(E)-[2-(phenylsulfanyl)vinyl]benzene | 7214-53-1

• 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: (E)-[2-(phenylsulfanyl)vinyl]benzene
• 英文别名: (E)-phenyl(styryl)sulfane；phenyl(styryl)sulfane；(E)-styryl phenyl sulfide；(E)-β-(phenylthio)styrene；phenyl styryl sulfide；[(E)-2-(Phenylsulfanyl)ethenyl]benzene；[(E)-2-phenylethenyl]sulfanylbenzene
• CAS: 7214-53-1
• 化学式: C₁₄H₁₂S
• 分子量: 212.315
• InChiKey: NCSYOCXYJXZCGQ-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 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：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-[2-(phenylsulfanyl)vinyl]benzene 在 manganese(IV) oxide 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89.3%的产率得到(1,2-Dichloro-2-phenylethyl)sulfanylbenzene
  参考文献：
  名称：

  Bellesia, Franco; Ghelfi, Franco; Pagnoni, Ugo Maria, Gazzetta Chimica Italiana, 1993, vol. 123, # 5, p. 289 - 291

  摘要：

  DOI：
• 作为产物：
  描述：

  氯甲基苯硫醚 在 正丁基锂 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 (E)-[2-(phenylsulfanyl)vinyl]benzene
  参考文献：
  名称：

  Homologation of aldehydes using (phenylthiomethylene) triphenylarsorane: selective preparation of α-thiophenoxyepoxides and phenylthioenol ethers

  摘要：

  DOI：

  10.1016/s0040-4039(01)93844-4

文献信息

• Highly regio- and stereoselective hydrothiolation of acetylenes with thiols catalyzed by a well-defined supported Rh complex
  作者：Yong Yang、Robert M. Rioux

  DOI：10.1039/c1cc11605c

  日期：——

  Highly regio- and stereoselective hydrothiolation of a wide range of alkynes with various thiols was demonstrated in the presence of a well-defined Rh complex supported on mesoporous SBA-15 silica. The catalyst was easily recovered and reused several times without significant loss of activity or selectivity.

  在存在于介孔SBA-15二氧化硅上的明确定义的Rh配合物的存在下，证明了各种炔与各种硫醇的高度区域选择性和立体选择性氢硫醇化作用。催化剂容易回收并重复使用几次，而活性或选择性没有明显损失。
• Lanthanum-catalyzed stereoselective synthesis of vinyl sulfides and selenides
  作者：V. Prakash Reddy、K. Swapna、A. Vijay Kumar、K. Rama Rao

  DOI：10.1016/j.tetlet.2009.11.004

  日期：2010.1

  oxide/TMEDA-catalyzed cross-coupling of vinyl halides with thiols/diphenyl diselenide in anhydrous DMSO and KOH is reported. Utilizing this protocol various vinyl sulfides and selenides were synthesized in excellent yields with retention of the stereochemistry. The catalyst was recyclable.

  据报道，在无水DMSO和KOH中，氧化镧/ TMEDA催化卤代乙烯与硫醇/二苯基二硒化物的交叉偶联。利用该方案，以优异的产率合成了各种乙烯基硫化物和硒化物，并保留了立体化学。该催化剂是可回收的。
• A Simplified Protocol for the Stereospecific Nickel-Catalyzed C–S Vinylation Using NiX2 Salts and Alkyl Phosphites
  作者：Austin D. Marchese、Bijan Mirabi、Egor M. Larin、Mark Lautens

  DOI：10.1055/s-0039-1690717

  日期：2020.1

  A Ni-catalyzed C–S cross-coupling using only NiI2 (0.5–2.5 mol%) and P(OiPr)3 (2.0–10.0 mol%) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.

  据报道，仅使用NiI 2（0.5–2.5 mol％）和P（O i Pr）3（2.0–10.0 mol％）的Ni催化的C–S交叉偶联。使用空气稳定的Ni（II）预催化剂和便宜的市售配体，开发了一种可扩展且稳健的方法来交叉偶联各种硫酚和苯乙烯基溴化物，包括一些空间受限的硫醇，α-溴肉桂醛和硫醇化环化。
• Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water
  作者：Ya-mei Lin、Guo-ping Lu、Gui-xiang Wang、Wen-bin Yi

  DOI：10.1021/acs.joc.6b02459

  日期：2017.1.6

  can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents

  引入了一种新开发的含有酸和磷的水性体系，在该体系中，无味且稳定的芳基亚磺酸钠可以原位生成芳基亚硫基。这些自由基具有与炔烃，烯烃和H-膦氧化物反应的高反应性，以合成烷基硫化物和烯基硫化物以及硫代磷酸硫代酸酯。还进行了控制实验和量子计算，以深入了解芳基亚硫基自由基的生成机理。值得注意的是，该化学物质不含硫醇气味，有机溶剂和金属。
• Amino acid and water-driven tunable green protocol to access S–S/C–S bonds via aerobic oxidative coupling and hydrothiolation
  作者：Amit Shard、Rajesh Kumar、Saima Saima、Nidhi Sharma、Arun K. Sinha

  DOI：10.1039/c4ra02909g

  日期：——

  Arginine in conjunction with water has been employed as an effective and recyclable organocatalyst for oxidative coupling of thiophenols and hydrothiolation of alkynes.

  精氨酸与水结合被用作噻吩酚的氧化偶联和炔烃的氢硫化反应的有效可循环有机催化剂。