呋喃环化合物（1和2）的区域异构体是通过N / 3-芳基环的芳族C–H键活化合成的。评估了这些区域异构体作为催化剂的应用，以使用氢借入过程与醇形成α-烷基化的酮或喹啉。实验结果表明，在相似的反应条件下，Palladacycle 2在催化反应方面优于Palladacycle 1。Palladacycles 1和2的反应机理使用密度泛函理论（DFT）方法研究了苯乙酮催化的α-烷基化反应。DFT研究表明，对于烷基化反应，Palladacycle 2具有比Palladacycle 1更低的能垒，这与在实验中看到的Palladacycle 2更好的催化活性是一致的。发现palladacycle-phosphine系统具有宽泛的官能团，可作为无溶剂条件下合成α-烷基化产物的有效方法。此外，合成方案已成功应用于从简单的起始原料制备多奈哌齐（一种用于治疗阿尔茨海默氏病的药物）。
• Copper-Catalyzed Aerobic C(sp²)–H Functionalization for C–N Bond Formation: Synthesis of Pyrazoles and Indazoles
  作者：Xianwei Li、Li He、Huoji Chen、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/jo400162d

  日期：2013.4.19

  A simple, practical, and highly efficient synthesis of pyrazoles and indazoles via copper-catalyzed direct aerobic oxidative C(sp2)–H amination has been reported herein. This process tolerated a variety of functional groups under mild conditions. Further diversification of pyrazoles was also investigated, which provided its potential for drug discovery.

  本文报道了通过铜催化的直接好氧氧化C（sp 2）-H胺的合成简单，实用，高效的吡唑和吲唑合成方法。在温和条件下，该过程可耐受各种官能团。还研究了吡唑的进一步多样化，这为其药物发现提供了潜力。
• Copper-catalyzed tandem cyclization/arylation of α,β-alkynic hydrazones with diaryliodonium salts: synthesis of <i>N</i>-arylpyrazoles
  作者：Sushanta Kumar Parida、Saurav Joshi、Sandip Murarka

  DOI：10.1039/d3ob00899a

  日期：——

  A copper-catalyzed efficient method for the synthesis of a diverse variety of substituted N-aryl pyrazoles from readily available α,β-alkynic N-tosyl hydrazones and diaryliodonium triflates is realized. This one-pot multi-step methodology features a broad scope with good yields, scalability, and appreciable functional group tolerance. Detailed control experiments reveal that the reaction proceeds through

  实现了一种铜催化的有效方法，用于从容易获得的α,β-炔基N-甲苯磺酰腙和三氟甲磺酸二芳基碘鎓合成多种取代的N-芳基吡唑。这种一锅多步骤方法具有广泛的范围、良好的产量、​​可扩展性和可观的官能团耐受性。详细的控制实验表明，反应通过串联环化/脱保护/芳基化事件进行，其中铜催化剂发挥着独特的作用。
• AIEE phenomenon: tetraaryl vs. triaryl pyrazoles
  作者：Sayani Mukherjee、P. S. Salini、A. Srinivasan、S. Peruncheralathan

  DOI：10.1039/c5cc05973a

  日期：——

  A library of tetraaryl pyrazole derivatives were synthesized and the AIEE phenomenon was explored.

  合成了一系列四芳基吡唑衍生物，并探索了AIEE现象。