2-(N-methylamino)-3-methyl-4-nitropyridine N-oxide | 220899-34-3

• 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
• 英文名称: 2-(N-methylamino)-3-methyl-4-nitropyridine N-oxide
• 英文别名: 2-methylamino-3-methyl-4-nitropyridine N-oxide
• CAS: 220899-34-3
• 化学式: C₇H₉N₃O₃
• 分子量: 183.167
• InChiKey: QVDRLKCASJOMKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.6±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.11
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(N-methylamino)-3-methyl-4-nitropyridine N-oxide 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.33h， 以81%的产率得到3-methyl-2-methylnitrosoamino-4-nitropyridine
  参考文献：
  名称：

  2-烷基亚硝基氨基-4-硝基吡啶和 N-氧化物的 1H、13C 和 15N NMR 研究：sp3 氮的受限反转示例

  摘要：

  摘要 已指定了七个 2-烷基亚硝基氨基-4-硝基吡啶和七个 2-烷基亚硝基氨基-4-硝基吡啶 N-氧化物的 1 H、 13 C 和 15 N NMR 化学位移。已经计算了能量优化结构的 GIAO/DFT 13 C 化学位移。将结果与先前研究的 4-硝基吡啶和 4-硝基吡啶 N-氧化物的 2-烷基氨基和 2-烷基硝氨基衍生物的化学位移进行比较。在空间拥挤的邻位取代同源物（2-乙基亚硝基氨基-3-甲基-4-硝基吡啶N-氧化物）中，锥形氨基氮的限制性反转在分子中形成手性中心并使N-CH 2 -部分的孪生质子非对映。在 5- 和 6-CH 3 - 取代的衍生物中，这种非对映性消失了，但是在所有同族物中围绕 N-CH 2 σ 键的旋转在 NMR 时间尺度上非常缓慢，可以检测到两个构象异构体的 1 H、 13 C 和 15 N NMR 化学位移。在 4-硝基吡啶和 4-硝基吡啶 N-氧化物衍生物中，芳

  DOI：

  10.1016/j.molstruc.2006.07.040
• 作为产物：
  描述：

  2-氯-3-甲基-4-硝基吡啶 1-氧化物 、 甲胺 以 甲醇 为溶剂， 反应 5.0h， 以71%的产率得到2-(N-methylamino)-3-methyl-4-nitropyridine N-oxide
  参考文献：
  名称：

  Synthesis of nitro derivatives of 2-alkylamino-4-nitropicolines and their N-oxides

  摘要：

  DOI：

  10.1007/bf02290941

文献信息

• Solvent effect and quantum chemical calculations of the electron energy levels for nitro derivatives of 2-(N-methylamino)-picolines
  作者：J. Lorenc

  DOI：10.1016/j.molstruc.2005.03.017

  日期：2005.6

  Electronic absorption spectra of 2-(N-methylamino)-3-methyl-4-nitropyridine (M3M4NP), 2- (N-methylamino)-5-methyl-4-nitropyridine (M5M4NP), 2-(N-methylamino)-3-methyl-5-nitropyridine (M3M5NP) and 2-(N-methylamino)-5-methyl-3-nitropyridine (M5M3NP) in the ethyl alcohol, acetonitrile and n-heptane solution as well as solid state have been measured at room temperature. The influence of the solvent and substitution on polar and non-polar properties has been discussed. The results obtained by the ab initio TD DFT quantum calculations using MPW1PW91 and B3LYP functional and 6-31G(d,p) basis have been compared with that of experimental values. (c) 2005 Elsevier B.V. All rights reserved.
• Excited electronic states of 2-ethylamino-(3 or 5)-methyl-4-nitropyridine and 2-methylamino-(3 or 5)-methyl-4-nitropyridine
  作者：J. Lorenc、E. Kucharska、J. Hanuza、H. Chojnacki

  DOI：10.1016/j.molstruc.2004.05.029

  日期：2004.11

  Electronic absorption spectra of 2-methylamino-, 2-ethylamino-3-methyl-4-nitropyridine and 2-ethylamino-, 2-methylamino-5-methyl-4-nitropyridine in the solid state and ethyl alcohol solution have been measured at room temperature. Their luminescence spectra and life times have been recorded at room and liquid helium temperatures. The energy sequence of the singlet and triplet states has been calculated for optimised geometry of the molecules and compared to the experimental values. The results of ab initio TD DFT quantum calculations using MPW1PW91 density functional 6-31G(d,p) basis set have been analysed. (C) 2004 Elsevier B.V. All rights reserved.
• Structure–activity relationship disturbed by a solvolytic process: Study on the [Cu(II)-4-nitropyridine N-oxide derivative] system
  作者：Aniela Puszko、Andrzej Kochel、Joanna Wietrzyk、Beata Filip-Psurska、Julia Jezierska、Mariola Puszyńska-Tuszkanow、Zbigniew Staszak、Anna Adach、Jadwiga Lorenc、Maria Cieslak-Golonka

  DOI：10.1016/j.poly.2012.09.060

  日期：2013.2

  The chelate complex [CuCl2(L)] where L = 2-methylamino-3-methyl-4-nitropyridine-N-oxide has been obtained and characterized, both physicochemically (by the X-ray structure analysis of the complex and the ligand, FTIR, EPR and electronic spectroscopy, and thermal analysis) and cytotoxically (MCF-7, A549, SW707, P388, Balb3T3). In solution, atypically for chelate complexes, it undergoes rapid solvolysis forming various 6- (or 5) and 4-coordinate species, depending upon the solvent. Such rapid decomposition may indicate a catalytic effect of the copper operating in the system. However, the cytotoxic activity in solution for the new copper chelate complex appeared to be a surprisingly low. Thus, before drawing any conclusions on the structure-activity relationship, one must carefully check the chemical identity of the compound(s) in both phases. (C) 2012 Elsevier Ltd. All rights reserved.