(Z)-β-(β'-naphthylthio)styrene | 929544-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-β-(β'-naphthylthio)styrene
• 英文别名: (Z)-naphthalen-2-yl(styryl)sulfane；naphthalen-2-yl(styryl)sulfane；2-[(Z)-2-phenylethenyl]sulfanylnaphthalene
• CAS: 929544-33-2
• 化学式: C₁₈H₁₄S
• 分子量: 262.375
• InChiKey: ZMFQALZJUYCFLW-SEYXRHQNSA-N

物化性质

• 沸点：
  437.9±28.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  (Z)-β-(β'-naphthylthio)styrene 在 aluminum oxide 、 Oxone 作用下， 以75%的产率得到(Z)-2-naphthyl styryl sulfoxide
  参考文献：
  名称：

  Diederichs, Sophie; Simonet, Jacques, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 6, p. 561 - 570

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙炔 、 2-萘硫醇 在 potassium phosphate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以73%的产率得到(Z)-β-(β'-naphthylthio)styrene
  参考文献：
  名称：

  在无过渡金属条件下由芳硫醇和乙炔立体选择性地形成Z-或E-乙烯基硫醚

  摘要：

  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。

  DOI：

  10.1002/ejoc.201300727

文献信息

• l-Proline promoted cross-coupling of vinyl bromide with thiols catalyzed by CuBr in ionic liquid
  作者：Yunfa Zheng、Xingfen Du、Weiliang Bao

  DOI：10.1016/j.tetlet.2005.11.164

  日期：2006.2

  the coupling of vinyl bromides with thiols using the copper(I) bromide as catalyst and l-proline as ligand was reported. The best yields were obtained in the ionic liquid [Bmim]BF4 with the retention of stereochemistry. This protocol is palladium-free, tolerates both aromatic and aliphatic thiols, possesses good selectivity between alcohol and thiol, and does not require the use of expensive or air-sensitive

  报道了一种以溴化铜（I）为催化剂，以l-脯氨酸为配体，通过使溴化乙烯与硫醇偶合来合成硫化乙烯的方法。在离子液体[Bmim] BF 4中获得了最佳收率，并且保留了立体化学。该方案不含钯，可耐受芳族和脂族硫醇，在醇和硫醇之间具有良好的选择性，并且不需要使用昂贵或对空气敏感的添加剂。
• Carbon Dioxide Mediated Stereoselective Copper-Catalyzed Reductive Coupling of Alkynes and Thiols
  作者：Siti Nurhanna Riduan、Jackie Y. Ying、Yugen Zhang

  DOI：10.1021/ol3003699

  日期：2012.4.6

  A simple protocol for the stereoselective copper-catalyzed hydrothiolation of alkynes under a CO2 atmosphere has been developed. The stereoselectivity is determined by the presence/absence of a CO2 atmosphere. The reaction system is robust and utilizes inexpensive, readily available substrates. A cyclic alkene/carboxylate copper complex intermediate is proposed as the key step in determining the stereoselectivity

  已经开发了在CO 2气氛下立体选择性铜催化炔烃的氢硫醇化的简单方案。立体选择性取决于是否存在CO 2气氛。该反应系统坚固耐用，并利用廉价，易于获得的底物。提议将环状烯烃/羧酸铜络合物中间体作为确定立体选择性的关键步骤，并且发现当量的水起质子供体的作用。
• Mild, Efficient and Highly Stereoselective Synthesis of (<i>Z</i>)-Vinyl Chalcogenides from Vinyl Bromides Catalyzed by Copper(I) in Ionic Liquids Based on Amino Acids
  作者：Weiliang Bao、Zhiming Wang、Hanjie Mo

  DOI：10.1055/s-2006-958413

  日期：2007.1

  A method for the synthesis of(Z)-vinyl chalcogenides by the coupling of vinyl bromides with thiols or diphenyl diselenide using copper(I) salts as catalysts in ionic liquids based on amino acids is reported. The desired vinyl chalcogenides were obtained in good to excellent yields with retention of stereochemistry. The ionic liquids play multiple roles in the reaction: they act as solvent, base, and

  报道了一种在基于氨基酸的离子液体中使用铜 (I) 盐作为催化剂，通过乙烯基溴化物与硫醇或二苯基二硒化物偶联合成 (Z)-乙烯基硫属元素化物的方法。以良好至极好的收率获得了所需的乙烯基硫属化物，同时保留了立体化学。离子液体在反应中起着多种作用：它们作为溶剂、碱和铜催化偶联反应的优良促进剂。
• Photochemical halogen-bonding assisted generation of vinyl and sulfur-centered radicals: stereoselective catalyst-free C(sp²)–S bond forming reactions
  作者：Helena F. Piedra、Manuel Plaza

  DOI：10.1039/d2sc05556b

  日期：——

  formation of highly reactive vinyl radicals would be a feasible process for the photochemical cross-coupling between thiols and alkenyl halides under basic conditions. The reaction shows indeed a very broad functional group tolerance, is stereoselective, simple and scalable. In-depth mechanistic studies point at the formation of vinyl and sulfur-centered radicals as the intermediates of the reaction and

  光化学和卤键相互作用的结合在过去几年中兴起，成为在温和条件下产生自由基中间体的强大合成工具。在以碳为中心的自由基的形成中，这种反应性迄今为止仅限于使用芳基和烷基卤化物作为前体。我们现在设想，卤素键合引发的高反应性乙烯基自由基的形成将是硫醇和烯基卤化物在碱性条件下进行光化学交叉偶联的可行过程。该反应确实显示出非常广泛的官能团耐受性、立体选择性、简单且可扩展。深入的机理研究指向乙烯基和以硫为中心的自由基的形成作为反应的中间体，DFT 计算支持卤键复合物的预形成作为光化学转化的引发剂。开发了综合应用程序以扩展该方法的实用性。
• Synthesis of Vinyl Sulfides by Copper-Catalyzed Decarboxylative C−S Cross-Coupling
  作者：Sadananda Ranjit、Zhongyu Duan、Pengfei Zhang、Xiaogang Liu

  DOI：10.1021/ol101729k

  日期：2010.9.17

  A novel method for the synthesis of vinyl sulfides by the decarboxylative cross-coupling of arylpropiolic acids with thiols using copper(I) salts as catalysts has been developed. In the presence of Cul and Cs2CO3, a variety of thiols reacted with arylpropiolic acids to afford the corresponding vinyl sulfides in good to excellent yields with high stereoselectivity for Z-isomers.