2-acetamidophenyl 4-methylbenzenesulfonate | 959085-52-0

• 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: 2-acetamidophenyl 4-methylbenzenesulfonate
• 英文别名: O-tosyl-2-(acetamido)phenol；toluene-4-sulfonic acid 2-acetylamino-phenyl ester；o-(p-tolylsulfonoxy) acetanilide；1-acetylamino-2-(toluene-4-sulfonyloxy)-benzene；Toluol-sulfonsaeure-(4)-(2-acetamino-phenylester)；2-Acetamino-1-(toluol-sulfonyl-(4)-oxy)-benzol；1-Acetylamino-2-(toluol-4-sulfonyloxy)-benzol；N-Acetyl-O-p-toluenesulfonyl-2-aminophenol；(2-acetamidophenyl) 4-methylbenzenesulfonate
• CAS: 959085-52-0
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: ZSLKQUSNWOUAAU-UHFFFAOYSA-N

物化性质

• 熔点：
  134 °C
• 沸点：
  525.9±50.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetamidophenyl 4-methylbenzenesulfonate 在 水 、 硝酸 作用下， 生成 1-acetylamino-4-nitro-2-(toluene-4-sulfonyloxy)-benzene
  参考文献：
  名称：

  CCCXXII。—硝基氨基酚与磺酰氯的相互作用

  摘要：

  DOI：

  10.1039/jr9310002343
• 作为产物：
  描述：

  N-Phenylacetohydroxamic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-acetamidophenyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Photoacid generators (PAGs) based on N-acyl-N-phenylhydroxylamines for carboxylic and sulfonic acids

  摘要：

  Simple and efficient photoacid generators (PAGs) for carboxylic and sulfonic acids based on N-acyl-N-phenylhydroxylamines have been demonstrated. Irradiation of o-carboxylates and thermally rearranged o-arenesulfonates of N-acyl-N-phenylhydroxylamines using UV light (>= 254 nm) in aqueous methanolic solution resulted in efficient generation of carboxylic and sulfonic acids, respectively. The carboxylic acid generation ability of N-acyl-N-phenylhydroxylamines was found to be dependent on their N-acyl substituents. Further, polymer bearing o-arenesulfonates of N-acyl-N-phenylhydroxylamine was synthesized and demonstrated as PAG for sulfonic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.049

文献信息

• Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives
  作者：Ling Lin、Xiaoguang Chen、Junhao Zhao、Suitao Lin、Guojian Ma、Xiaojian Liao、Pengju Feng

  DOI：10.1515/hc-2019-0017

  日期：2019.12.19

  Abstract This paper discloses an efficient one-pot protocol to convert easily accessible 3-nitropyridines to 3-acetamidopyridin-2-yl 4-methylbenzenesulfonate derivatives which are core structures of many pharmaceutical molecules. The strategy successfully combined a three-step reaction in one pot via progressively adding different reactants at rt. The reaction displays good functional group tolerance

  摘要 本文公开了一种有效的一锅法，可将易于获得的 3-硝基吡啶转化为 3-乙酰氨基吡啶-2-基 4-甲基苯磺酸衍生物，这是许多药物分子的核心结构。该策略通过在室温下逐步添加不同的反应物，成功地将三步反应合二为一。该反应显示出良好的官能团耐受性和区域选择性。结构多样化的 3-硝基吡啶可以高效地（3.5 小时）衍生为各种功能性 2-O,3-N-吡啶，适合进一步阐述。该转化适用于克级合成。
• [EN] A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH ARYL TOSYLATES<br/>[FR] PROCÉDÉ POUR LE COUPLAGE CATALYSÉ PAR LE PALLADIUM D'ALCYNES TERMINALES AVEC DES TOSYLATES D'ARYLE
  申请人：SANOFI AVENTIS

  公开号：WO2009003589A1

  公开（公告）日：2009-01-08

  The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process for aryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional aryl-1-alkynes of the formula (I) useful for the production of intermediates in the preparation for pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.

  本发明涉及一种用于选择性合成公式(I)化合物的过程，其中R1；R2；R3；R4；R5；J和W具有声明中指示的含义。本发明提供了一种高效和通用的钯催化偶联过程，可将芳基磺酸酯与末端炔烃偶联，形成一系列取代的、多功能的芳基-1-炔烃，其化学式为(I)，用于制备制药品、诊断试剂、液晶、聚合物、除草剂、杀菌剂、线虫杀灭剂、寄生虫杀灭剂、杀虫剂、螨虫剂和节肢动物杀灭剂的中间体。
• A General Palladium-Catalyzed Sonogashira Coupling of Aryl and Heteroaryl Tosylates
  作者：Omar R'kyek、Nis Halland、Andreas Lindenschmidt、Jorge Alonso、Peter Lindemann、Matthias Urmann、Marc Nazaré

  DOI：10.1002/chem.201001524

  日期：2010.9.3

  Coupled up: A new general palladium‐catalyzed procedure for the cross‐coupling of aryl and heteroaryl tosylates is described. This highly versatile and efficient process can be used for the synthesis of a wide variety of functionalized alkynes (see scheme).

  耦合：描述了一种新的通用钯催化的芳基和杂芳基甲苯磺酸盐的交叉偶联方法。这种高度通用和高效的方法可用于合成多种功能化的炔烃（请参见方案）。
• Sulfonylation-Induced <i>N</i>- to <i>O</i>-Acetyl Migration in 2-Acetamidoethanol Derivatives
  作者：Takao Yamaguchi、Dusan Hesek、Mijoon Lee、Allen G. Oliver、Shahriar Mobashery

  DOI：10.1021/jo100456z

  日期：2010.5.21

  example of sulfonylation-induced N- to O-acetyl migration of 2-acetamidoethanol derivatives is described. This type of reaction could happen with any 2-acetamidoethanol derivatives under typical sulfonylation conditions (TsCl or MsCl, pyridine) and might be a common side reaction of significance. Furthermore, the results reveal that 2-acetamidoethanol derivatives with a sterically encumbered hydroxyl

  描述了磺酰化诱导的N - 到O - 乙酰基迁移的 2-乙酰氨基乙醇衍生物的第一个例子。在典型的磺酰化条件（TsCl 或 MsCl、吡啶）下，任何 2-乙酰氨基乙醇衍生物都可能发生这种类型的反应，并且可能是一种常见的重要副反应。此外，结果表明，具有空间位阻羟基的 2-乙酰氨基乙醇衍生物可产生高产率的迁移产物。讨论了迁移反应的机理。
• Process for the palladium-catalyzed coupling of terminal alkynes with aryl tosylates
  申请人：RKYEK Omar

  公开号：US20100261910A1

  公开（公告）日：2010-10-14

  The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process for aryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional aryl-1-alkynes of the formula I.

  本发明涉及一种合成式(I)化合物的区域选择性合成方法，其中R1、R2、R3、R4、R5、J和W的含义如权利要求所示。本发明提供了一种高效、通用的钯催化偶联方法，用于将芳基磺酸酯与末端炔烃耦合成式I的多取代多功能芳基-1-炔烃。