(Z)-1-(2-(2-(methylthio)-2-phenylvinyl)phenyl)ethanone | 1359978-78-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-1-(2-(2-(methylthio)-2-phenylvinyl)phenyl)ethanone
• 英文别名: 1-[2-[(Z)-2-methylsulfanyl-2-phenylethenyl]phenyl]ethanone
• CAS: 1359978-78-1
• 化学式: C₁₇H₁₆OS
• 分子量: 268.379
• InChiKey: GOTLKODCAYRNBQ-ATVHPVEESA-N

物化性质

• 沸点：
  420.9±45.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-(2-(2-(methylthio)-2-phenylvinyl)phenyl)ethanone 在 ammonium acetate 、 溶剂黄146 作用下， 反应 16.0h， 以30 mg的产率得到1-甲基-3-苯基异喹啉
  参考文献：
  名称：

  Activating Group Recycling in Action: A Rhodium-Catalyzed Carbothiolation Route to Substituted Isoquinolines

  摘要：

  A new rhodium(l) catalyst allows practical and efficient alkyne carbothiolation reactions to be achieved on synthetically useful ketone-bearing aryl methyl sulfides. The carbothiolation adducts, featuring a 'recycled methyl sulfide' activating group, are convenient precursors to highly substituted isoquinolines.

  DOI：

  10.1021/ol402650q
• 作为产物：
  描述：

  1-[2-(甲基硫代)苯基]乙酮 、 苯乙炔 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以39 mg的产率得到(Z)-1-(2-(2-(methylthio)-2-phenylvinyl)phenyl)ethanone
  参考文献：
  名称：

  Activating Group Recycling in Action: A Rhodium-Catalyzed Carbothiolation Route to Substituted Isoquinolines

  摘要：

  A new rhodium(l) catalyst allows practical and efficient alkyne carbothiolation reactions to be achieved on synthetically useful ketone-bearing aryl methyl sulfides. The carbothiolation adducts, featuring a 'recycled methyl sulfide' activating group, are convenient precursors to highly substituted isoquinolines.

  DOI：

  10.1021/ol402650q

文献信息

• Aryl Methyl Sulfides as Substrates for Rhodium-Catalyzed Alkyne Carbothiolation: Arene Functionalization with Activating Group Recycling
  作者：Joel F. Hooper、Adrian B. Chaplin、Carlos González-Rodríguez、Amber L. Thompson、Andrew S. Weller、Michael C. Willis

  DOI：10.1021/ja2108992

  日期：2012.2.15

  A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the products as an alkenyl sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process.
• Activating Group Recycling in Action: A Rhodium-Catalyzed Carbothiolation Route to Substituted Isoquinolines
  作者：Milan Arambasic、Joel F. Hooper、Michael C. Willis

  DOI：10.1021/ol402650q

  日期：2013.10.18

  A new rhodium(l) catalyst allows practical and efficient alkyne carbothiolation reactions to be achieved on synthetically useful ketone-bearing aryl methyl sulfides. The carbothiolation adducts, featuring a 'recycled methyl sulfide' activating group, are convenient precursors to highly substituted isoquinolines.