2,2,2-tris(methylsulfanyl)-1-(1H-pyrrol-2-yl)ethanone | 171897-80-6

• 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-(1H-pyrrol-2-yl)ethanone
• CAS: 171897-80-6
• 化学式: C₉H₁₃NOS₃
• 分子量: 247.406
• InChiKey: QYJPWFAWKSTZQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-tris(methylsulfanyl)-1-(1H-pyrrol-2-yl)ethanone 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以94%的产率得到Oxo-(1H-pyrrol-2-yl)-thioacetic acid S-methyl ester
  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-吡咯甲酸甲酯 在 氢氧化钾 、 sodium hydroxide 、 正丁基锂 、 四丁基硫酸氢铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2,2,2-tris(methylsulfanyl)-1-(1H-pyrrol-2-yl)ethanone
  参考文献：
  名称：

  Synthesis of trimethyl .alpha.-keto trithioorthoesters and dimethyl .alpha.-keto dithioacetals by reaction of esters with tris(methylthio)methyllithium

  摘要：

  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.

  DOI：

  10.1021/jo00124a009

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.
• 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。