1-[4-(1H-pyrazol-1-yl)phenyl]-1H-pyrazole | 67673-42-1

• 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-[4-(1H-pyrazol-1-yl)phenyl]-1H-pyrazole
• 英文别名: 1,1'-(1,4-phenylene)bis(1H-pyrazole)；1H,1'H-1,1'-p-phenylenebis(pyrazole)；1,4-di(1H-pyrazol-1-yl)benzene；1,4-Di(1-pyrazolyl)benzol；1H,1'H-1,1'-p-phenylene-bis-pyrazole；1H,1'H-1,1'-p-phenylene-bis-pyrazole；1,4-Bis(4'-pyrazolyl)benzene；1-(4-pyrazol-1-ylphenyl)pyrazole
• CAS: 67673-42-1
• 化学式: C₁₂H₁₀N₄
• 分子量: 210.238
• InChiKey: LCZAVAIUEZEXTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(1H-pyrazol-1-yl)phenyl]-1H-pyrazole 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 C₁₂H₈Li₂N₄
  参考文献：
  名称：

  Lexy, Herbert; Kauffmann, Thomas, Chemische Berichte, 1980, vol. 113, # 8, p. 2749 - 2754

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二溴苯 在 copper(I) oxide caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 120.0h， 生成 1-[4-(1H-pyrazol-1-yl)phenyl]-1H-pyrazole
  参考文献：
  名称：

  铜催化的吡唑 N-芳基化反应的温和条件

  摘要：

  铜催化吡唑与芳基或杂芳基溴化物或碘化物（可包括功能性取代基）的 N-芳基化反应是在迄今描述的最温和条件下进行的，通过将氧化亚铜与一套廉价的螯合肟型配体，此前未知可促进此类反应。提供氮和/或氧作为螯合原子的其他原始双齿、三齿或四齿配体也在此类芳基化中成功测试。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300709

文献信息

• N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides
  作者：Floris Chevallier、Yury S. Halauko、Christelle Pecceu、Ibrahim F. Nassar、To Uyen Dam、Thierry Roisnel、Vadim E. Matulis、Oleg A. Ivashkevich、Florence Mongin

  DOI：10.1039/c1ob05267e

  日期：——

  A series of N-aryl and N-heteroaryl pyrazoles have been deproto-metallated using a 2,2,6,6-tetramethylpiperidino-based mixed lithium–zinc combination. Mono-, di-, and tri-iodides have been obtained after subsequent trapping with iodine, depending on the substrate and on the quantity of base used. The results have been discussed in the light of the CH acidities of the substrates, determined both in the gas phase and in THF solution using the DFT B3LYP method.

  一系列N-芳基和N-杂芳基吡唑化合物通过基于2,2,6,6-四甲基哌啶的混合锂-锌试剂进行了去质子金属化反应。在随后与碘的捕获反应中，根据底物和所用碱的量的不同，分别得到了单碘、二碘和三碘化合物。研究结果根据底物的CH酸性进行了讨论，这些酸性在气相和THF溶液中均通过DFT B3LYP方法进行了测定。
• <scp>l</scp><i>-</i>(<i>−</i>)<i>-</i>Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles
  作者：Qifan Zhou、Fangyu Du、Yuanguang Chen、Yang Fu、Wenjiao Sun、Ying Wu、Guoliang Chen

  DOI：10.1021/acs.joc.9b00997

  日期：2019.6.21

  l-(−)-Quebrachitol (QCT) has been found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.

  已经发现1 -（-）-木糖醇（QCT）作为铜粉的配体，用于含氮杂环与芳基卤化物的选择性N-芳基化。此外，另一种潜在的催化体系（铜粉/ QCT / t- BuOK）已成功地用于未活化的芳基氯化物。
• Method of forming a carbon-carbon or carbon-heteroatom linkage
  申请人：Taillefer Marc

  公开号：US20050234239A1

  公开（公告）日：2005-10-20

  The invention relates to a method of creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound. More specifically, the invention relates to the creation of a carbon-nitrogen linkage involving the arylation of nitrogenous organic derivatives. The inventive method consists in creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound providing a carbon atom or a heteroatom (HE) capable of being substituted for the leaving group, thereby creating a C—C or C-HE linkage. The invention is characterised in that the reaction is carried out in the presence of an effective quantity of a catalyst based on copper and at least one ligand comprising at least one imine function and at least one additional nitrogen atom as chelating atoms

  该发明涉及一种通过使带有离去基团和亲核化合物的不饱和化合物发生反应来创建碳-碳或碳-杂原子键的方法。更具体地，该发明涉及涉及通过芳基化氮有机衍生物来创建碳-氮键。该创新方法包括通过使带有离去基团和提供能够替代离去基团的碳原子或杂原子（HE）的亲核化合物发生反应来创建碳-碳或碳-杂原子键。该发明的特点在于，在铜基催化剂和至少包含至少一个亚胺功能和至少一个额外氮原子作为螯合原子的配体的有效量存在下进行反应。
• Process for arylating or vinylating or alkynating a nucleophilic compound
  申请人：——

  公开号：US20030236413A1

  公开（公告）日：2003-12-25

  The present invention concerns a process for arylating or vinylating or alkynating a nucleophilic compound. More particularly, the invention concerns arylating nitrogen-containing organic derivatives. The arylating or vinylating or alkynating process of the invention consists of reacting a nucleophilic compound with a compound carrying a leaving group and is characterized in that the reaction is carried out in the presence of an effective quantity of a catalyst based on a metallic element M selected from groups (VIII), (Ib) and (IIb) of the periodic table and at least one ligand comprising at least one imine function and at least one supplemental nitrogen atom as the chelating atoms.

  本发明涉及一种用于芳基化、乙烯基化或炔基化亲核化合物的过程。更具体地，本发明涉及芳基化含氮有机衍生物的过程。本发明中的芳基化、乙烯基化或炔基化过程包括将亲核化合物与携带一个离去基团的化合物反应，其特点在于在金属元素M基的催化剂的有效量存在下进行反应，金属元素M选自周期表中的(VIII)、(Ib)和(IIb)族，并且至少包括一个含有至少一个亚胺功能和至少一个补充氮原子作为螯合原子的配体。
• Electrophilic iodination: a gateway to high iodine compounds and energetic materials
  作者：Deepak Chand、Chunlin He、Lauren A. Mitchell、Damon A. Parrish、Jean'ne M. Shreeve

  DOI：10.1039/c6dt02438f

  日期：——

  A large number of iodine atoms can be introduced into a single molecule in a one-pot reaction using trifluoroperacetic acid-mediated electrophilic iodination methodology. The scope of this reaction was investigated extensively using several pyrazole substrates which resulted in nine polyiodo pyrazole compounds with iodine content as high as 80%. This synthetic methodology was also utilized successfully

  使用三氟过氧乙酸介导的亲电子碘化方法，可以在一锅反应中将大量碘原子引入单个分子中。使用几种吡唑底物广泛研究了该反应的范围，得到了9种碘含量高达80％的多碘吡唑化合物。该合成方法也成功地用于苯并咪唑的碘化。将四碘代苯并咪唑用100％硝酸硝化，以高产率得到4,5,6,7-四硝基-1 H-苯并咪唑-2（3 H）-一（14）。所有这些材料都完全表征和化合物5，9，10和14用单晶X射线分析进一步证实。高密度，正氧平衡和非常好的冲击敏感度值表征14。首次将两个1,2,5-恶二唑-N-氧化物环引入苯并咪唑环（11），这显着提高了恶二唑-N-氧化物化合物的稳定性。