1-丁基-4-硝基-1H-吡唑 | 1240574-64-4

• 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-丁基-4-硝基-1H-吡唑
• 英文名称: 1-butyl-4-nitro-1H-pyrazole
• 英文别名: 1-Butyl-4-nitropyrazole
• CAS: 1240574-64-4
• 化学式: C₇H₁₁N₃O₂
• mdl: MFCD16810712
• 分子量: 169.183
• InChiKey: CQFDLUGTBUUXMU-UHFFFAOYSA-N

物化性质

• 沸点：
  279.7±13.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 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-丁基-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-butyl-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：

  正溴丁烷 、 4-硝基吡唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以84%的产率得到1-丁基-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

• [EN] INDAZOLE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS D'INDAZOLE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013024011A1

  公开（公告）日：2013-02-21

  A compound of formula I: stereoisomers or a pharmaceutically acceptable salt thereof, wherein X, X1, X2, X3, R1, R2, R3, R4, R5 and R6 are described herein, compositions including the compounds and methods of making and using the compounds for the treatment of diseases.

  公式I的化合物：其立体异构体或其药学上可接受的盐，其中X、X1、X2、X3、R1、R2、R3、R4、R5和R6如本文所述，包括该化合物的组合物以及用于治疗疾病的制备和使用该化合物的方法。
• 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。
• 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.
• INDAZOLE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：F.Hoffmann-La Roche AG

  公开号：EP2742040A1

  公开（公告）日：2014-06-18
• Regioselective and Guided C–H Activation of 4-Nitropyrazoles
  作者：Viktor O. Iaroshenko、Ashot Gevorgyan、Olena Davydova、Alexander Villinger、Peter Langer

  DOI：10.1021/jo4025418

  日期：2014.4.4

  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.