1-phenylsulphenyl-1,4-pentadiene

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-phenylsulphenyl-1,4-pentadiene
• 英文别名: Penta-1,4-dienylsulfanylbenzene；penta-1,4-dienylsulfanylbenzene
• 化学式: C₁₁H₁₂S
• 分子量: 176.282
• InChiKey: PGOPXUVSHRQFLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenylsulphenyl-1,4-pentadiene 在 正丁基锂 、 氘代甲醇-d 作用下， 生成 (E)-1-phenylsulphenyl-1-deutero-2,4-pentadiene
  参考文献：
  名称：

  Regio- and stereo-chemistry of the coupling reaction of phenylsulphenyl-, phenylsulphinyl- and phenylsulphonyl-pentadienyl metals

  摘要：

  The coupling reaction of phenylsulphenyl-, phenylsulphinyl- and phenylsulphonyl-pentadienyl metals 3a-g has been studied showing that while 3c-g couple in any case regioselectively and stereoselectively, the coupling of 3a-b is counteraction and electrophile dependent. The alpha-regioisomeric coupling products of phenylsulphenylpentadienyl metals may undergo [1,5] sigmatropic rearrangement, those of phenylsulphinyl- and phenylsulphonyl-pentadienyl metals give fast double [3,2] sigmatropic isomerization.

  DOI：

  10.1016/s0040-4020(01)89751-9
• 作为产物：
  描述：

  (Z)-1-bromo-2-phenylthioethene 、 烯丙基溴化镁 在 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以87%的产率得到1-phenylsulphenyl-1,4-pentadiene
  参考文献：
  名称：

  Regio- and stereo-chemistry of the coupling reaction of phenylsulphenyl-, phenylsulphinyl- and phenylsulphonyl-pentadienyl metals

  摘要：

  The coupling reaction of phenylsulphenyl-, phenylsulphinyl- and phenylsulphonyl-pentadienyl metals 3a-g has been studied showing that while 3c-g couple in any case regioselectively and stereoselectively, the coupling of 3a-b is counteraction and electrophile dependent. The alpha-regioisomeric coupling products of phenylsulphenylpentadienyl metals may undergo [1,5] sigmatropic rearrangement, those of phenylsulphinyl- and phenylsulphonyl-pentadienyl metals give fast double [3,2] sigmatropic isomerization.

  DOI：

  10.1016/s0040-4020(01)89751-9

文献信息

• Regio- and stereo-chemistry of the coupling reaction of phenylsulphenyl-, phenylsulphinyl- and phenylsulphonyl-pentadienyl metals
  作者：E. Epifani、S. Florio、G. Ingrosso、L. Ronzini、R. Sgarra、L. Troisi

  DOI：10.1016/s0040-4020(01)89751-9

  日期：1991.8

  The coupling reaction of phenylsulphenyl-, phenylsulphinyl- and phenylsulphonyl-pentadienyl metals 3a-g has been studied showing that while 3c-g couple in any case regioselectively and stereoselectively, the coupling of 3a-b is counteraction and electrophile dependent. The alpha-regioisomeric coupling products of phenylsulphenylpentadienyl metals may undergo [1,5] sigmatropic rearrangement, those of phenylsulphinyl- and phenylsulphonyl-pentadienyl metals give fast double [3,2] sigmatropic isomerization.