ethyl(4-(methylsulfonyl)phenyl)sulfane

• 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: ethyl(4-(methylsulfonyl)phenyl)sulfane
• 英文别名: 1-Ethylsulfanyl-4-methylsulfonylbenzene
• 化学式: C₉H₁₂O₂S₂
• 分子量: 216.325
• InChiKey: ITSFCYXMHRNNJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl(4-(methylsulfonyl)phenyl)sulfane 在 三乙基硅烷 、 三甲基氯硅烷 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以98%的产率得到苯甲砜
  参考文献：
  名称：

  Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride

  摘要：

  The palladium-catalyzed reductive cleavage of alkyl aryl sulfides to afford the corresponding arenes in high yield, which is both accelerated and exhibits increased functional group selectivity in the presence of TMSCI, is described. This ligand-free reaction features mild conditions, easy operation, use of readily available reagents, and high functional group selectivity. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.002
• 作为产物：
  描述：

  1,4-二氯苯 在 四丁基溴化铵 、 甲基锂 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 四氢呋喃 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 24.0h， 生成 ethyl(4-(methylsulfonyl)phenyl)sulfane
  参考文献：
  名称：

  A New Reaction of 2-(Phenylsulfonyl)-3-phenyloxaziridine (Davis Reagent):  Oxidation of Thiolates to Sulfinates. Application to the Synthesis of Sulfones

  摘要：

  [GRAPHICS]The first efficient and general method for the generation of sulfinate anions by oxidation of the corresponding thiolates is described. The oxidizing agent employed is the classical 2-(phenylsulfonyl)-3-phenyloxaziridine, commonly known as the Davis reagent. Subsequent Salkylation of the sulfinates under phase-transfer catalysis affords sulfones 6 in 71-91% isolated yields (10 examples).

  DOI：

  10.1021/ol990170k

文献信息

• Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
  作者：Tristan Delcaillau、Philip Boehm、Bill Morandi

  DOI：10.1021/jacs.1c00529

  日期：2021.3.17

  We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications

  我们描述了芳基腈和芳基硫醚之间的新官能团复分解。催化系统镍/dcype 对于实现这种完全可逆的转化，以良好的收率至关重要。此外，不含氰化物和硫醇的反应显示出高官能团耐受性和商业分子后期衍生化的高效率。最后，合成应用证明了它在多步合成中的多功能性和实用性。
• A mild and efficient new synthesis of aryl sulfones from boronic acids and sulfinic acid salts
  作者：Christian Beaulieu、Daniel Guay、Zhaoyin Wang、David A. Evans

  DOI：10.1016/j.tetlet.2004.02.127

  日期：2004.4

  A new efficient and mild preparation of sulfones from boronic acids and sulfinic acid salts is reported. The cross-coupling reaction mediated by cupric acetate gives access to a variety of sulfones in excellent yield.

  据报道，一种新的由硼酸和亚磺酸盐有效，温和地制备砜的方法。由乙酸铜介导的交叉偶联反应以优异的产率获得了多种砜。
• A General Copper-Catalyzed Sulfonylation of Arylboronic Acids
  作者：Anirban Kar、Iliyas Ali Sayyed、Wei Fun Lo、Hanns Martin Kaiser、Matthias Beller、Man Kin Tse

  DOI：10.1021/ol071396n

  日期：2007.8.1

  A general copper-catalyzed method for the sulfonylation of arylboronic acids with sulfinate salts is described. A variety of alkyl-aryl, diaryl, and alkyl-heteroaryl sulfones were synthesized in good yield.
• Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride
  作者：Takehiko Matsumura、Takashi Niwa、Masahisa Nakada

  DOI：10.1016/j.tetlet.2012.06.002

  日期：2012.8

  The palladium-catalyzed reductive cleavage of alkyl aryl sulfides to afford the corresponding arenes in high yield, which is both accelerated and exhibits increased functional group selectivity in the presence of TMSCI, is described. This ligand-free reaction features mild conditions, easy operation, use of readily available reagents, and high functional group selectivity. (c) 2012 Elsevier Ltd. All rights reserved.
• A New Reaction of 2-(Phenylsulfonyl)-3-phenyloxaziridine (Davis Reagent):  Oxidation of Thiolates to Sulfinates. Application to the Synthesis of Sulfones
  作者：Franck Sandrinelli、Stéphane Perrio、Pierre Beslin

  DOI：10.1021/ol990170k

  日期：1999.10.1

  [GRAPHICS]The first efficient and general method for the generation of sulfinate anions by oxidation of the corresponding thiolates is described. The oxidizing agent employed is the classical 2-(phenylsulfonyl)-3-phenyloxaziridine, commonly known as the Davis reagent. Subsequent Salkylation of the sulfinates under phase-transfer catalysis affords sulfones 6 in 71-91% isolated yields (10 examples).