4-Acetoxy-2-(phenylthio)butanal | 59377-55-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-Acetoxy-2-(phenylthio)butanal
• 英文别名: (4-Oxo-3-phenylsulfanylbutyl) acetate；(4-oxo-3-phenylsulfanylbutyl) acetate
• CAS: 59377-55-8
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: BRKZUFJOZATMET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-丁炔-1-醋酸酯 、 苯硫酚 在 氧气 、 四乙基对甲苯磺酸铵 作用下， 以 溶剂黄146 为溶剂， 反应 6.5h， 以72%的产率得到4-Acetoxy-2-(phenylthio)butanal
  参考文献：
  名称：

  Electroinitiated oxygenation of alkenyl sulfides and alkynes in the presence of thiophenol

  摘要：

  Electrolysis of alkenyl sulfides in the presence of thiophenol with bubbling of molecular oxygen gave the corresponding alpha-(phenylthio) carbonyl compounds with the consumption of a catalytic amount of electricity. An electroinitiated radical chain mechanism has been proposed. The reaction also took place without electrochemical initiation, but much (5-50 times) longer reaction time was required for the completion of the reaction. The potential utility of the present reaction in organic synthesis is demonstrated by the net 1,2-transposition of a phenylthio group and a carbonyl group. The electroinitiated oxygenation of ketene dithioacetals also proceeded smoothly to give the corresponding alpha-(phenylthio) thiol esters. It was also found that the electroinitiated oxygenation of alkynes in the presence of thiophenol gave alpha-(phenylthio) carbonyl compounds. A mechanism involving the initial formation of alkenyl sulfides has been proposed.

  DOI：

  10.1021/jo00070a021

文献信息

• Preparation and reactions of 2-(alkoxy)-1-(alkyl or arylthio)vinyllithium. Application in the synthesis of 9-desoxo-9-thiaprostaglandins
  作者：Isidoros Vlattas、Laurence Della Vecchia、Avelina Ong Lee

  DOI：10.1021/ja00423a081

  日期：1976.3
• Electroinitiated oxygenation of alkenyl sulfides and alkynes in the presence of thiophenol
  作者：Junichi Yoshida、Shogo Nakatani、Sachihiko Isoe

  DOI：10.1021/jo00070a021

  日期：1993.8

  Electrolysis of alkenyl sulfides in the presence of thiophenol with bubbling of molecular oxygen gave the corresponding alpha-(phenylthio) carbonyl compounds with the consumption of a catalytic amount of electricity. An electroinitiated radical chain mechanism has been proposed. The reaction also took place without electrochemical initiation, but much (5-50 times) longer reaction time was required for the completion of the reaction. The potential utility of the present reaction in organic synthesis is demonstrated by the net 1,2-transposition of a phenylthio group and a carbonyl group. The electroinitiated oxygenation of ketene dithioacetals also proceeded smoothly to give the corresponding alpha-(phenylthio) thiol esters. It was also found that the electroinitiated oxygenation of alkynes in the presence of thiophenol gave alpha-(phenylthio) carbonyl compounds. A mechanism involving the initial formation of alkenyl sulfides has been proposed.