2-(1H-pyrazol-1-yl)pyrazine | 123464-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(1H-pyrazol-1-yl)pyrazine
• 英文别名: 2-Pyrazinyl pyrazole；2-pyrazol-1-ylpyrazine
• CAS: 123464-67-5
• 化学式: C₇H₆N₄
• 分子量: 146.151
• InChiKey: MFMYKRDGTJWLIY-UHFFFAOYSA-N

物化性质

• 沸点：
  278.7±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-pyrazol-1-yl)pyrazine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 溴 、 potassium acetate 、 caesium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-(1-methylpiperidin-4-yl)-3-[1-(pyrazin-2-yI)-1H-pyrazol-4-yl]imidazo[1,2-b]pyridazin-6-amine
  参考文献：
  名称：

  Imidazopyridazines as potent inhibitors of Plasmodium falciparum calcium-dependent protein kinase 1 (PfCDPK1): Preparation and evaluation of pyrazole linked analogues

  摘要：

  The structural diversity and SAR in a series of imidazopyridazine inhibitors of Plasmodium falciparum calcium dependent protein kinase 1 (PfCDPK1) has been explored and extended. The opportunity to further improve key ADME parameters by means of lowering log D was identified, and this was achieved by replacement of a six-membered (hetero)aromatic linker with a pyrazole. A short SAR study has delivered key examples with useful in vitro activity and ADME profiles, good selectivity against a human kinase panel and improved levels of lipophilic ligand efficiency. These new analogues thus provide a credible additional route to further development of the series. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.010
• 作为产物：
  描述：

  吡唑 、 2-氯吡嗪 在 potassium tert-butylate 、 C₅₁H₄₀BrCuN₃OP₂⁽¹⁺⁾*F₆P^(1-) 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以94%的产率得到2-(1H-pyrazol-1-yl)pyrazine
  参考文献：
  名称：

  四配位Cu(I)-N-杂环卡宾配合物：合成、结构、性质和氨基化在合成1-(2-N-杂芳基)-1H-吡唑中的应用

  摘要：

  成功制备并表征了一种新型的发光、阳离子、杂配、四配位 Cu(I)-N-杂环卡宾配合物 [Cu(Br-Pyim)(POP)](PF6)，其中 Br-Pyim 和 POP 为 1- (6-bromopyridin-2-yl)imidazole-3-benzyl-2-ylidene 和双[2-(二苯基膦)苯基]醚，分别。其详细结构由单晶 X 射线分析确定。它在室温下以结晶粉末形式存在，并呈现出明亮的黄绿色发光。还研究了使用 Cu(I)-N-杂环卡宾配合物作为胺化反应的催化剂，发现对于 2-N-杂芳基氯化物与吡唑的胺化非常有效，得到所需的取代 1-( 2-N-杂芳基)-1H-吡唑的产率良好。

  DOI：

  10.1177/1747519820921819

文献信息

• A four-coordinate Cu(I)–<i>N</i>-heterocyclic carbene complex: Synthesis, structure, properties, and application in amination for the synthesis of 1-(2-<i>N</i>-heteroaryl)-1<i>H</i>-pyrazoles
  作者：Chen Xu、Hong-Mei Li、Zhi-Qiang Wang、Wei-Jun Fu

  DOI：10.1177/1747519820921819

  日期：2020.11

  A new luminescent, cationic, heteroleptic, four-coordinate Cu(I)–N-heterocyclic carbene complex [Cu(Br-Pyim)(POP)](PF6) is successfully prepared and characterized, where Br-Pyim and POP are 1-(6-bromopyridin-2-yl)imidazole-3-benzyl-2-ylidene and bis[2-(diphenylphosphino)phenyl]ether, respectively. Its detailed structure is determined by single-crystal X-ray analysis. It exists as a crystalline powder

  成功制备并表征了一种新型的发光、阳离子、杂配、四配位 Cu(I)-N-杂环卡宾配合物 [Cu(Br-Pyim)(POP)](PF6)，其中 Br-Pyim 和 POP 为 1- (6-bromopyridin-2-yl)imidazole-3-benzyl-2-ylidene 和双[2-(二苯基膦)苯基]醚，分别。其详细结构由单晶 X 射线分析确定。它在室温下以结晶粉末形式存在，并呈现出明亮的黄绿色发光。还研究了使用 Cu(I)-N-杂环卡宾配合物作为胺化反应的催化剂，发现对于 2-N-杂芳基氯化物与吡唑的胺化非常有效，得到所需的取代 1-( 2-N-杂芳基)-1H-吡唑的产率良好。
• Direct, Metal-Free Amination of Heterocyclic Amides/Ureas with NH-Heterocycles and N-Substituted Anilines in POCl₃
  作者：Xiaohu Deng、Armin Roessler、Ivana Brdar、Roger Faessler、Jiejun Wu、Zachary S. Sales、Neelakandha S. Mani

  DOI：10.1021/jo201425q

  日期：2011.10.21

  A POCl3-mediated, direct amination reaction of heterocyclic amides/ureas with NH-heterocycles or N-substituted anilines is described. Compared to the existing methods, this operationally simple protocol provides unique reactivity and functional group compatibility because of the metal-free, acidic reaction conditions. The yields are generally excellent.

  描述了POCl 3介导的杂环酰胺/脲与NH-杂环或N-取代的苯胺的直接胺化反应。与现有方法相比，该操作简单的协议由于无金属的酸性反应条件，提供了独特的反应性和官能团兼容性。产量通常是极好的。
• Iron complex-catalyzed N-arylation of pyrazoles under aqueous medium
  作者：Hang Wai Lee、Albert S.C. Chan、Fuk Yee Kwong

  DOI：10.1016/j.tetlet.2009.08.018

  日期：2009.10

  diamine ligand is a highly effective catalyst for N-arylation of pyrazoles using aryl and heteroaryl iodides. It is notable to show that this complex is tolerable under aqueous medium and particularly the whole reaction utilizes water as the sole solvent without any additional organic co-solvents and surfactants. Attempted study using other nitrogen nucleophiles is described. This newly developed system provides

  具有构象刚性二胺配体的市售FeCl 3 ·6H 2 O是使用芳基和杂芳基碘化物使吡唑进行N-芳基化的高效催化剂。值得注意的是，表明该络合物在水性介质中是可耐受的，特别是整个反应利用水作为唯一的溶剂，而没有任何其他的有机助溶剂和表面活性剂。描述了尝试使用其他氮亲核试剂的研究。这个新开发的系统提供了Cu和Pd催化的N-芳基化反应的替代方案。
• Synthesis, spectroscopy, and electrochemistry of homo- and hetero-leptic ruthenium(II) complexes of new pyrazole-containing bidentate ligands
  作者：Peter J. Steel、Edwin C. Constable

  DOI：10.1039/dt9900001389

  日期：——

  and homoleptic [Ru(L–L′)3]2+ complexes, where bipy = 2,2′-bipyridine and L–L′ is one of nine new pyrazole-containing bidentate ligands, have been prepared. Full assignments have been made for the 1H and 13C n.m.r. spectra of the complexes in CD3CN and the origins of the co-ordination-induced shifts are discussed. The absorption spectra and redox properties of the complexes are also discussed.

  杂合[Ru（bipy）2（L–L'）] 2+和纯合[Ru（L–L'）3 ] 2+复合物，其中bipy = 2,2'-联吡啶，L–L'是九种之一制备了新的含吡唑的双齿配体。已对CD 3 CN中配合物的1 H和13 C nmr光谱进行了完全分配，并讨论了配位诱导的位移的起源。还讨论了配合物的吸收光谱和氧化还原性质。
• ECTOPARASITICIDAL ACTIVE SUBSTANCE COMBINATIONS
  申请人：Turberg Andreas

  公开号：US20140179623A1

  公开（公告）日：2014-06-26

  The present application relates to active compound combinations of pyrazin-2-ylpyrazoles (component A) with at least one further ectoparasiticide or synergists (component B), and to products comprising such active compound combinations. These active compound combinations are suitable for controlling animal pests in the field of veterinary medicine.

  本申请涉及吡嗪-2-基吡唑（A组分）与至少一种其他外寄生虫药或增效剂（B组分）的活性化合物组合，以及包含这种活性化合物组合的产品。这些活性化合物组合适用于在兽医药学领域控制动物害虫。