6-phenylhex-3-ene-1,5-diyn-3-yl phenyl sulfide | 1176910-98-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-phenylhex-3-ene-1,5-diyn-3-yl phenyl sulfide
• 英文别名: [(E)-6-phenylhex-3-en-1,5-diyn-3-yl]sulfanylbenzene
• CAS: 1176910-98-7
• 化学式: C₁₈H₁₂S
• 分子量: 260.359
• InChiKey: UTTDAQXQBPPHFE-BMRADRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (3R,4S)-1-phenyl-4-phenylsulfanylhexa-1,5-diyn-3-ol 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以83%的产率得到6-phenylhex-3-ene-1,5-diyn-3-yl phenyl sulfide
  参考文献：
  名称：

  Use ofN-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water

  摘要：

  Indium-promoted coupling reactions between propargyl aldehydes (1) and alpha-chloropropargylphenyl sulfide are reported. Although water has been shown to accelerate indium metal promoted reactions, the reverse pattern was observed in this series. Use of N-methylformamide (NMF), which has riot previously been a solvent known for use in indium-promoted reactions, afforded ail acceleration or these Barbier-style reactions compared to water. Indium-promoted reactions in this study also showed excellent regiocontrol and good stereocontrol, allowing for easy entry into the formation of epoxydiyne and enediyne skeletal structures, This paper also describes use of the Barbier Coupled product (2) as a new, and easy, entry into the formation of enediyne and epoxydiyne skeletal structures.

  DOI：

  10.1021/jo900763u