Hex-1-en-1-yl phenyl sulfide | 86887-87-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Hex-1-en-1-yl phenyl sulfide
• 英文别名: 1-hexenyl phenyl sulfide；1-(Phenylthio)hex-1-ene；1-phenylthiohex-1-ene；Hex-1-enylsulfanylbenzene
• CAS: 86887-87-8
• 化学式: C₁₂H₁₆S
• 分子量: 192.325
• InChiKey: GZKFXALNMQIPEX-UHFFFAOYSA-N

物化性质

• 沸点：
  277.5±13.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 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

• 作为反应物：
  描述：

  Hex-1-en-1-yl phenyl sulfide 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 (hex-1Z-ene-1-sulfonyl)benzene 、 [(trans-hex-1-ene)-1-sulfonyl]benzene
  参考文献：
  名称：

  Benati, Luisa; Capella, Laura; Montevecchi, Pier Carlo, Journal of the Chemical Society. Perkin transactions I, 1995, # 8, p. 1035 - 1038

  摘要：

  DOI：
• 作为产物：
  描述：

  正戊醛 、 三甲基(苯硫甲基)硅烷 在 正丁基锂 作用下， 生成 Hex-1-en-1-yl phenyl sulfide
  参考文献：
  名称：

  Ager, David J., Journal of the Chemical Society. Perkin transactions I, 1986, p. 183 - 194

  摘要：

  DOI：

文献信息

• One-pot dialkylation of allylphenylsulfide induced by aminoalkoxides-activated NaNH2. Application to the synthesis of unsymmetrical ketones
  作者：Sabine Choppin、Philippe Gros、Yves Fort

  DOI：10.1016/s0040-4020(99)00481-0

  日期：1999.7

  aminoalkoxides, leading to new superbases, induced an efficient one-pot dialkylation of allylphenylsulfide. The regioselectivity of the reaction (α,α′ vs α,γ) was found as strongly dependent on the nature of the alkyl halide. As an application, α,γ dialkylated products were efficiently converted into the corresponding unsymmetrical ketones.

  结果表明，氨基醇钠对NaNH 2的活化导致了新的超碱，从而诱导了烯丙基苯硫醚的有效一锅二烷基化。发现反应的区域选择性（α，α'对α，γ）强烈依赖于卤代烷的性质。作为应用，α，γ二烷基化产物被有效地转化为相应的不对称酮。
• THIOL MEDIATED 5-(π-<i>ENDO)ORTHO</i> VINYL RADICAL CYCLIZATIONS
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1080/10426500008076542

  日期：2000.1.1

  Abstract The radical reaction of benzenethiol with alkynes 1a-o carried out at 154 °C affords a mixture of thiol/alkyne adduct 3 and benzothiophene 5, deriving from vinyl radical intermediates 2 through hydrogen abstraction and 5-(π-endo)orthocyclization onto the adjacent thiophenyl ring, respectively. This latter reaction occurs through the reversible formation of cyclohexadienyl radical intermediates

  摘要 苯硫醇与炔烃 1a-o 的自由基反应在 154 °C 下进行，得到硫醇/炔烃加合物 3 和苯并噻吩 5 的混合物，通过夺氢和 5-（π-内）正环化衍生自乙烯基自由基中间体 2。相邻的苯硫环，分别。后一反应通过环己二烯基自由基中间体 4 的可逆形成而发生，其可以在很大程度上取决于所采用的反应条件而演变为 5。5-邻位环化受立体电子因素的控制，有利于 p 中心的线性 α-芳基乙烯基自由基 2a-f 的环化，以及极性因素，有利于 α-EWG 取代的乙烯基自由基 2c,n,o 的环化.
• One electron transfer reaction of phenyl vinyl sulfides with dioxygen. The fate of the intermediate vinyl sulfide radical cations.
  作者：Luisa Benati、Pier Carlo Montevecchi、Daniele Nanni、Piero Spagnolo

  DOI：10.1016/s0040-4039(00)73645-8

  日期：1993.5

  Mild reaction of pheyl vinyl sulfides with dioxygen can lead to the eventual formation of rearranged vinyl sulfides and/or carbonyl-containing sulfide products, which are believed to result from decomposition of initially-formed vinyl sulfide radical cations. Supporting evidence is provided by the comparable findings obtained from the one electron oxidation of one vinyl sulfide by cerium (IV) ammonium

  苯基乙烯基硫化物与双氧的温和反应可导致最终形成重排的乙烯基硫化物和/或含羰基的硫化物产物，据信这是由于最初形成的乙烯基硫化物自由基阳离子的分解所致。硝酸铈（IV）对一种乙烯基硫化物的一次电子氧化获得的可比发现提供了支持性证据。
• CAN- and DDQ-Promoted Oxidation of Alkenyl Sulfides
  作者：Laura Capella、Pier Carlo Montevecchi、Daniele Nanni

  DOI：10.1021/jo00103a033

  日期：1994.12

  Vinyl sulfides 1 react with CAN in acetonitrile at room temperature to give radical cations 2A in equilibrium with the thiiranyl radical cations 2B. The reaction products arise from nucleophilic attack of the nitrate counterion at either the sulfur atom of 2A or the trivalent carbon of 2B. The last reaction can proceed through 1,2-shift or displacement of the sulfide moiety. When alpha-methylenic protons are present in 2B, deprotonation occurs, leading to allyl radicals and, ultimately, to isomeric allyl alcohols. Reactions of 1 with DDQ in acetonitrile afford charge-transfer complexes and then zwitterionic electron-transfer (ET) complexes which can evolve rapidly through intramolecular proton transfer when trans methylenic protons are present. The resulting sulfur-oxygen sigma-complexes are responsible for the reaction products mainly through either gamma-elimination of DDQH(2) or nucleophilic attack at the delta-vinylic carbon followed by displacement of DDQH(-).