1-[1-(Benzenesulfonyl)pyrrol-2-yl]-2,2,2-tris(methylsulfanyl)ethanone | 171897-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[1-(Benzenesulfonyl)pyrrol-2-yl]-2,2,2-tris(methylsulfanyl)ethanone
• CAS: 171897-81-7
• 化学式: C₁₅H₁₇NO₃S₄
• 分子量: 387.569
• InChiKey: SWMTUCVINZVJNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[1-(Benzenesulfonyl)pyrrol-2-yl]-2,2,2-tris(methylsulfanyl)ethanone 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以52%的产率得到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
• 作为产物：
  描述：

  2-吡咯甲酸甲酯 在 sodium hydroxide 、 正丁基锂 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-[1-(Benzenesulfonyl)pyrrol-2-yl]-2,2,2-tris(methylsulfanyl)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

• 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.