3-(2-甲氧基苯基)-1,5-二苯基-1H-吡唑 | 1426534-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(2-甲氧基苯基)-1,5-二苯基-1H-吡唑
• 英文名称: 3-(2-methoxyphenyl)-1,5-diphenyl-1H-pyrazole
• 英文别名: 3-(2-Methoxyphenyl)-1,5-diphenylpyrazole；3-(2-methoxyphenyl)-1,5-diphenylpyrazole
• CAS: 1426534-15-7
• 化学式: C₂₂H₁₈N₂O
• 分子量: 326.398
• InChiKey: BZPZHUTZDYVCLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-甲氧基苯基)-1,5-二苯基-1H-吡唑 在 吡啶 、 palladium diacetate 、 三溴化硼 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 2-(2'-(1,5-diphenyl-1H-pyrazol-3-yl)biphenyl-3-yloxy)acetate acid
  参考文献：
  名称：

  Structure-guided design, synthesis and in vitro evaluation of a series of pyrazole-based fatty acid binding protein (FABP) 3 ligands

  摘要：

  We designed a series of pyrazole-based carboxylic acids as candidate ligands of heart fatty acid binding protein (H-FABP, or FABP3), based on a comparison of the X-ray crystallographic structures of adipocyte fatty acid binding protein (FABP4)-selective inhibitor (BMS309403) complex and FABP3-elaidic acid complex. Some of the synthesized compounds exhibited dual FABP3/4 ligand activity, and some exhibited selectivity for FABP3. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.054
• 作为产物：
  描述：

  2'-甲氧基苯乙酮 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 乙醇 、 苯 为溶剂， 反应 84.0h， 生成 3-(2-甲氧基苯基)-1,5-二苯基-1H-吡唑
  参考文献：
  名称：

  Structure-guided design, synthesis and in vitro evaluation of a series of pyrazole-based fatty acid binding protein (FABP) 3 ligands

  摘要：

  We designed a series of pyrazole-based carboxylic acids as candidate ligands of heart fatty acid binding protein (H-FABP, or FABP3), based on a comparison of the X-ray crystallographic structures of adipocyte fatty acid binding protein (FABP4)-selective inhibitor (BMS309403) complex and FABP3-elaidic acid complex. Some of the synthesized compounds exhibited dual FABP3/4 ligand activity, and some exhibited selectivity for FABP3. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.054

文献信息

• A Regioselective Approach to Trisubstituted Pyrazoles via Palladium-Catalyzed Oxidative Sonogashira-Carbonylation of Arylhydrazines
  作者：Yongliang Tu、Zhenming Zhang、Tao Wang、Jiamei Ke、Junfeng Zhao

  DOI：10.1021/acs.orglett.7b01447

  日期：2017.7.7

  A palladium-catalyzed oxidative carbonylation of arylhydrazines and alkynes with balloon pressure CO/O2 to afford trisubstituted pyrazoles in a one-pot manner has been developed. The formation of trisubstituted pyrazoles involves a sequential C–N bond cleavage, carbonylation, Sonogashira coupling, Michael addition, and intramolecular condensation cyclization tandem process. An unprecedented oxidative

  已经开发了用球罐压力CO / O 2进行钯催化的芳基肼和炔烃的氧化羰基化反应，以一锅法得到三取代的吡唑。三取代吡唑的形成涉及连续的C–N键断裂，羰基化，Sonogashira偶联，迈克尔加成和分子内缩合环化串联过程。芳基肼的空前的氧化Sonogashira-羰基化反应在如此简便的吡唑方法中起着关键作用。
• Photooxidation of 3,5-diaryl-1-phenyl-2-pyrazolines: Experimental and computational studies
  作者：Marzieh Soltani、Hamid Reza Memarian、Hassan Sabzyan

  DOI：10.1016/j.jphotochem.2019.112285

  日期：2020.2

  Photooxidation of various 2-pyrazolines is studied experimentally and computationally. Experimental results show that the electron-donating/withdrawing substituents increases/decreases the rate of this photoreaction. The proposed light-induced electron-transfer mechanism explains the steric and electronic effects of the substituents, co-planarity of the aryl rings substitutions, orientations of the

  实验和计算研究了各种2-吡唑啉的光氧化作用。实验结果表明，给电子/吸电子取代基增加/降低了这种光反应的速率。拟议的光诱导电子转移机理解释了取代基的空间和电子效应，芳基环取代基的共面性，C 3-芳基环向C 3 = N 2的方向双键与溶剂在照射时间上反应完全。计算（TD）B3LYP / 6-311 ++ G（d，p）结果，包括前沿轨道能量，UV-可见跃迁，静电势，CHELPG电荷，用于发现和描述隧道电子转移过程及其相关结构弛豫形成反应的速率决定步骤，并证明取代对反应速率的影响是正确的。第一次电子转移后形成的中间体络合物仅在其三重态下才进行质子转移步骤。2-吡唑啉的三重态激发态可能对电子转移步骤几乎没有贡献。循环伏安法测量结果支持了光化学结果。
• Synthesis, structural, and photophysical properties of pyrazolyl bis(pentafluorophenyl)boron complexes
  作者：Anna Chandrasekar Murali、Preeta Pratakshya、Pratiksha Patel、Prakash Nayak、Saravanan Peruncheralathan、Krishnan Venkatasubbaiah

  DOI：10.1039/d3nj03025c

  日期：——

  organoboron complexes have emerged as promising luminescent materials due to their enhanced stabilities, high electron affinities, and tuneable fluorescence properties. Herein, we report the synthesis, structure, and photophysical properties of two different types of N,O-chelated tetra-aryl pyrazole-based organoboron compounds. We also investigated the aggregation-induced enhanced emission properties of the

  发光材料由于其在光电子学、传感和医学诊断方面的潜在应用而引起了人们的广泛研究兴趣。在此背景下，四配位有机硼配合物由于其增强的稳定性、高电子亲和力和可调谐的荧光特性而成为有前途的发光材料。在此，我们报道了两种不同类型的N、O的合成、结构和光物理性质-螯合四芳基吡唑基有机硼化合物。我们还研究了合成复合物的聚集诱导增强发射特性，并进一步证明了它们在苦味酸传感中的实用性。这些化合物的吸收和发射行为表明，硼螯合位置在决定其光物理性质及其传感行为方面起着至关重要的作用。
• Mechanistic insights of the copper(<scp>i</scp>)-catalysed reaction between chlorohydrazones and terminal alkynes
  作者：Alessandro Ponti、Alessandra Silvani、Giorgio Molteni

  DOI：10.1039/d3nj02712k

  日期：——

  Deuterium incorporation in the 5-substituted pyrazoles arising from the copper(I)-catalysed reaction between chlorohydrazones and terminal acetylenes suggests the intermediacy of copper(I)-complexed alkynylhydrazones. Since the efficiency of such a complexation depends on both the chlorohydrazone and the solvent, the obtainment of the pyrazoles and/or the corresponding alkynylhydrazones is variable

  由铜( I )催化氯腙和末端乙炔之间的反应产生的5-取代吡唑中的氘掺入表明铜( I )络合的炔基腙的中间作用。由于这种络合的效率取决于氯代腙和溶剂，因此吡唑和/或相应的炔基腙的获得根据反应条件而变化。铜( I )络合的炔基腙中间体应该在所提出的催化循环中发挥关键作用。