N-[4-(p-tolylthio)phenyl]acetamide | 339096-10-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-[4-(p-tolylthio)phenyl]acetamide
• 英文别名: 4-(p-tolylthio)acetanilide；acetic acid-(4-p-tolylsulfanyl-anilide)；Essigsaeure-(4-p-tolylmercapto-anilid)；(4-Acetamino-phenyl)-p-tolyl-sulfid；N-{4-[(4-methylphenyl)sulfanyl]phenyl}acetamide；N-[4-(4-methylphenyl)sulfanylphenyl]acetamide
• CAS: 339096-10-5
• 化学式: C₁₅H₁₅NOS
• 分子量: 257.356
• InChiKey: PMAHLXRQZPRIGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  N-[4-(p-tolylthio)phenyl]acetamide 在 硝酸 作用下， 生成 (+/-)-4-(acetamino)phenyl 4-methylphenyl sulfoxide
  参考文献：
  名称：

  v.Meyer,E.; Heiduschka, Journal fur praktische Chemie (Leipzig 1954), 1903, vol. <2>68, p. 278

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲苯硫酚 在 磺酰氯 、 三氟甲磺酸 、 bis(4-methoxyphenyl)selenide 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 18.25h， 生成 N-[4-(p-tolylthio)phenyl]acetamide
  参考文献：
  名称：

  Lewis Base/Bronsted Acid Dual-Catalytic C–H Sulfenylation of Aromatics

  摘要：

  A Lewis base/Bronsted acid catalyzed aromatic sulfenylation is reported. These studies demonstrated that the incorporation of electron-rich sulfenyl groups proceeded in the absence of a Lewis base, with kinetic studies indicating an autocatalytic mechanism. The incorporation of electron-poor sulfenyl groups demonstrated little autocatalysis necessitating the use of a Lewis base. This method proved amenable to diverse arenes and heterocycles and was effective in the context of the late-stage functionalization of biologically active small molecules.

  DOI：

  10.1021/acs.orglett.8b01066

文献信息

• A Highly Efficient, Ligand-Free, and Recyclable Cu2S-Catalyzed Coupling of Aryl Iodides with Diaryl Disulfides
  作者：Huifeng Wang、Linlin Jiang、Tao Chen、Yaming Li

  DOI：10.1002/ejoc.201000003

  日期：2010.4

  A highly efficient and ligand-free copper(I) sulfide catalyzed cross-coupling reaction of aryl iodides with diaryl disulfides was developed. With only 1 mol-% of Cu 2 S as the catalyst, iron powder as the reductant, and K 2 CO 3 as the base, aryl iodides reacted with disulfides in DMSO at 90-110°C for 18-24 h under an atmosphere of argon to give the corresponding aryl sulfides in good to excellent

  开发了一种高效且无配体的硫化铜（I）催化芳基碘化物与二芳基二硫化物的交叉偶联反应。以1 mol%的Cu 2 S为催化剂，铁粉为还原剂，K 2 CO 3 为碱，芳基碘化物与二硫化物在DMSO中在90-110°C的气氛下反应18-24 h氩以良好至极好的产率得到相应的芳基硫化物。此外，催化剂是可回收和可重复使用的，但会损失一些活性。
• Direct thioether metathesis enabled by <i>in situ</i> formed Pd nanocluster catalysts
  作者：Takehiro Matsuyama、Takafumi Yatabe、Tomohiro Yabe、Kazuya Yamaguchi

  DOI：10.1039/d3cy01563g

  日期：——

  has not been previously reported. Herein, direct catalytic metathesis of various thioethers was enabled by Pd acetate and tricyclohexylphosphine precursors with no additives, affording unsymmetrical thioethers. Detailed characterization and control experiments confirmed that Pd(0) nanocluster homogeneous catalysts formed in situ are the actual active species enabling this versatile direct transformation

  硫醚复分解被认为是一种具有交叉偶联反应的补充硫醚合成方法，可应用于后期多样化。然而，尽管它具有实用性，但硫醚的多功能直接 C-S/C-S 交叉复分解尚未见报道。在此，通过乙酸钯和三环己基膦前体在不添加任何添加剂的情况下直接催化复分解各种硫醚，得到不对称硫醚。详细的表征和控制实验证实，原位形成的 Pd(0) 纳米团簇均相催化剂是实现这种多功能直接转化的实际活性物质。这项工作将为金属纳米簇催化剂驱动的新型有机分子转化铺平道路。
• v.Meyer,E.; Heiduschka, Journal fur praktische Chemie (Leipzig 1954), 1903, vol. <2>68, p. 265
  作者：v.Meyer,E.、Heiduschka

  DOI：——

  日期：——
• [EN] CAPREOMYCIN DERIVATIVES AND THEIR USE AS ANTIBACTERIALS<br/>[FR] DÉRIVÉS DE CAPRÉOMYCINE, ET LEUR UTILISATION EN TANT QU'AGENTS ANTIBACTÉRIENS
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2007130743A2

  公开（公告）日：2007-11-15

  [EN] The present invention relates to phenylurea derivatives of capreomycin I, IIB, IIA, or IB, and metabolites and pharmaceutically acceptable salts and solvates thereof. The compounds of the present invention are useful as antibacterial agents for treating bacterial infections and for treating disorders caused by bacterial infections. The present invention also relates to pharmaceutical compositions containing such compounds and to methods of treating bacterial infections by administering such compounds. The present invention also relates to methods of preparing such compounds.
  [FR] L'invention concerne des dérivés de phénylurée de capréomycine I, IIB, IIA, ou IB, ainsi que des métabolites, des sels pharmaceutiquement acceptables et des solvates de ces composés. Les composés selon l'invention peuvent servir d'agents antibactériens pour traiter des infections bactériennes, ainsi que pour traiter des troubles causés par des infections bactériennes. Cette invention se rapporte en outre à des compositions pharmaceutiques comprenant lesdits composés, ainsi qu'à des procédés pour traiter des infections bactériennes par administration de ces composés. La présente invention concerne en outre des procédés pour préparer lesdits composés.
• Lewis Base/Bronsted Acid Dual-Catalytic C–H Sulfenylation of Aromatics
  作者：Christopher J. Nalbandian、Zachary E. Brown、Erik Alvarez、Jeffrey L. Gustafson

  DOI：10.1021/acs.orglett.8b01066

  日期：2018.6.1

  A Lewis base/Bronsted acid catalyzed aromatic sulfenylation is reported. These studies demonstrated that the incorporation of electron-rich sulfenyl groups proceeded in the absence of a Lewis base, with kinetic studies indicating an autocatalytic mechanism. The incorporation of electron-poor sulfenyl groups demonstrated little autocatalysis necessitating the use of a Lewis base. This method proved amenable to diverse arenes and heterocycles and was effective in the context of the late-stage functionalization of biologically active small molecules.