3-(4"-methylbenzenesulfenyl)-1-(4'-methylbenzenesulfonyl)-2-pyridone | 141667-32-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(4"-methylbenzenesulfenyl)-1-(4'-methylbenzenesulfonyl)-2-pyridone
• 英文别名: 3-(4-Methylphenyl)sulfanyl-1-(4-methylphenyl)sulfonylpyridin-2-one
• CAS: 141667-32-5
• 化学式: C₁₉H₁₇NO₃S₂
• 分子量: 371.481
• InChiKey: QIMHTWKXUURDQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4"-methylbenzenesulfenyl)-1-(4'-methylbenzenesulfonyl)-2-pyridone 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 126.33h， 生成 methyl <<(tert-butyldimethylsilyl)oxy>methyl>-4β-<(4'-methylbenzenesulfonyl)amino>cyclohexene-1-carboxylate
  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
• 作为产物：
  描述：

  3-(4-methylbenzenesulfenyl)-2-pyridone 、 对甲苯磺酰氯 在 lithium hexamethyldisilazane 作用下， 生成 3-(4"-methylbenzenesulfenyl)-1-(4'-methylbenzenesulfonyl)-2-pyridone
  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