3-(4-methylbenzenesulfenyl)-2-pyridone | 107383-65-3

• 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)-2-pyridone
• 英文别名: 3-(p-tolylthio)-2-pyridone；3-[(4-Methylphenyl)sulfanyl]pyridin-2(1H)-one；3-(4-methylphenyl)sulfanyl-1H-pyridin-2-one
• CAS: 107383-65-3
• 化学式: C₁₂H₁₁NOS
• 分子量: 217.291
• InChiKey: OVVCMDDARMSAQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-methylbenzenesulfenyl)-2-pyridone 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 三乙胺 、 lithium hexamethyldisilazane 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-methylphenyl)sulfanyl-1-oxidopyridin-1-ium 、 三氟乙酸酐 以92%的产率得到
  参考文献：
  名称：

  BATMANGHELICH, SHARIAR;TURNER, JOHN R., J. CHEM. RES. SYNOP.,(1987) N 11, 378-379

  摘要：

  DOI：

文献信息

• Silver‐Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions
  作者：Rajasekar Reddy Annapureddy、Finn Burg、Johannes Gramüller、Tino P. Golub、Christian Merten、Stefan M. Huber、Thorsten Bach

  DOI：10.1002/anie.202016561

  日期：2021.3.29

  An enantioselective sulfimidation of 3‐thiosubstituted 2‐quinolones and 2‐pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver‐based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding

  使用化学计量氮宾源 (PhI=NNs) 和银基催化剂体系实现了 3-硫代取代的 2-喹诺酮和 2-吡啶酮的对映选择性硫酰化。该反应成功的关键是使用具有氢键位点的手性菲咯啉配体。对映选择性不取决于硫原子上两个取代基的大小，而仅取决于杂环内酰胺的结合性质。总共 21 种手性硫酰亚胺以高产率 (44–99%) 获得，且对映体过量 (70–99% ee )。磺酰亚胺化反应具有高位点选择性，也可用于手性亚砜的动力学拆分。机理证据表明杂配银络合物的中介作用，其中银原子与一个手性配体分子和一个非手性 1,10-菲咯啉分子结合。 ESI 质谱、DFT 计算和 Hammett 分析支持了所建议的反应过程。
• BATMANGHELICH, SHARIAR;TURNER, JOHN R., J. CHEM. RES. SYNOP.,(1987) N 11, 378-379
  作者：BATMANGHELICH, SHARIAR、TURNER, JOHN R.

  DOI：——

  日期：——
• 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.