(E)-1-chloro-2-(phenylsulfanyl)hex-1-ene

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-1-chloro-2-(phenylsulfanyl)hex-1-ene
• 英文别名: (E)-1-chloro-2-(phenylthio)hex-1-ene；[(E)-1-chlorohex-1-en-2-yl]sulfanylbenzene
• 化学式: C₁₂H₁₅ClS
• 分子量: 226.77
• InChiKey: PLPFKRBDLYLPDT-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4'-nitrobenzenesulfenanilide 生成 (E)-1-chloro-2-(phenylsulfanyl)hex-1-ene
  参考文献：
  名称：

  Benati Luisa, Capella Laura, Montevecchi Pier Carlo, Spagnolo Piero, Tetrahedron, 50 (1994) N 43, S 12395-12406

  摘要：

  DOI：

文献信息

• Reaction of 4′-nitrobenzenesulfenanilide (NBSA) with Lewis acids. A study of its application in sulfenocyclization of alkenes and alkynes
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1016/s0040-4020(01)89547-8

  日期：1994.1

  from the initial (phenylthiomethyl)- cyclopentyl cation 24. The reaction products are discussed in terms of intermediate thiiranium and thiirenium ions whose decomposition mode is strictly dependent upon their structural features. Novel evidence is also presented that aluminium chloride and bromide can promote reaction of NBSA with alkenes and alkynes to afford chloro- and bromo-sulfenylation adducts

  NBSA已研究了许多具有内部羟基，羧基或乙烯基官能团的烯烃和炔烃的苯磺酰基环化作用。的硫醚4-戊烯-1-醇4以及thiolactonization的4-戊烯-1- OIC酸7，以及在温和的程度，4-戊炔-1- OIC酸8可以与NBSA在存在成功地实现三氟化硼。另一方面，在类似条件下，3-丁烯-1-醇3和3-丁烯-1-油酸6不能进行硫环化，而是生成氧杂和/或氮杂亚磺酰基化的1,2-加合物。用4-pentyn-1-ol 5观察到类似的故障，在这种情况下，二苯二硫和4-硝基苯胺是独家产品。六（1，5-二烯）9在某种程度上提供了环化的芳基氨基硫化物，即23，这归因于亚甲基单元从最初的（苯硫甲基）-环戊基阳离子24形式上的损失。根据中间th离子和th离子讨论了反应产物，它们的分解方式严格取决于它们的结构特征。还提出了新的证据，氯化铝和溴化物可以促进NBSA与烯烃和炔烃的反应，从而以不同的收率提供氯磺酰基和溴磺酰基化加合物。
• Chlorochalcogenation of acetylenes with benzenesulfen-(or selenen)amides and Tin(IV) chloride
  作者：A. V. Martynov、N. A. Makhaeva、S. V. Amosova

  DOI：10.1134/s1070428006070037

  日期：2006.7

  Benzenesulfenainides and benzeneselenenamides reacted with terminal and internal acetylenes (hex-1-yne, phenylacetylene, hex-3-yne, but-2-yne-1,4-diol, and diphenylacetylene) in the presence of SnCl4 to give the corresponding chloroethenyl sulfides and selenides. From symmetric acetylenes, only E isomers (E)-ArXCR=CClR (X = S, Ar = Ph, 4-CIC6H4; R = Et, Ph, HOCH2; X = Se, Ar = Ph, R = Et) were formed. The reactions of benzenesulfenamide with terminal acetylenes, apart from the corresponding Markownikoff and anti-Markownikoff adducts (PhSCH=CCIR and PhSCR=CHCI, R = Bu, Ph) gave ethynyl sulfides PhSC=-CR (R = Ph, Bu) and cis/trans-isomeric 1,2-bis(phenylsulfayl)chloroethenes PhSCR=CClSPh (R = Ph, Bu). The results were interpreted assuming intermediate generation of sulfenyl and selenenyl chlorides via reaction of sulfen- and selenenamides with SnCl4.