1,1,1-Tris(methylsulfanyl)undecan-2-one | 171897-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1-Tris(methylsulfanyl)undecan-2-one
• CAS: 171897-83-9
• 化学式: C₁₄H₂₈OS₃
• 分子量: 308.574
• InChiKey: HISVWOHHHLXBQC-UHFFFAOYSA-N

物化性质

• 沸点：
  378.4±42.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  1,1,1-Tris(methylsulfanyl)undecan-2-one 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到2,2-Bis-methylsulfanyl-undecanethioic acid S-methyl ester
  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+
• 作为产物：
  描述：

  S-ethyl decanethioate 在 正丁基锂 、 N-(乙基硫代)邻苯二甲酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1,1,1-Tris(methylsulfanyl)undecan-2-one
  参考文献：
  名称：

  Synthesis of Trimethyl α-Keto Trithioorthoesters and Dimethyl α-Keto Dithioacetals by Reaction of Acyl Chlorides, Anhydrides, Thiol Esters, and N,N-Dimethylamides with [Tris(methylthio)methyl]lithium

  摘要：

  DOI：

  10.1021/jo961194x

文献信息

• 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。
• 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