2,3,6-Trimethyl-4-nitropyridine N-oxide | 38594-55-7

• 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: 2,3,6-Trimethyl-4-nitropyridine N-oxide
• 英文别名: 2,3,6-trimethyl-4-nitropyridine 1-oxide；2,3,6-dimethyl-4-nitropyridine N-oxide；2,3,6-trimethyl-4-nitro-pyridine-1-oxide；2,3,6-Trimethyl-4-nitro-pyridin-1-oxid；2,3,6-Trimethyl-4-nitropyridin-N-oxid；2,3,6-Trimethyl-4-nitropyridine 1-oxide；2,3,6-trimethyl-4-nitro-1-oxidopyridin-1-ium
• CAS: 38594-55-7
• 化学式: C₈H₁₀N₂O₃
• 分子量: 182.179
• InChiKey: YKPBNPIFKOZLBI-UHFFFAOYSA-N

物化性质

• 熔点：
  114 °C
• 沸点：
  414.3±40.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,6-Trimethyl-4-nitropyridine N-oxide 在 盐酸 、 甲醇 、 potassium acetate 、 铁粉 、 钯 、 溶剂黄146 作用下， 生成 2,3,6-三甲基吡啶
  参考文献：
  名称：

  Evans, Journal of the Chemical Society, 1959, p. 1312

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,6-Trimethyl-pyridin-N-oxid 在 硫酸 、 硝酸 作用下， 生成 2,3,6-Trimethyl-4-nitropyridine N-oxide
  参考文献：
  名称：

  Evans, Journal of the Chemical Society, 1959, p. 1312

  摘要：

  DOI：

文献信息

• Metal-free methylation of a pyridine N-oxide C–H bond by using peroxides
  作者：Gang Li、Suling Yang、Bingjie Lv、Qingqing Han、Xingxing Ma、Kai Sun、Zhiyong Wang、Feng Zhao、Yunhe Lv、Hankui Wu

  DOI：10.1039/c5ob01900a

  日期：——

  Metal-free methylation of a pyridine N-oxide C–H bond was developed using peroxide as a methyl reagent under neat conditions. Pyridine N-oxide derivatives with various groups (e.g., Cl, NO₂, and OCH₃) were all suitable substrates.

  使用过氧化物作为甲基试剂，在无溶剂条件下开发了对吡啶N-氧化物C-H键的无金属甲基化方法。具有各种基团（如Cl、NO2和OCH3）的吡啶N-氧化物衍生物均是合适的底物。
• 1H, 13C and 15N NMR spectral and theoretical studies of some methyl and alkylamino derivatives of 4-halopyridine N-oxides
  作者：K. Laihia、A. Puszko、J. Linnanto、E. Kolehmainen

  DOI：10.1016/j.molstruc.2005.01.065

  日期：2006.2

  Nine new and three earlier known 4-halogen (Cl and Br) substituted pyridine N-oxides have been prepared and their H-1, C-13 and N-15 NMR chemical shifts assigned based on PFG H-1, X (X = C-13 and N-15) HMQC and HMBC experiments as well as the comparison with our earlier results for substituted pyridine N-oxide derivatives. The N-15 resonances of the pyridine nitrogen are 27-40 ppm more shielded in 4-halo-2alkylamino-6-methyl-5-nitropyridine N-oxide than in parent 4-halopyridine N-oxide. According to quantum chemical ab initio HF/ 6-311G** calculations the amino tautomer of 4-chloro-2-methylamino-6-methyl-5-nitropyridine N-oxide is more stable than its imino form. Using B3LYP/6-311G** optimized structures both C-13 and N-15 shifts were calculated by density functional B3LYP/6-311G** CSGT methods for the amino and imino tautomers as well as for the dimeric structure for 4-chloro-2-methylamino-6-methyl-5-nitropyridine N-oxide. The 15N NMR and DFT calculations suggest the prevailing of the dimeric amino form for one congener, which is further supported by ESI-TOF MS data. (c) 2005 Elsevier B.V. All rights reserved.
• Evans, Journal of the Chemical Society, 1959, p. 1312
  作者：Evans

  DOI：——

  日期：——