4-((4-methoxyphenyl)thio)benzamide | 212691-84-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-((4-methoxyphenyl)thio)benzamide
• 英文别名: 4-[(4-Methoxyphenyl)thio]benzamide；4-(4-methoxyphenyl)sulfanylbenzamide
• CAS: 212691-84-4
• 化学式: C₁₄H₁₃NO₂S
• 分子量: 259.329
• InChiKey: HRCIOVGCHFFSME-UHFFFAOYSA-N

物化性质

• 沸点：
  477.5±30.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 4-碘苯甲酸 在 bis(bipyridine)nickel(II) bromide SPPSLRAM SynPhase Lanterns(R) 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 borohydride polymer supported Amberlite(R) IRA₄₀₀ 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 四氢呋喃 、 乙醇 为溶剂， 反应 30.0h， 以100%的产率得到4-((4-methoxyphenyl)thio)benzamide
  参考文献：
  名称：

  Solid-Phase Synthesis of Diaryl Sulfides: Direct Coupling of Solid-Supported Aryl Halides with Thiols Using an Insoluble Polymer-Supported Reagent

  摘要：

  Diaryl sulfides have been prepared by direct nickel(II)-catalyzed coupling of thiols with iodoaryl bound to SynPhase polystyrene lanterns in the presence of polymer-supported borohydride.

  DOI：

  10.1021/ol050939v

文献信息

• Visible-Light-Promoted C–S Cross-Coupling via Intermolecular Charge Transfer
  作者：Bin Liu、Chern-Hooi Lim、Garret M. Miyake

  DOI：10.1021/jacs.7b07390

  日期：2017.10.4

  Disclosed is a mild, scalable, visible-light-promoted cross-coupling reaction between thiols and aryl halides for the construction of C-S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore

  公开了一种温和的、可扩展的、可见光促进的硫醇和芳基卤化物之间的交叉偶联反应，用于在没有过渡金属和光氧化还原催化剂的情况下构建 CS 键。芳基卤化物和硫醇伙伴的范围包括 60 多个例子，因此提供了进入各种具有药用价值的芳基硫醚构件的切入点。此外，为了证明其效用，该 CS 耦合方案被应用于药物合成和活性药物成分的后期修饰。紫外-可见光谱和时间相关的密度泛函理论计算表明，硫醇盐-芳基卤化物电子供体-受体复合物中可见光促进的分子间电荷转移允许在没有催化剂的情况下进行反应。
• PHOTOCATALYST-FREE, LIGHT-INDUCED CARBON-SULFUR CROSS-COUPLING METHODS
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE

  公开号：US20180370911A1

  公开（公告）日：2018-12-27

  In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.

  在某个方面，该发明提供了一种促进碳硫键形成反应的方法。在某些实施例中，该反应包括(hetero)aryl卤化物与硫醇的交叉偶联，形成碳硫键，其中该方法在没有光催化剂的情况下通过光照促进。在其他实施例中，交叉偶联反应可以通过可见光照射来促进，包括阳光。
• Deoxygenative C–S Bond Coupling with Sulfinates via Nickel/Photoredox Dual Catalysis
  作者：Shuai Zhong、Zhiwei Zhou、Feng Zhao、Guojiang Mao、Guo-Jun Deng、Huawen Huang

  DOI：10.1021/acs.orglett.2c00478

  日期：2022.3.11

  The C–S bond formation from aryl halides and thiols has been well established under various catalytic systems. In this work, user-friendly sulfinates have been exploited as an efficient sulfenylating reagent in the C–S couplings through visible-light-induced photo/nickel dual catalysis under base- and external reductant-free conditions. A large number of aryl sulfide products were accessed with high

  芳基卤化物和硫醇形成的 C-S 键已在各种催化体系下得到很好的证实。在这项工作中，在无碱和无外部还原剂的条件下，通过可见光诱导的光/镍双催化，用户友好的亚磺酸盐被用作 C-S 偶联中的有效亚磺酰化试剂。获得了大量芳基硫醚产品，具有高选择性和对各种功能的高耐受性。
• Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹
  作者：J. Scott Sawyer、Elisabeth A. Schmittling、Jayne A. Palkowitz、William J. Smith

  DOI：10.1021/jo980800g

  日期：1998.9.1

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.
• [EN] METHOD FOR SYNTHESISING DIARYL SULPHIDE COMPOUNDS IN A SOLID PHASE<br/>[FR] PROCEDE DE SYNTHESE EN PHASE SOLIDE DE COMPOSES DE TYPES SULFURES DE DIARYLE
  申请人：GALDERMA RES & DEV

  公开号：WO2005047237A1

  公开（公告）日：2005-05-26

  L'invention se rapporte à un procédé de synthèse en phase solide industrialisable de nouveaux composés de types sulfures de diaryle de formule générale (I). Elle se rapporte également à titre de produits industriels nouveaux et utiles, aux composés chimiques issus de cette synthèse, à des compositions pharmaceutiques ou dermatologiques les contenant et à leur utilisation dans des compositions pharmaceutiques destinées à un usage en médecine humaine ou vétérinaire, ou dans des compositions cosmétiques.