Bis-methylsulfanyl-naphthalen-2-yl-thioacetic acid S-methyl ester | 195305-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Bis-methylsulfanyl-naphthalen-2-yl-thioacetic acid S-methyl ester
• 英文别名: S-methyl 2,2-bis(methylsulfanyl)-2-naphthalen-2-ylethanethioate
• CAS: 195305-66-9
• 化学式: C₁₅H₁₆OS₃
• 分子量: 308.489
• InChiKey: IODBNTMULUDAGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  Bis-methylsulfanyl-naphthalen-2-yl-thioacetic acid S-methyl ester 在 氢氧化钾 、 potassium tert-butylate 、 mesna 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 3.67h， 生成 (+-)-2-[2]naphthyl-propionic acid
  参考文献：
  名称：

  S-烷基（芳基）双（烷基硫烷基）硫代乙酸酯的有趣合成应用：制备（±）-α-芳基丙酸的一般程序

  摘要：

  本文报道了一种合成外消旋形式的 α-芳基丙酸 1 的新方法，从芳族羧酸 2（即酯）的衍生物开始，通过 1-芳基-2,2,2-三（烷基硫烷基）乙酮4-6，S-烷基（芳基）双（烷基硫基）硫代乙酸酯 7-9，S-烷基 α-芳基-α-（烷基硫烷基）硫代丙酸酯 10-12 和 S-烷基 α-芳基硫代丙酸酯 13-15。每个阶段都很容易发生，并且产量总是很高。

  DOI：

  10.1055/s-2002-28521
• 作为产物：
  描述：

  2,2,2-Tris-methylsulfanyl-1-naphthalen-2-yl-ethanone 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到Bis-methylsulfanyl-naphthalen-2-yl-thioacetic 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+

文献信息

• 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.
• An Interesting Synthetic Application of S-Alkyl (Aryl)bis(alkylsulfanyl)thioacetates: General Procedure for the Preparation of (±)-α-Arylpropionic Acids
  作者：Marco Clericuzio、Iacopo Degani、Stefano Dughera、Rita Fochi

  DOI：10.1055/s-2002-28521

  日期：——

  Reported here is a new procedure for the synthesis of α-arylpropionic acids 1 in the racemic form, starting from derivatives of aromatic carboxylic acids 2 (i.e., esters), via 1-aryl-2,2,2-tris(alkylsulfanyl)ethanones 4-6, S-alkyl (aryl)bis(alkylsulfanyl)thioacetates 7-9, S-alkyl α-aryl-α-(alkylsulfanyl)thiopropionates 10-12 and S-alkyl α-arylthiopropionates 13-15. Each stage takes place easily and

  本文报道了一种合成外消旋形式的 α-芳基丙酸 1 的新方法，从芳族羧酸 2（即酯）的衍生物开始，通过 1-芳基-2,2,2-三（烷基硫烷基）乙酮4-6，S-烷基（芳基）双（烷基硫基）硫代乙酸酯 7-9，S-烷基 α-芳基-α-（烷基硫烷基）硫代丙酸酯 10-12 和 S-烷基 α-芳基硫代丙酸酯 13-15。每个阶段都很容易发生，并且产量总是很高。