S-methyl bis(methylsulfanyl)thioacetate | 101010-60-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: S-methyl bis(methylsulfanyl)thioacetate
• 英文别名: S-Methyl bis(methylsulfanyl)ethanethioate；S-methyl 2,2-bis(methylsulfanyl)ethanethioate
• CAS: 101010-60-0
• 化学式: C₅H₁₀OS₃
• 分子量: 182.332
• InChiKey: LUDXMWZQWDRUQB-UHFFFAOYSA-N

物化性质

• 沸点：
  237.5±30.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  93
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Tris-(methylmercapto)-acetaldehyd 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到S-methyl bis(methylsulfanyl)thioacetate
  参考文献：
  名称：

  Isomerization of Trimethyl α-Keto Trithioorthocarboxylates into α,α-Bis(methylthio) Thiolcarboxylates. A New Rearrangement of Synthetic Interest

  摘要：

  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.

  DOI：

  10.1021/jo970683+

文献信息

• On the thermal Pummerer rearrangement of substituted sulfoxides
  作者：Liliana Marzorati、Eduardo K.C. Yoshikawa、Ataualpa A.C. Braga、Claudio Di Vitta

  DOI：10.1080/17415993.2013.853066

  日期：2014.5.4

  Sulfoxides bearing thioester and ester groups at the α position under heating at ca. 140°C undergo Pummerer thermal rearrangement. However, for sulfonyl sulfoxide, a complex mixture of products is formed. Plausible mechanism is advanced. GRAPHICAL ABSTRACT

  在 α 位带有硫酯和酯基团的亚砜在约 10 ℃加热。140°C进行Pummerer热重排。然而，对于磺酰亚砜，会形成复杂的产物混合物。合理的机制是先进的。图形概要
• Halogenated epoxides. 9. Reaction of trans-2,3-dichlorooxirane with dimethyl sulfide
  作者：Karl Griesbaum、Pallikaparampil M. Scaria、Thomas Doehling

  DOI：10.1021/jo00358a026

  日期：1986.4
• Barbero, Margherita; Cadamuro, Silvano; Degani, Iacopo, Journal of the Chemical Society. Perkin transactions I, 1993, # 17, p. 2075 - 2080
  作者：Barbero, Margherita、Cadamuro, Silvano、Degani, Iacopo、Dughera, Stefano、Fochi, Rita

  DOI：——

  日期：——
• GRIESBAUM, K.;SCARIA, P. M.;DOEHLING, T., J. ORG. CHEM., 1986, 51, N 8, 1302-1305
  作者：GRIESBAUM, K.、SCARIA, P. M.、DOEHLING, T.

  DOI：——

  日期：——
• 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.