(Z)-1-(Allylthio)-2-phenylethylene | 42442-59-1

• 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: (Z)-1-(Allylthio)-2-phenylethylene
• 英文别名: (Z)-1-Allylsulfanyl-2-phenylethene；cis-β-Phenylvinylallylsulfid；cis-Allyl-2-phenylvinylsulfid；[(Z)-2-prop-2-enylsulfanylethenyl]benzene
• CAS: 42442-59-1
• 化学式: C₁₁H₁₂S
• 分子量: 176.282
• InChiKey: FMKRJXZBZDZTRO-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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

• 作为产物：
  描述：

  (phenylacetyl)trimethylsilane 在 盐酸 、 硫化氢 、 potassium carbonate 、 cesium fluoride 作用下， 以 乙醚 、 二甲基亚砜 、 丙酮 为溶剂， 生成 (Z)-1-(Allylthio)-2-phenylethylene
  参考文献：
  名称：

  Chemistry of silyl thioketones. Part 10. Synthesis and reactivity of α-silyl vinyl sulfides

  摘要：

  Aliphatic silyl thioketones containing an alpha-hydrogen atom undergo enethiolization to Z-alpha-silyl enethiols 2. Compounds 2 react with a variety of halides R(3)X to give open-chain alpha-silyl vinyl sulfides 3. Protiodesilylation of 3 was achieved upon treatment with fluoride ion to give vinyl sulfides 4. Reaction of 3 with Grignard reagents, in the presence of an appropriate nickel catalyst, results in a series of vinylsilanes 5 with a specific geometry.

  DOI：

  10.1039/p19960002803

文献信息

• CuI-catalyzed regioselective hydrothiolation of alkynes: a thiol-free route to (<i>Z</i>)-β-alkenyl sulfides
  作者：Najmeh Nowrouzi、Mohammad Abbasi、Ensieh Safari、Amin Arman

  DOI：10.1039/d3ob01230a

  日期：——

  A thiol-free procedure for regioselective preparation of (Z)-β-alkenyl sulfides via a three-component reaction of aryl/alkyl halides, phenylacetylene, and potassium isopropylxanthate in the presence of copper iodide as a catalyst in polyethylene glycol is reported. In this study, a xanthate salt is used as an odorless source of sulfur. The reactions proceed in a one-pot and single-step pathway with

  报道了在碘化铜作为催化剂的聚乙二醇存在下，通过芳基/烷基卤化物、苯乙炔和异丙基黄原酸钾的三组分反应，无硫醇区域选择性制备( Z )-β-烯基硫醚的方法。在这项研究中，黄原酸盐被用作无味的硫源。该反应以一锅单步途径进行，形成使用 NMR 数据鉴定的碳酸氢盐中间体，并专门形成Z异构体。
• Free-Radical Addition of Alkanethiols to Alkynes. Rearrangements of the Intermediate .beta.-(Vinylthio) Radicals
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1021/jo00089a030

  日期：1994.5

  A variety of 2-mercapto-substituted vinyl radicals have been produced through the free-radical reaction of alkanethiols (including phenethyl, allyl, and benzyl mercaptans) with monosubstituted acetylenes in benzene at 90 degrees C. The 8-(benzylthio)vinyl radicals 6 readily rearranged to (vinylthio)methyl radicals 7 via a novel 1,4-migration of the phenyl group from thiomethyl to vinyl carbon; 2- (phenethylthio)vinyl radicals 12 underwent internal 1,5-hydrogen transfer to form beta-thio-substituted benzyl radicals 13 which in turn suffered fast beta-elimination of vinylthio radicals 18; and 2-(allylthio)vinyl radical 20 underwent kinetically preferred 5-exo cyclization to give the primary radical 26 which could easily rearrange to the more stable ring-expanded radical 25.