1-methyl-4-(4-nitrophenyl)-1H-pyrazole | 37921-15-6

• 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-methyl-4-(4-nitrophenyl)-1H-pyrazole
• 英文别名: 1-methyl-4-(4-nitrophenyl)pyrazole
• CAS: 37921-15-6
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: JQFBCQJJXJUQMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-4-(4-nitrophenyl)-1H-pyrazole 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以94%的产率得到4-(1-甲基-1H-吡唑-4-基)苯胺
  参考文献：
  名称：

  [EN] COMPOUNDS AND COMPOSITIONS AS MODULATORS OF TLR SIGNALING
  [FR] COMPOSÉS ET COMPOSITIONS UTILISÉS EN TANT QUE MODULATEURS DE LA SIGNALISATION TLR

  摘要：

  本发明公开涉及化合物、包含此类化合物的药物组合物，以及此类化合物在治疗炎症性疾病和与炎症信号传导过程相关的某些神经障碍的方法或药物中的用途，所述神经障碍包括但不限于错误折叠的蛋白质。

  公开号：

  WO2020198368A1
• 作为产物：
  描述：

  1-甲基-4-碘-吡唑 、 4-硝基苯基硼酸 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 0.08h， 以95%的产率得到1-methyl-4-(4-nitrophenyl)-1H-pyrazole
  参考文献：
  名称：

  Efficient synthesis of 4-substituted pyrazole via microwave-promoted Suzuki cross-coupling reaction

  摘要：

  Pyrazoles and their derivatives are important heterocycles found in nature and present in numerous bioactive compounds. In contrast to 3 or 5-aryl pyrazole, the preparation of 4-aryl pyrazole is fairly rare. Utilizing microwave irradiation, the synthesis of 4-substituted-arylpyrazole via Suzuki cross-coupling has been developed with a wide range of substrates. The remarkable advantages of this method are mild reaction conditions, simple operation, high yield, and short reaction time. Product structures were identified by MS, H-1 NMR, C-13 NMR, and elemental analysis. (C) 2014 Qiong-You Wu and Guang-Fu Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.03.013

文献信息

• [EN] CYCLIN-DEPENDENT KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES CYCLINE-DÉPENDANTES
  申请人：SPV THERAPEUTICS INC

  公开号：WO2020140055A1

  公开（公告）日：2020-07-02

  Described herein are compounds and their pharmaceutically acceptable salts, pharmaceutical compositions thereof, methods of treatment, and medical uses. The compounds described herein are modulators of cyclin-dependent kinases, and are useful in the treatment or alleviation of protein kinase associated disorders, including cancer, infectious diseases, autoimmune diseases, or cardiovascular diseases.

  本文描述了化合物及其药用盐，以及它们的药物组合物，治疗方法和医疗用途。本文描述的化合物是细胞周期依赖性激酶的调节剂，并且在治疗或缓解蛋白激酶相关疾病方面具有用途，包括癌症，传染病，自身免疫疾病或心血管疾病。
• [EN] CYCLIN-DEPENDENT KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES DÉPENDANTES DES CYCLINES
  申请人：SPV THERAPEUTICS INC

  公开号：WO2020140053A1

  公开（公告）日：2020-07-02

  Described herein are compounds and their pharmaceutically acceptable salts, pharmaceutical compositions thereof, methods of treatment, and medical uses. The compounds described herein are modulators of cyclin-dependent kinases, and are useful in the treatment or alleviation of protein kinase associated disorders, including cancer, infectious diseases, autoimmune diseases, or cardiovascular diseases.

  本文描述了化合物及其药用可接受的盐、药物组合物、治疗方法和医疗用途。本文描述的化合物是细胞周期依赖性激酶的调节剂，可用于治疗或缓解与蛋白激酶相关的疾病，包括癌症、传染病、自身免疫疾病或心血管疾病。
• Rhodium-Catalyzed Denitrogenative Diazole–Triazole Coupling toward Aza-Bridged Structures and Imidazole-Based Chelating Ligands
  作者：Julia O. Strelnikova、Alexander N. Koronatov、Nikolai V. Rostovskii、Alexander F. Khlebnikov、Olesya V. Khoroshilova、Mariya A. Kryukova、Mikhail S. Novikov

  DOI：10.1021/acs.orglett.1c01092

  日期：2021.6.4

  Rh2(Piv)4-catalyzed denitrogenative coupling of pyrazoles with 1-sulfonyl-1,2,3-triazoles, smoothly form 2,6,8-triazabicyclo[3.2.1]octa-3,6-dienes via intramolecular aza-Diels–Alder cycloaddition. This domino reaction, combined with the subsequent thermal or acid-catalyzed rearrangement of the cycloadducts, provides direct and flexible access to N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles.

  1,4,8-Triazaocta-1,3,5,7-tetraenes，由 Rh 2 (Piv) 4催化的吡唑与 1-磺酰基-1,2,3-三唑的脱氮偶联原位生成，顺利形成 2 ,6,8-三氮杂双环[3.2.1]octa-3,6-二烯通过分子内氮杂-Diels-Alder环加成反应。这种多米诺反应与随后的环加合物的热或酸催化重排相结合，提供了直接和灵活地获得N-磺酰化 ( Z )-2-(2-氨基乙烯基)咪唑的途径。
• Rh(II)-Catalyzed Ring Expansion of Pyrazoles with Diazocarbonyl Compounds as a Method for the Preparation of 1,2-Dihydropyrimidines
  作者：Alexander N. Koronatov、Nikolai V. Rostovskii、Alexander F. Khlebnikov、Mikhail S. Novikov

  DOI：10.1021/acs.joc.8b01228

  日期：2018.8.17

  A high yield synthesis of 1,2-dihydropyrimidines by the Rh(II)-catalyzed reaction of diazocarbonyl compounds with 1,4-di- and 1,4,5-trisubstituted pyrazoles is reported. This reaction represents the first example of a carbenoid insertion into a N–N bond and provides a novel approach to 4-unsubstituted 1,2-dihydropyrimidines with a broad range of functional group tolerance. According to DFT calculations

  报道了通过Rh（II）催化的重氮羰基化合物与1,4-二-和1,4,5-三取代的吡唑的高产率合成1,2-二氢嘧啶。该反应代表类胡萝卜素插入N–N键的第一个例子，它为具有范围广泛的官能团耐受性的4-未取代的1,2-二氢嘧啶提供了一种新颖的方法。根据DFT计算，吡唑环的扩环是通过依次形成与金属结合的吡唑鎓叶立德，无金属吡唑鎓叶立德和1,5-二氮杂己三烯并随后进行1,6-环化而进行的。
• Palladium-catalysed direct diarylations of pyrazoles with aryl bromides: a one step access to 4,5-diarylpyrazoles
  作者：Abdelilah Takfaoui、Liqin Zhao、Rachid Touzani、Pierre H. Dixneuf、Henri Doucet

  DOI：10.1016/j.tetlet.2014.01.079

  日期：2014.3

  The palladium-catalysed direct arylation of pyrazoles with aryl halides, using PdCl(C3H5)(dppb)/KOAc catalyst, reveals a similar reactivity of C4 and C5 CH bonds of pyrazoles, whereas the C3 CH bond is almost unreactive, and gives access in one step to a variety of 4,5-diarylpyrazoles. This CH bond functionalisation reaction tolerates a variety of substituents on the aryl bromide such as nitro, cyano

  使用PdCl（C 3 H 5）（dppb）/ KOAc催化剂，钯催化吡唑与芳基卤化物的直接芳基化反应显示出吡唑的C4和C5 C H键具有相似的反应性，而C3 C H键几乎不具有反应性，并一步一步即可获得各种4,5-二芳基吡唑类化合物。该C H键官能化反应容许芳基溴化物上的各种取代基，例如硝基，氰基，甲酰基，丙酰基，酯，氯，氟或三氟甲基。