N-[(E)-2-phenylvinyl]azepane-2-thione | 1068465-02-0

• 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: N-[(E)-2-phenylvinyl]azepane-2-thione
• 英文别名: 1-[(E)-2-phenylethenyl]azepane-2-thione
• CAS: 1068465-02-0
• 化学式: C₁₄H₁₇NS
• 分子量: 231.362
• InChiKey: LLRSKKDERQWZTK-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  ε-硫代己内酰胺 、 苯乙炔 在 三辛基膦 、 bis(2-methallyl)(cycloocta-1,5-diene)ruthenium(II) 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以84%的产率得到N-[(E)-2-phenylvinyl]azepane-2-thione
  参考文献：
  名称：

  Ruthenium-Catalyzed Stereoselective anti-Markovnikov-Addition of Thioamides to Alkynes

  摘要：

  A catalyst system generated in situ from bis(2-methallyl)-cycloocta-1,5-diene-ruthenium(II) and a phosphine was found to efficiently catalyze the addition of thioamides to terminal alkynes with exclusive formation of the anti-Markovnikov thioenamide products. The stereoselectivity of the addition is usually high and controlled by the choice of the phosphine ligand, whereas the (E)-isomers are predominantly formed in the presence of tri(n-octyl)phosphine, the use of bis(dicyclohexylphosphino)methane preferentially leads to the formation of the (Z)-configured thioenamides.

  DOI：

  10.1021/ol801736h

文献信息

• Ruthenium-Catalyzed Stereoselective <i>anti</i>-Markovnikov-Addition of Thioamides to Alkynes
  作者：Lukas J. Goossen、Mathieu Blanchot、Kifah S. M. Salih、Ralf Karch、Andreas Rivas-Nass

  DOI：10.1021/ol801736h

  日期：2008.10.16

  A catalyst system generated in situ from bis(2-methallyl)-cycloocta-1,5-diene-ruthenium(II) and a phosphine was found to efficiently catalyze the addition of thioamides to terminal alkynes with exclusive formation of the anti-Markovnikov thioenamide products. The stereoselectivity of the addition is usually high and controlled by the choice of the phosphine ligand, whereas the (E)-isomers are predominantly formed in the presence of tri(n-octyl)phosphine, the use of bis(dicyclohexylphosphino)methane preferentially leads to the formation of the (Z)-configured thioenamides.