1-[4-(2-Methylpropyl)phenyl]-2,2,2-tris(methylsulfanyl)ethanone | 185101-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(2-Methylpropyl)phenyl]-2,2,2-tris(methylsulfanyl)ethanone
• CAS: 185101-76-2
• 化学式: C₁₅H₂₂OS₃
• 分子量: 314.537
• InChiKey: MAWZGKJHPOTTCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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-[4-(2-Methylpropyl)phenyl]-2,2,2-tris(methylsulfanyl)ethanone 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到S-methyl 2-[4-(2-methylpropyl)phenyl]-2,2-bis(methylsulfanyl)ethanethioate
  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：

  4-(2-甲基丙基)苯甲酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1-[4-(2-Methylpropyl)phenyl]-2,2,2-tris(methylsulfanyl)ethanone
  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

• 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
• 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.