2-methyl-4-nitro-1-phenyl-1H-imidazole | 41384-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-4-nitro-1-phenyl-1H-imidazole
• 英文别名: 1-phenyl-2-methyl-4-nitroimidazole；2-methyl-4-nitro-1-phenylimidazole
• CAS: 41384-82-1
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: QEDFIVOBVCLEML-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C(Solv: methanol (67-56-1))
• 沸点：
  397.0±34.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：

  2-methyl-4-nitro-1-phenyl-1H-imidazole 在 sodium sulfide 、 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以15%的产率得到5-methyl-3-(N-phenylcarbamathioyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Suwinski, Jerzy; Pawlus, Wojciech; Salwinska, Ewa, Heterocycles, 1994, vol. 37, # 3, p. 1511 - 1520

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯磺酸盐二溴苯基碘 、 2-甲基-4-硝基咪唑 在 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以81%的产率得到2-methyl-4-nitro-1-phenyl-1H-imidazole
  参考文献：
  名称：

  Regioselective N-arylation of nitroazoles. Determination of the structure of N-arylnitro-azoles on the basis of NMR spectroscopic data and quantum-chemical calculations

  摘要：

  The N-arylation of a series of nitroazoles has been studied with the aid of diaryliodonium salts in the presence of CuI under the action of microwave radiation. It was found that alkylation proceeds regioselectively in each actual case with the formation of one of two possible isomers. The correct structure of the N-arylation products was established on the basis of NMR spectroscopy.

  DOI：

  10.1007/s10593-011-0718-z

文献信息

• Oximes as intermediates or final products in reactions of nitroheteroarenes with nucleophiles in the presence of sodium methoxide-methanol system
  作者：J. Suwińaski、K. Świerczek、P. Wagner、M. Kubicki、T. Borowiak、J. Stowikowska

  DOI：10.1002/jhet.5570400318

  日期：2003.5

  been shown that reactions of 4-nitroimidazoles and some other nitroaromatic systems with phenyl-acetonitrile in the presence of sodium methoxide in methanol lead to the reduction of the nitro to nitroso group and to the nucleophilic displacement of hydrogen atom at the ring by the respective carbanion followed by tautomerization of the nitroso compound to an oxime. Similar reactions of 4-nitroimidazoles

  已经表明，在甲醇中存在甲醇钠的情况下，4-硝基咪唑和其他一些硝基芳族体系与苯基乙腈的反应会导致硝基还原为亚硝基，并导致环上氢原子的亲核取代。各自的碳负离子，然后将亚硝基化合物互变异构为肟。4-硝基咪唑与诸如由4-氨基-1,2,4-三唑生成的阴离子之类的亲核试剂的类似反应随着咪唑环化成1,2,4-恶二唑衍生物而发生，有时在反应介质中经历进一步的过程。通过X射线衍射分析已经确认了一些产品的结构。
• Reduction of aromatic nitrocompounds by sodium borohydride in methanol in the presence of sodium methoxide
  作者：Jerzy Suwiński、Pawel Wagner、Elizabeth M. Holt

  DOI：10.1016/0040-4020(96)00491-7

  日期：1996.7

  The paper presents the results of the reduction of 4-nitroimidazoles, 4-nitropyrazoles and 3-nitropyridines by sodium borohydride or sodium borodeuteride in methanol in the presence of sodium methoxide, 1-Substituted 4-nitroimidazoles yield oximes of 4-imidazolidinones, the nitropyrazoles and nitropyridines yield respective azoxy compounds. The reaction mechanism proposed in the work makes allowances

  本文介绍了在甲醇钠存在下在甲醇中用硼氢化钠或硼氢化氘化钠还原4-硝基咪唑，4-硝基吡唑和3-硝基吡啶的结果，1-取代的4-硝基咪唑生成4-咪唑啉酮的肟，硝基吡唑硝基吡啶和硝基吡啶分别产生氮杂化合物。在工作中提出的反应机理考虑了甲醇甲醇体系的催化作用。
• Synthesis and photochemical behaviour of 4-nitroimidazoles in the presence of oxygen
  作者：Maurizio D'Auria、Franco D'Onofrio、Jerzy Suwinski、Krzysztor Swierczek

  DOI：10.1016/s0040-4020(01)90240-6

  日期：1993.4

  Synthesis and photochemical properties of 1-aryl-4-nitroimidazoles are described. These compounds are good sensitizers of superoxide ion. Only 1-phenyl-2-methyl-4-nitroimidazole is a photosensitizer of singlet oxygen.

  描述了1-芳基-4-硝基咪唑的合成和光化学性质。这些化合物是超氧化物离子的良好敏化剂。只有1-苯基-2-甲基-4-硝基咪唑是单线态氧的光敏剂。
• Practical copper-catalyzed N-arylation of amines with 20% aqueous solution of n-Bu4NOH
  作者：Hamidreza Molaei、Mohammad Mehdi Ghanbari

  DOI：10.1016/j.cclet.2011.12.015

  日期：2012.3

  N-Arylation of a wide variety of amines with phenylboronic acid catalyzed by copper acetate under 20% aqueous solution of n-Bu4NOH was accomplished in good to excellent yields (up to 92%) and substrate conversions (up to 96%). (C) 2011 Mohammad Mehdi Ghanbari. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Suwinski, J.; Walczak, K., Polish Journal of Chemistry, 1994, vol. 68, # 4, p. 675 - 682
  作者：Suwinski, J.、Walczak, K.

  DOI：——

  日期：——