2,2,2-Tris(methylsulfanyl)-1-phenylethanone | 21504-18-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Tris(methylsulfanyl)-1-phenylethanone
• CAS: 21504-18-7
• 化学式: C₁₁H₁₄OS₃
• 分子量: 258.43
• InChiKey: OUASNJIDTSXGKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-Tris(methylsulfanyl)-1-phenylethanone 在 tetrafluoroboric acid 、 mercury(II) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以100%的产率得到S-methyl 2-oxo-2-phenylethanethioate
  参考文献：
  名称：

  A Simple and High Yield General Route to Methyl α-Oxo Thiolcarboxylates

  摘要：

  甲基-β-氧代硫羧酸酯（脂肪族、芳香族和杂芳族）可通过在THF水溶液中用N-溴代琥珀酰亚胺或用HgO/35% HBF4水溶液水解相应的三甲基-β-氧代三硫代邻酯，获得良好至极佳的收率。

  DOI：

  10.1055/s-1996-4234
• 作为产物：
  描述：

  2-甲基亚磺酰-1-苯乙酮 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 2,2,2-Tris(methylsulfanyl)-1-phenylethanone
  参考文献：
  名称：

  Novel uncatalyzed thermal Pummerer rearrangements

  摘要：

  DOI：

  10.1021/jo00074a051

文献信息

• Synthesis of trimethyl .alpha.-keto trithioorthoesters and dimethyl .alpha.-keto dithioacetals by reaction of esters with tris(methylthio)methyllithium
  作者：Margherita Barbero、SIlvano Cadamuro、Iacopo Degani、Stefano Dughera、Rita Fochi

  DOI：10.1021/jo00124a009

  日期：1995.9

  A complete study has been made of the reaction of tris(methylthio)methyllithium with aromatic, heteroaromatic, and aliphatic esters. It is a one-pot reaction that despite its complexity, and depending on the reagent ratios, the reaction conditions, and the possible use of additional reagents (N-(methylthio)phthalimide or BuLi), can supply easily, in excellent and reproducible yields, the trimethyl alpha-keto trithioorthoesters 3 or, alternatively, the dimethyl a-keto dithioacetals 4. The reaction mechanism has been elucidated.
• Isomerization of Trimethyl α-Keto Trithioorthocarboxylates into α,α-Bis(methylthio) Thiolcarboxylates. A New Rearrangement of Synthetic Interest
  作者：Iacopo Degani、Stefano Dughera、Rita Fochi、Sonia Gazzetto

  DOI：10.1021/jo970683+

  日期：1997.10.1

  A study was made of the isomerization reaction of a great variety of trimethyl alpha-keto trithioorthocarboxylates to alpha,alpha-bis(methylthio) thiolcarboxylates, intermediates of high synthetic value for the synthesis of alpha-arylpropionic acids. The reaction was carried out In methylene chloride in the presence of catalytic amounts of trityl perchlorate or methanesulfonic acid and was complete in 2 h at rt. In most of the investigated cases the result was positive, the yields usually being greater than 90%. Also the reaction mechanism was subjected to an experimental study.
• Synthesis of Trimethyl α-Keto Trithioorthoesters and Dimethyl α-Keto Dithioacetals by Reaction of Acyl Chlorides, Anhydrides, Thiol Esters, and <i>N</i>,<i>N</i>-Dimethylamides with [Tris(methylthio)methyl]lithium
  作者：Iacopo Degani、Stefano Dughera、Rita Fochi、Emanuela Serra

  DOI：10.1021/jo961194x

  日期：1996.1.1
• Novel uncatalyzed thermal Pummerer rearrangements
  作者：B. Wladislaw、L. Marzorati、F. C. Biaggio

  DOI：10.1021/jo00074a051

  日期：1993.10
• A Simple and High Yield General Route to Methyl α-Oxo Thiolcarboxylates
  作者：Iacopo Degani、Stefano Dughera、Rita Fochi、Antonella Gatti

  DOI：10.1055/s-1996-4234

  日期：1996.4

  Methyl α-oxo thiolcarboxylates (aliphatic, aromatic and heteroaromatic) are obtained in good to excellent yields by hydrolysis of the corresponding trimethyl α-oxo trithioorthoesters with N-bromosuccinimide in aqueous THF or with HgO/35% aqueous HBF4 ves.

  甲基-β-氧代硫羧酸酯（脂肪族、芳香族和杂芳族）可通过在THF水溶液中用N-溴代琥珀酰亚胺或用HgO/35% HBF4水溶液水解相应的三甲基-β-氧代三硫代邻酯，获得良好至极佳的收率。