(E)-1-(2-((Z)-2-(methylthio)-2-phenylvinyl)-5-(trifluoromethyl)phenyl)non-2-en-1-one | 1359978-87-2

• 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: (E)-1-(2-((Z)-2-(methylthio)-2-phenylvinyl)-5-(trifluoromethyl)phenyl)non-2-en-1-one
• 英文别名: (E)-1-[2-[(Z)-2-methylsulfanyl-2-phenylethenyl]-5-(trifluoromethyl)phenyl]non-2-en-1-one
• CAS: 1359978-87-2
• 化学式: C₂₅H₂₇F₃OS
• 分子量: 432.55
• InChiKey: FJOMEGWVQZJVNW-YUSBXDGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-辛炔 、 2-(methylthio)-5-(trifluoromethyl)benzaldehyde 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 [Rh(κ2P,P-DPEphos)(ν6-o-xylene)][BArF4] 、 氢气 、 双(二环己基膦)甲烷 作用下， 以 邻二甲苯 、 丙酮 为溶剂， 反应 7.0h， 生成 (E)-1-(2-((Z)-2-(methylthio)-2-phenylvinyl)-5-(trifluoromethyl)phenyl)non-2-en-1-one
  参考文献：
  名称：

  Aryl Methyl Sulfides as Substrates for Rhodium-Catalyzed Alkyne Carbothiolation: Arene Functionalization with Activating Group Recycling

  摘要：

  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.

  DOI：

  10.1021/ja2108992

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.