1-[(4-甲基苯基)甲基]-4-硝基-1H-吡唑 | 400877-60-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 1-[(4-甲基苯基)甲基]-4-硝基-1H-吡唑
• 英文名称: 1-[(4-methylphenyl)methyl]-4-nitro-1H-pyrazole
• 英文别名: 1-(4-methylbenzyl)-4-nitro-1H-pyrazole；1-(p-methylbenzyl)-4-nitropyrazole；1-[(4-methylphenyl)methyl]-4-nitropyrazole
• CAS: 400877-60-3
• 化学式: C₁₁H₁₁N₃O₂
• mdl: MFCD02029346
• 分子量: 217.227
• InChiKey: LWRGNXGRIFXGAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 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-[(4-甲基苯基)甲基]-4-硝基-1H-吡唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三甲基乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(4-methylbenzyl)-7,8-dimethoxy-1H-pyrazolo[4,3-c]isoquinoline
  参考文献：
  名称：

  Regioselective and Guided C–H Activation of 4-Nitropyrazoles

  摘要：

  A divergent and regioselective approach to 5-aryl-4-nitro-1H-pyrazoles was developed by guided transition-metal-catalyzed arylation of 4-nitro-1H-pyrazoles. This method provides a convenient tool for the functionalization of the pharmacologically relevant pyrazole scaffold. The scope and limitations of the methodology were studied.

  DOI：

  10.1021/jo4025418
• 作为产物：
  描述：

  4-硝基吡唑 、 4-甲基苄溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以87%的产率得到1-[(4-甲基苯基)甲基]-4-硝基-1H-吡唑
  参考文献：
  名称：

  Regioselective and Guided C–H Activation of 4-Nitropyrazoles

  摘要：

  A divergent and regioselective approach to 5-aryl-4-nitro-1H-pyrazoles was developed by guided transition-metal-catalyzed arylation of 4-nitro-1H-pyrazoles. This method provides a convenient tool for the functionalization of the pharmacologically relevant pyrazole scaffold. The scope and limitations of the methodology were studied.

  DOI：

  10.1021/jo4025418

文献信息

• Copper-catalyzed direct C–H arylselenation of 4-nitro-pyrazoles and other heterocycles with selenium powder and aryl iodides. Access to unsymmetrical heteroaryl selenides
  作者：Michał Jakubczyk、Satenik Mkrtchyan、Izabela D. Madura、Paulina H. Marek、Viktor O. Iaroshenko

  DOI：10.1039/c9ra05004c

  日期：——

  A one-pot, Cu-catalyzed direct C–H arylselenation protocol using elemental Se and aryl iodides was developed for nitro-substituted, N-alkylated pyrazoles, imidazoles and other heterocycles including 4H-chromen-4-one. This general and concise method allows one to obtain a large number of unsymmetrical heteroaryl selenides bearing a variety of substituents. The presence of the nitro group was confirmed

  针对硝基取代的N-烷基化吡唑、咪唑和包括 4 H -chromen-4-one 在内的其他杂环，开发了一种使用元素 Se 和芳基碘化物的一锅铜催化直接 C-H 芳基硒化方案。这种通用而简洁的方法允许获得大量带有多种取代基的不对称杂芳基硒化物。确认硝基的存在对于 C-H 活化至关重要，也可用于进一步的功能化和操作。还使用开发的合成方案合成了几个杂环化苯并硒嗪的例子。
• ——
  作者：V. A. Chauzov、V. Z. Parchinsky、E. V. Sinelshchikova、V. A. Petrosyan

  DOI：10.1023/a:1014023310543

  日期：——

  As exemplified for the first time by pyrazole and its 4-nitro and 3,5-dimethyl derivatives, N-arylation of pyrazoles can be performed under conditions of undivided-cell amperostatic electrolysis (Pt electrodes, MeCN) of systems containing the pyrazolate anion and (or) pyrazole, arene (benzene, 1,4-dimethoxybenzene, or xylene), and a supporting electrolyte. In the case of electrolysis involving 1,4-dimethoxybenzene as arene, N-arylation followed simultaneously three routes to form an ortho-substitution product (1,4-dimethoxy-2-(pyrazol-1-yl)benzene), an ipso-substitution product (4-methoxy-1-(pyrazol-1-yl)benzene), and all ipso-bisaddition product (1,4-dimethoxy-1,4-di(pyrazol-1-yl)cyclohexa-2,5-diene) in a total current yield of up to 50%. The acid-base properties of the pyrazoles under study affect the ratio of the N-arylation products and govern the required composition of the starting reaction mixture. In the case of a stronger base, such as 3,5-dimethylpyrazole, N-arylation with 1,4-dimethoxybenzene occurred even in the pyrazole-arene-tetraalkylammonium perchlorate system, whereas N-arylation of 4-nitropyrazole (a weaker base) proceeded only in the presence of the pyrazolate anion or another base, viz., sym-collidine, Oxidation of arene to the radical cation is the key anodic reaction. Not only the pyrazolate anion, but also highly basic pyrazole or a solvate complex of weakly basic pyrazole with collidine can serve as a nucleophilic partner in subsequent transformations of these radical cations.
• Palladium Catalyzed Arylation and Benzylation of Nitroarenes Using Aryl Sulfonates and Benzyl Acetates
  作者：Zubaoyi Yi、Yodit Aschenaki、Ryan Daley、Stephen Davick、Abigail Schnaith、Rylee Wander、Dipannita Kalyani

  DOI：10.1021/acs.joc.7b00550

  日期：2017.7.7

  Pd-catalyzed arylation or benzylation of nitroazoles using aryl sulfonates or benzyl acetates is described. Electronically varied aryl tosylates and mesylates, as well as benzyl acetates, afford the arylated and benzylated products. Arylation of nitrobenzene is also reported. The relative rate for the arylation of halides is greater than that of tosylates using the reported reaction parameters. These studies enhance the scope of electrophiles for nitroarene arylations and benzylations, which was hitherto limited to the use of halide electrophiles.
• Glycopeptide Antibiotic Monomer Derivatives
  申请人：Arimoto Hirokazu

  公开号：US20080097078A1

  公开（公告）日：2008-04-24

  Novel glycopeptide antibiotic derivatives. These derivatives are represented by the formula (aglycon part of glycopeptide antibiotic derivative)-(Sac-NH)—R A [wherein (aglycon part of glycopeptide antibiotic derivative) is the part formed by removing the sugar part from a known glycopeptide antibiotic derivative; (Sac-NH) part is an amino sugar part or a sugar chain part containing an amino sugar; and R A represents, e.g., the formula —X 1 —Ar 1 —X 2 —Y—X 3 —Ar 2 (wherein X 1 , X 2 , and X 3 each represents 1) a single bond or 2) a heteroatom or heteroatom-containing group selected from the group consisting of —N═, ═N—, —NR 1 —, —O—, etc.; Y represents —NR 2 CO— or —CONR 2 — (wherein R 2 represents hydrogen or lower alkyl), etc.)]. These derivatives have antibacterial activity against vancomycin-resistant bacteria.
• US8778874B2
  申请人：——

  公开号：US8778874B2

  公开（公告）日：2014-07-15