(E)-(4-nitrophenyl)(styryl)sulfane | 124447-29-6

• 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: (E)-(4-nitrophenyl)(styryl)sulfane
• 英文别名: 1-nitro-4-[(E)-2-phenylethenyl]sulfanylbenzene
• CAS: 124447-29-6
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: GUSCIMGPTLXFGN-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(4-nitrophenyl)(styryl)sulfane 、 chlorozinc(1+),prop-1-ene 在 正丁基锂 、 三(2-呋喃基)膦 、 nickel dichloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以42%的产率得到(1E)-1,4-pentadienylbenzene
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Coupling Reaction of Allyl- and Benzylzinc with Alkenyl Sulfides

  摘要：

  烯基硫化物可以用于镍催化的交叉偶联反应，与烯丙基和苄基锌试剂反应。

  DOI：

  10.1055/s-2008-1077960
• 作为产物：
  描述：

  2-(4-硝基苯基)硫基-1-苯乙酮 在 sodium tetrahydroborate 、 硫酸 作用下， 生成 (E)-(4-nitrophenyl)(styryl)sulfane
  参考文献：
  名称：

  Ortho effects in organic molecules on electron impact part 22. Competing oxygen transfers from the nitro group to sulphur and the olefinic double bond in 2-nitrophenyl styryl sulphides

  摘要：

  AbstractDouble oxygen migration to sulphur from the ortho‐nitro group leading to eliminations of SO2 and ·SO2H from the molecular ions and single oxygen transfer to the olefinic double bond in the side‐chain giving rise to the most abundant ion at m/z 138 have been observed in 2‐nitrophenyl styryl sulphides on electron impact. The proposed fragmentation mechanisms and the product ion structures were confirmed with the aid of high‐resolution data, B/E linked scan and CID spectra.

  DOI：

  10.1002/oms.1210250308

文献信息

• Copper-mediated stereospecific C–H oxidative sulfenylation of terminal alkenes with disulfides
  作者：Hai-Yong Tu、Bo-Lun Hu、Chen-Liang Deng、Xing-Guo Zhang

  DOI：10.1039/c5cc06250k

  日期：——

  A new copper and iodine-mediated C–H oxidative sulfenylation of olefins with diaryl disulfides for the stereospecific synthesis of vinyl thioether is described.

  描述了一种新的铜和碘介导的C-H氧化磺化方法，使用二芳基二硫化物对烯烃进行立体特异性合成乙烯硫醚。
• Regioselective hydrothiolation of terminal acetylene catalyzed by magnetite (Fe₃O₄) nanoparticles
  作者：Manuela S. T. Rocha、Jamal Rafique、Sumbal Saba、Juliano B. Azeredo、Davi Back、Marcelo Godoi、Antonio L. Braga

  DOI：10.1080/00397911.2016.1262421

  日期：2017.2.16

  ABSTRACT Herein, we report a new and solvent-free methodology for the preparation of vinyl thioethers from terminal alkynes and thiols, using magnetite (Fe3O4) nanoparticles as a recyclable catalyst. With this greener method, the desired vinyl thioethers were achieved in good yields and with good stereoselectivity. In addition, the catalyst was easily recovered using a simple external magnet and reused

  摘要在此，我们报告了一种新的无溶剂方法，用于从末端炔烃和硫醇制备乙烯基硫醚，使用磁铁矿 (Fe3O4) 纳米颗粒作为可回收催化剂。使用这种更环保的方法，以良好的收率和立体选择性获得了所需的乙烯基硫醚。此外，使用简单的外部磁铁很容易回收催化剂，并重新用于进一步的催化反应，直到第五次循环时活性没有显着损失。图形概要
• Stereoselective Formation of<i>Z</i>- or<i>E</i>-Vinyl Thioethers from Arylthiols and Acetylenes under Transition-Metal-Free Conditions
  作者：Yunfeng Liao、Shanping Chen、Pengcheng Jiang、Hongrui Qi、Guo-Jun Deng

  DOI：10.1002/ejoc.201300727

  日期：2013.10

  Vinyl sulfide formation with good yield and high regio- and stereoselectivities from thiols and acetylenes under transition-metal-free conditions is described. Potassium phosphate was used as an effective additive to enhance the reaction yield and selectivity. Z-Vinyl sulfides were predominately formed in the presence of potassium phosphate, whereas E-vinyl sulfides were formed under solvent- and base-free

  描述了在无过渡金属条件下从硫醇和乙炔以高产率和高区域和立体选择性形成乙烯基硫化物。磷酸钾被用作有效的添加剂以提高反应产率和选择性。Z-乙烯基硫化物主要在磷酸钾存在下形成，而 E-乙烯基硫化物在无溶剂和无碱条件下形成。
• Stereoselective Synthesis of Alkenyl Silanes, Sulfones, Phosphine Oxides, and Nitroolefins by Radical C–S Bond Cleavage of Arylalkenyl Sulfides
  作者：Ya-mei Lin、Guo-ping Lu、Rong-kang Wang、Wen-bin Yi

  DOI：10.1021/acs.orglett.7b00126

  日期：2017.3.3

  has been introduced for the C–S bond activation of arylalkenyl sulfides. The protocol provides an efficient approach for the generation of various alkenes including alkenyl silanes, sulfones, phosphine oxides, and nitroolefins. In most cases, these radical substitutions are performed under metal-free conditions with stereospecificity.

  引入了自由基介导的方法来活化芳基烯基硫醚的C–S键。该协议为生成各种烯烃（包括烯基硅烷，砜，氧化膦和硝基烯烃）提供了一种有效的方法。在大多数情况下，这些自由基取代是在无金属的立体定向条件下进行的。
• Decarbonylation of Salicylaldehyde Activated by<i>p</i>-Cymene Ruthenium(II) Dimer: Implication for Catalytic Alkyne Hydrothiolation
  作者：Sarangapani Modem、Shravankumar Kankala、Ramesh Balaboina、Narasimha Swamy Thirukovela、Sreekantha B. Jonnalagadda、Ravinder Vadde、Chandra Sekhar Vasam

  DOI：10.1002/ejoc.201600809

  日期：2016.9

  A stoichiometric C–H activation/decarbonylation of salicylaldehyde by [(η6-p-cymene)RuCl2]2 gave a carbonyl derivative [(η6-p-cymene)RuCl(CO)(Ph-O)] (1) without the use of CO gas. A variety of polar phosphines were then incorporated into compound 1 to give new RuII cationic catalysts, [(η6-p-cymene)Ru(CO)(Ph-O)L]BF4 (2–8). These were used to catalyse the hydrothiolation of alkynes with a range of thiols

  [(η6-p-cymene)RuCl2]2 化学计量的 C-H 活化/脱羰水杨醛得到羰基衍生物 [(η6-p-cymene)RuCl(CO)(Ph-O)] (1)，但不使用一氧化碳气体。然后将各种极性膦掺入化合物 1 中以得到新的 RuII 阳离子催化剂，[(η6-p-伞花烃)Ru(CO)(Ph-O)L]BF4 (2-8)。它们用于在四氢呋喃水溶液中催化炔烃与一系列硫醇的氢硫醇化反应，以高产率得到抗马尔科夫尼科夫 E-线性乙烯基硫化物。