(3Z)-4-benzoyl-5-methylsulphanyl-3-[1-(phenyl)acetylidene]-3H-1,2-dithiole

• 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: (3Z)-4-benzoyl-5-methylsulphanyl-3-[1-(phenyl)acetylidene]-3H-1,2-dithiole
• 英文别名: (2Z)-2-(4-benzoyl-5-methylsulfanyldithiol-3-ylidene)-1-phenylethanone
• 化学式: C₁₉H₁₄O₂S₃
• 分子量: 370.517
• InChiKey: OGBRZXGPDBPQDN-VBKFSLOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 3-hydroxy-3-phenylprop-2-enedithioate 在 四(三苯基膦)钯 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以85%的产率得到(3Z)-4-benzoyl-5-methylsulphanyl-3-[1-(phenyl)acetylidene]-3H-1,2-dithiole
  参考文献：
  名称：

  Palladium Catalyzed Oxidative Coupling of α-Enolic Dithioesters: A New Entry to 3,4,5-Trisubstituted 1,2-Dithioles via a Double Activation Strategy

  摘要：

  An operationally simple, facile, and convenient one-pot straightforward method for the construction of 3,4,5-trisubstituted 1,2-dithioles has been explored and developed via palladium catalyzed self-coupling of alpha-enolic dithioesters for the first time. Pd(0) efficiently catalyzes the activation and cleavage of S-H and C-S bonds to achieve cascade coupling, which results in the concomitant formation of new S-S and C-C bonds. Optimization data, substrate scope, and mechanistic insights are discussed.

  DOI：

  10.1021/ol402728y

文献信息

• Palladium Catalyzed Oxidative Coupling of α-Enolic Dithioesters: A New Entry to 3,4,5-Trisubstituted 1,2-Dithioles <i>via</i> a Double Activation Strategy
  作者：Sushobhan Chowdhury、Tanmoy Chanda、Suvajit Koley、B. Janaki Ramulu、Raymond C. F. Jones、Maya Shankar Singh

  DOI：10.1021/ol402728y

  日期：2013.10.18

  An operationally simple, facile, and convenient one-pot straightforward method for the construction of 3,4,5-trisubstituted 1,2-dithioles has been explored and developed via palladium catalyzed self-coupling of alpha-enolic dithioesters for the first time. Pd(0) efficiently catalyzes the activation and cleavage of S-H and C-S bonds to achieve cascade coupling, which results in the concomitant formation of new S-S and C-C bonds. Optimization data, substrate scope, and mechanistic insights are discussed.