2-(m-methylphenoxy)-5-nitropyridine | 28232-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(m-methylphenoxy)-5-nitropyridine
• 英文别名: 5-Nitro-2-(m-tolyloxy)pyridine；2-(3-methylphenoxy)-5-nitropyridine
• CAS: 28232-33-9
• 化学式: C₁₂H₁₀N₂O₃
• 分子量: 230.223
• InChiKey: QRZXIWFKHXBUFD-UHFFFAOYSA-N

物化性质

• 沸点：
  348.1±27.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(m-methylphenoxy)-5-nitropyridine 、 sodium methylate 以 甲醇 、 二甲基亚砜 为溶剂， 生成 5-硝基-2-甲氧基吡啶
  参考文献：
  名称：

  在强碱性介质中的反应。第9部分。在甲醇二甲基亚砜中，由甲氧基催化的1-取代的2,4-二硝基苯和2-取代的5-硝基吡啶的甲醇分解速率与酸度函数的相关性。机械通路的细节

  摘要：

  在甲醇DMSO中，在20.0或21.0°C下，测量了一系列1-取代的2,4-二硝基苯和2-取代的5-硝基吡啶的甲醇盐催化的甲醇分解的速率系数。对于2-取代的5-硝基吡啶和对于低于ca的1-取代的2，4-二硝基苯。55 mol％DMSO，速率与介质的酸度函数相关。讨论了这些线性关系的斜率。高于ca的1-取代的2,4-二硝基苯。55mol％的DMSO产生Meisenheimer络合物作为中间体和/或反应产物。然后，反应产物变为甲醇盐和2,4-二硝基苯甲醚的1,1-Meisenheimer络合物。对于1-氟底物，后者的形成决定了速率。对于其他1个取代的底物，1,3-Meisenheimer配合物的分解将决定速率。

  DOI：

  10.1039/p29870000189
• 作为产物：
  描述：

  2-氯-5-硝基吡啶 、 sodium 3-methylphenoxide 以 甲醇 为溶剂， 生成 2-(m-methylphenoxy)-5-nitropyridine
  参考文献：
  名称：

  Kinetics of the reaction of 2-chloro-3-nitro- and 2-chloro-5-nitropyridines with aryloxide ions in methanol

  摘要：

  The kinetics of the reaction of 2-chloro-3-nitropyridine (ortho-like) and 2-chloro-5-nitropyridine (para-like) with a series of aryloxide ions were studied in methanol at different temperatures. Plots of Delta H-not equal versus Delta S-not equal for both reactions gave good straight lines with isokinetic temperatures of 168 and 195 degrees C. Good linear relationships were obtained from the plots of log k(2) against sigma degrees values with relatively large negative rho values indicating the formation of Meisenheimer sigma-complex intermediates. Plots of log k(2) against pK(a) values gave good straight lines indicating that the reactions show an appreciable degree of bond formation in the transition state. An addition-elimination mechanism is suggested. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199904)12:4<347::aid-poc134>3.0.co;2-g

文献信息

• Reactions in strongly basic media. Part 9. Correlation of the rates of methoxide-catalysed methanolysis of 1-substituted 2,4-dinitrobenzenes and 2-substituted 5-nitropyridines in methanolic dimethyl sulphoxide with an acidity function. Details of the mechanistic pathway
  作者：Keith Bowden、Nighat S. Nadvi

  DOI：10.1039/p29870000189

  日期：——

  measured in methanolic DMSO at 20.0 or 21.0 °C. For the 2-substituted 5-nitropyridines and for the 1-substituted 2,4-dinitrobenzenes below ca. 55 mol% DMSO, the rates have been correlated with an acidity function of the medium. The slopes of these linear relations are discussed. The 1-substituted 2,4-dinitrobenzenes above ca. 55 mol% DMSO give rise to Meisenheimer complexes as intermediates and/or as the

  在甲醇DMSO中，在20.0或21.0°C下，测量了一系列1-取代的2,4-二硝基苯和2-取代的5-硝基吡啶的甲醇盐催化的甲醇分解的速率系数。对于2-取代的5-硝基吡啶和对于低于ca的1-取代的2，4-二硝基苯。55 mol％DMSO，速率与介质的酸度函数相关。讨论了这些线性关系的斜率。高于ca的1-取代的2,4-二硝基苯。55mol％的DMSO产生Meisenheimer络合物作为中间体和/或反应产物。然后，反应产物变为甲醇盐和2,4-二硝基苯甲醚的1,1-Meisenheimer络合物。对于1-氟底物，后者的形成决定了速率。对于其他1个取代的底物，1,3-Meisenheimer配合物的分解将决定速率。
• Kinetics of the reaction of 2-chloro-3-nitro- and 2-chloro-5-nitropyridines with aryloxide ions in methanol
  作者：Ali A. El-Bardan

  DOI：10.1002/(sici)1099-1395(199904)12:4<347::aid-poc134>3.0.co;2-g

  日期：1999.4

  The kinetics of the reaction of 2-chloro-3-nitropyridine (ortho-like) and 2-chloro-5-nitropyridine (para-like) with a series of aryloxide ions were studied in methanol at different temperatures. Plots of Delta H-not equal versus Delta S-not equal for both reactions gave good straight lines with isokinetic temperatures of 168 and 195 degrees C. Good linear relationships were obtained from the plots of log k(2) against sigma degrees values with relatively large negative rho values indicating the formation of Meisenheimer sigma-complex intermediates. Plots of log k(2) against pK(a) values gave good straight lines indicating that the reactions show an appreciable degree of bond formation in the transition state. An addition-elimination mechanism is suggested. Copyright (C) 1999 John Wiley & Sons, Ltd.