S-phenyl 2,2-dimethylpropanethioate | 60718-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl 2,2-dimethylpropanethioate
• 英文别名: Propanethioic acid, 2,2-dimethyl-, S-phenyl ester
• CAS: 60718-19-6
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: QJVAIUXDOWXXCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  S-phenyl 2,2-dimethylpropanethioate 在 clay supported ammonium nitrate "Clayan" 作用下， 反应 0.07h， 以95%的产率得到二苯二硫醚
  参考文献：
  名称：

  Microwave Thermolysis VII: Oxidative Coupling of Thiol Acetates and Esters Using “Clayan” in Dry Media

  摘要：

  Disulfide bond formation by the oxidative cleavage of thiol acetates and thiol esters using "Clayan" under microwave irradiation is described. The non-metallic and inexpensive nature of the reagent are the important features of the procedure.

  DOI：

  10.1080/00397919908086432
• 作为产物：
  描述：

  三甲基乙酸 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 S-phenyl 2,2-dimethylpropanethioate
  参考文献：
  名称：

  Synthesis of Thiol Esters by Carboxylic Trichlorobenzoic Anhydrides

  摘要：

  通过将2,4,6-三氯苯甲酰氯和羧酸制备的混合酸酐与各种类型的硫醇在4-二甲氨基吡啶存在下进行处理，快速且高收率地获得了硫代羧酸S-酯。

  DOI：

  10.1246/bcsj.54.943

文献信息

• Activation of mixed carboxylic α-bromotoluoyl anhydrides by silver tetraflouroborate. Synthesis of ester and thiol esters
  作者：Satoshi Fukuoka、Seiji Takimoto、Tsutomu Katsuki、Masaru Yamaguchi

  DOI：10.1016/s0040-4039(00)96605-x

  日期：1987.1

  Mixed carboxylic α-bromotoluoyl anhydrides were activated by silver tetrafluoroborate through intramolecular cyclization and reacted with alcohols or thiols giving the corresponding esters or thiol esters in good yileds with the elimination of phthalide.

  四氟硼酸银通过分子内环化作用活化了混合的羧酸α-溴代甲酰酐酸酐，并与醇或硫醇反应生成了相应的酯或硫醇酯，从而获得了良好的产率，并且消除了邻苯二甲酰胺。
• Radical reaction of S-phenyl chlorothioformate with alkyl iodides: free radical-mediated carboxylation approach
  作者：Sunggak Kim

  DOI：10.1039/a800664d

  日期：——

  Free radical-mediated carboxylation is achieved by treatment of alkyl iodides with S-phenyl chlorothioformate and bis(tributyltin) with irradiation at 300 nm.

  通过在300 nm波长照射下，使用S-苯基氯硫代甲酸酯和双(三丁基锡)处理烷基碘化物，实现了自由基介导的羧化反应。
• Manganese(<scp>iii</scp>)-promoted thiocarbonylation of alkylborates with disulfides: synthesis of aliphatic thioesters
  作者：Bo Chen、Xiao-Feng Wu

  DOI：10.1039/d1ob01960k

  日期：——

  A Mn(III)-promoted thiocarbonylation procedure toward the synthesis of thioesters has been developed. By employing easily available disulfides and potassium alkyltrifluoroborates as the starting materials, and cheap and non-toxic Mn(OAc)3·2H2O as the promotor, a broad range of thioesters were synthesized in good to excellent yields via radical intermediates.

  已开发出一种用于合成硫酯的 Mn( III ) 促进的硫代羰基化过程。以易得的二硫化物和烷基三氟硼酸钾为起始原料，以廉价且无毒的Mn(OAc) 3 ·2H 2 O为促进剂，通过自由基中间体以良好至优异的产率合成了多种硫酯。
• S-Acylation of aliphatic and aromatic thiols with carboxylic acids and their esters over solid acid catalysts in the gas phase at temperatures above 200°C
  作者：Sayoko Nagashima、Hitomi Yamazaki、Kentaro Kudo、Satoshi Kamiguchi、Teiji Chihara

  DOI：10.1016/j.apcata.2013.06.011

  日期：2013.8

  Benzenethiol is reacted with acetic acid in a hydrogen stream over [(Mo6Cl8)Cl4(H2O)2]·6H2O. Catalytic activity of the clusters appears above 200 °C, yielding S-phenyl thioacetate. The selectivity is 98% at 300 °C. Niobium, tantalum, and tungsten halide clusters with the same octahedral metal framework also catalyze the reaction. Benzoic acid and aliphatic carboxylic acids afford the corresponding S-phenyl

  苯硫醇用乙酸在氢气流中在[（反应的Mo 6氯8）氯4（H 2 O）2 ]·6H 2 O.催化簇出现在200℃以上的活性，得到小号-苯基硫代乙酸酯。在300°C下的选择性为98％。具有相同八面体金属骨架的铌，钽和卤化钨簇也催化该反应。苯甲酸和脂族羧酸通过与苯硫醇反应得到相应的S-苯基碳硫盐。脂肪族硫醇也被S-酰化以产生相应的S-烷基硫代碳酸盐。当羧酸酯与苯硫醇在[（Nb 6 Cl 12）Cl 2（H 2 O）4 ]·4H 2 O上于450°C应用于反应时，该酯的空间不受阻碍的部分被并入产物中：S选择性地获得-苯基硫代乙酸酯或甲基苯基硫。通过热活化在簇状配合物上形成的布朗斯台德酸位点是催化剂的活性位点。因此，在200°C以上稳定的固体酸（例如二氧化硅-氧化铝，沸石和杂多酸）也会催化这些反应。
• A New and Efficient Esterification Reaction via Mixed Anhydrides by the Promotion of a Catalytic Amount of Lewis Acid
  作者：Mitsutomo Miyashita、Isamu Shiina、So Miyoshi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.66.1516

  日期：1993.5

  In the presence of a catalytic amount of Lewis acid, various carboxylic esters or S-phenyl carbothioates are prepared in excellent yields by the respective reactions of equimolar amounts of silyl carboxylates and alkyl silyl ethers or phenyl silyl sulfides with 4-trifluoromethylbenzoic anhydride.

  在催化量的路易斯酸存在下，通过等摩尔量的甲硅烷基羧酸酯和烷基甲硅烷基醚或苯基甲硅烷基硫化物与4-三氟甲基苯甲酸酐的相应反应，以极好的收率制备各种羧酸酯或S-苯基硫代碳酸酯。