3-methoxy-1-tosylpyridin-2(1H)-one | 141667-29-0

• 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: 3-methoxy-1-tosylpyridin-2(1H)-one
• 英文别名: 3-Methoxy-1-(toluene-4-sulfonyl)-1H-pyridin-2-one；3-Methoxy-1-(4-methylbenzene-1-sulfonyl)pyridin-2(1H)-one；3-methoxy-1-(4-methylphenyl)sulfonylpyridin-2-one
• CAS: 141667-29-0
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: RHTONYXWNYMVLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methoxy-1-tosylpyridin-2(1H)-one 在 正丁基锂 、 barium carbonate 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、1000.0 MPa 条件下， 反应 146.0h， 生成 dimethyl 1β-methoxy-4α-<(4'-methylbenzenesulfonyl)amino>cyclohex-5-ene-1,2-dicarboxylate
  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：

  吡啶-2,3-二醇 在 咪唑 、 三氟化硼乙醚 、 甲基锂 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 63.25h， 生成 3-methoxy-1-tosylpyridin-2(1H)-one
  参考文献：
  名称：

  使用金鸡纳衍生的双功能有机催化剂将 3-羟基-2-吡啶酮对映选择性迈克尔加成到硝基烯烃上

  摘要：

  尽管N-杂芳烃在药物和天然产物中广泛使用，但在2-吡啶酮的C-4位选择性烷基化的有效方法却很少。我们使用金鸡纳衍生的双功能方酰胺有机催化剂开发了 3-羟基-2-吡啶酮对硝基烯烃在 C-4 位的对映选择性迈克尔加成反应，实现了高达 95% 的产率和 >99% ee。这种选择性是由双功能有机催化剂在温和条件下与 3-羟基-2-吡啶酮和硝基烯烃的氢键相互作用驱动的。该方法证明了迈克尔反应对各种硝基烯烃的多功能性，为在环境友好的条件下合成具有高对映选择性和区域选择性的手性N-杂芳烃提供了一种可持续的方法。

  DOI：

  10.1039/d4ob01042f

文献信息

• COMPOSITIONS AND METHODS FOR TREATING COLITIS
  申请人：Aerpio Therapeutics, Inc.

  公开号：EP2954899A1

  公开（公告）日：2015-12-16

  Disclosed herein are compositions and methods for treating colitis and other inflammatory bowel diseases, inter alia, indeterminate colitis, Crohn's disease, irritable bowel syndrome and ischemic colitis.

  本文公开了用于治疗结肠炎和其他炎症性肠病的组合物和方法，其中包括不定型结肠炎、克罗恩病、肠易激综合征和缺血性结肠炎。
• 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.
• 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.
• 10.1039/d4ob01042f
  作者：Gi, Minseok、Oh, Daehyun、Yang, Sehun、Lee, Jaeyong、Jung, So Hyun、Baek, Ju Ha、Ha, Min Woo、Lee, Geumwoo、Park, Hyeung-Geun

  DOI：10.1039/d4ob01042f

  日期：——

  nitroolefins at the C-4 position using cinchona-derived bifunctional squaramide organocatalysts, achieving up to 95% yield and >99% ee. This selectivity is driven by the bifunctional organocatalysts’ hydrogen bonding interactions with 3-hydroxy-2-pyridone and nitroolefins under mild conditions. This method demonstrates the Michael reaction's versatility with various nitroolefins, providing a sustainable

  尽管N-杂芳烃在药物和天然产物中广泛使用，但在2-吡啶酮的C-4位选择性烷基化的有效方法却很少。我们使用金鸡纳衍生的双功能方酰胺有机催化剂开发了 3-羟基-2-吡啶酮对硝基烯烃在 C-4 位的对映选择性迈克尔加成反应，实现了高达 95% 的产率和 >99% ee。这种选择性是由双功能有机催化剂在温和条件下与 3-羟基-2-吡啶酮和硝基烯烃的氢键相互作用驱动的。该方法证明了迈克尔反应对各种硝基烯烃的多功能性，为在环境友好的条件下合成具有高对映选择性和区域选择性的手性N-杂芳烃提供了一种可持续的方法。

表征谱图