2-(p-toluenesulfonyloxy)-3-methoxy-pyridine | 141667-62-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(p-toluenesulfonyloxy)-3-methoxy-pyridine
• 英文别名: (3-Methoxypyridin-2-yl) 4-methylbenzenesulfonate
• CAS: 141667-62-1
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: IRNUMLRGFPUHJS-UHFFFAOYSA-N

物化性质

• 熔点：
  74-76 °C
• 沸点：
  450.0±45.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-methoxy-1-tosylpyridin-2(1H)-one 以 二氯甲烷 为溶剂， 反应 21.0h， 以27%的产率得到2-(p-toluenesulfonyloxy)-3-methoxy-pyridine
  参考文献：
  名称：

  Diels-Alder cycloadditions using nucleophilic 2-pyridones. Regiocontrolled and stereocontrolled synthesis of unsaturated, bridged, bicyclic lactams

  摘要：

  Captodative 3-oxy-and 3-(tolylthio)-1-tosyl-2-pyridones 1a-1d are shown to be reactive as nucleophilic dienes undergoing 2 + 4-cycloadditions with various electrophilic alkenes under sufficiently mild thermal conditions (90-100-degrees-C) that the initial bicylic lactam adducts can be isolated on gram scale in fair to very good yields (23-83%) without loss of an isocyanate from the heteroatom bridge. These bicyclic adducts are formed with complete regiocontrol and stereocontrol. For pyridone sulfide 1d, these Diels-Alder cycloadditions are the first examples of a captodative unsaturated sulfide acting as an enophile. NMR data (C-13) are presented correlating the electron density in the pyridone diene systems with their Diels-Alder reactivity, and some transformations of the bicyclic lactam adducts are shown to illustrate the value and versatility of these richly functionalized synthetic intermediates.

  DOI：

  10.1021/jo00041a010

文献信息

• One-Step Conversion of Azine <i>N</i>-Oxides to α-1,2,4-Triazolo-, 1,2,3-Triazolo, Imidazolo-, and Pyrazoloheteroarenes
  作者：John M. Keith

  DOI：10.1021/jo1001017

  日期：2010.4.16

  Pyridine, quinoline, isoquinoline, azaindole, and pyrimidine N-oxides were converted to their alpha-triazole and alpha-diazole derivatives by treatment with the corresponding p-toluenesulfonylazoles and Hunig's base at elevated temperatures.
• Diels-Alder cycloadditions using nucleophilic 2-pyridones. Regiocontrolled and stereocontrolled synthesis of unsaturated, bridged, bicyclic lactams
  作者：Gary H. Posner、Victoria Vinader、Kamyar Afarinkia

  DOI：10.1021/jo00041a010

  日期：1992.7

  Captodative 3-oxy-and 3-(tolylthio)-1-tosyl-2-pyridones 1a-1d are shown to be reactive as nucleophilic dienes undergoing 2 + 4-cycloadditions with various electrophilic alkenes under sufficiently mild thermal conditions (90-100-degrees-C) that the initial bicylic lactam adducts can be isolated on gram scale in fair to very good yields (23-83%) without loss of an isocyanate from the heteroatom bridge. These bicyclic adducts are formed with complete regiocontrol and stereocontrol. For pyridone sulfide 1d, these Diels-Alder cycloadditions are the first examples of a captodative unsaturated sulfide acting as an enophile. NMR data (C-13) are presented correlating the electron density in the pyridone diene systems with their Diels-Alder reactivity, and some transformations of the bicyclic lactam adducts are shown to illustrate the value and versatility of these richly functionalized synthetic intermediates.
• Highly efficient Diels-Alder cycloadditions of 2-pyridones with bulky N-sulfonyl substituent
  作者：Kamyar Afarinkia、Farzana Mahmood

  DOI：10.1016/s0040-4039(97)10585-8

  日期：1998.1

  The rearrangement of N-sulfonyl pyridones to the corresponding O-sulfonyl pyridinols during cycloaddition can be greatly retarded by introduction of steric congestion on either the pyridone ring or the sulfonyl group. Hence, significantly improved yields of cycloaddition are obtained for N-2,4,6-triisopropylbenzenesulfonyl 2-pyridones. Changes in the electronic nature of various substituents does not significantly alter the rate of migration. (C) 1997 Elsevier Science Ltd. All rights reserved.

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