1-(2-(p-tolylthio)phenyl)ethan-1-one | 52252-60-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(p-tolylthio)phenyl)ethan-1-one
• 英文别名: 1-[2-(4-Methylphenyl)sulfanylphenyl]ethanone
• CAS: 52252-60-5
• 化学式: C₁₅H₁₄OS
• mdl: MFCD11115586
• 分子量: 242.342
• InChiKey: WPWKEIVKMZLYTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-(p-tolylthio)phenyl)ethan-1-one 在 lithium aluminium tetrahydride 作用下， 生成 Methyl-o-(p-tolylthio)phenylcarbinol
  参考文献：
  名称：

  邻芳基硫代苯基取代的甲醇被酸催化环化为噻吨酮衍生物时的1,2-硫转移

  摘要：

  在一些邻-芳基硫基苯基取代的甲醇的酸催化环化为噻吨酮衍生物的过程中，观察到芳基硫基中具有对甲基取代基的甲醇的排列。因此，1- [邻-（对甲苯硫基）苯基]乙醇给出了3,9-二甲基噻吨，而α-[邻-（对甲苯硫基）苯基]苄醇得到了3-甲基-和2-甲基-的混合物。 9-苯基噻吨。环化的机理在位置闭环之间的竞争方面所讨论的邻位的硫（邻闭环3'-取代），并且在位置带有硫接着是1,2-硫移（ipso -substitution）。

  DOI：

  10.1039/p19730002250
• 作为产物：
  描述：

  邻硝基苯乙酮 、 4-甲苯硫酚 在 potassium phosphate 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以33%的产率得到1-(2-(p-tolylthio)phenyl)ethan-1-one
  参考文献：
  名称：

  C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

  摘要：

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.07.012

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。
• UEDA I.; SATO Y.; MAENO S.; UMIO S., CHEM. AND PHARM. BULL. <CPBT-AL>, 1975, 23, NO 10, 2223-2231,
  作者：UEDA I.、 SATO Y.、 MAENO S.、 UMIO S.

  DOI：——

  日期：——
• C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
  作者：Maojie Xuan、Chunlei Lu、Bo-Lin Lin

  DOI：10.1016/j.cclet.2019.07.012

  日期：2020.1

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• 1,2-Sulphur shift in the acid-catalysed cyclisation of o-arylthiophenyl-substituted carbinols to thioxanthen derivatives
  作者：Giuseppe Capozzi、Giovanni Melloni、Giorgio Modena

  DOI：10.1039/p19730002250

  日期：——

  During the acid-catalysed cyclisation of some o-arylthiophenyl-substituted carbinols to thioxanthen derivatives, arearrangement was observed with carbinols having a para-methyl substituentin thearylthio-group. Thus, 1-[o-(p-tolylthio)phenyl]ethanol gave 3,9-dimethylthioxanthen, while α-[o-(p-tolylthio)phenyl]benzyl alcohol gave a mixture of 3-methyl- and 2-methyl-9-phenylthioxanthen. The mechanism

  在一些邻-芳基硫基苯基取代的甲醇的酸催化环化为噻吨酮衍生物的过程中，观察到芳基硫基中具有对甲基取代基的甲醇的排列。因此，1- [邻-（对甲苯硫基）苯基]乙醇给出了3,9-二甲基噻吨，而α-[邻-（对甲苯硫基）苯基]苄醇得到了3-甲基-和2-甲基-的混合物。 9-苯基噻吨。环化的机理在位置闭环之间的竞争方面所讨论的邻位的硫（邻闭环3'-取代），并且在位置带有硫接着是1,2-硫移（ipso -substitution）。