1-methoxy-4-(2-phenylvinylsulfanyl)benzene | 193883-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methoxy-4-(2-phenylvinylsulfanyl)benzene
• 英文别名: (4-methoxyphenyl)(styryl)sulfane；1-methoxy-4-(2-phenylethenylsulfanyl)benzene
• CAS: 193883-11-3
• 化学式: C₁₅H₁₄OS
• 分子量: 242.342
• InChiKey: LLLCPSOBXBVEEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  385.9±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-methoxy-4-(2-phenylvinylsulfanyl)benzene 在 高氯酸 、 ammonium vanadate 、 溶剂黄146 作用下， 反应 36.0h， 生成 4,4'-二甲氧基二苯二硫 、 苯乙醛
  参考文献：
  名称：

  Karunakaran, Kolandaivelu; Elango, Kuppanagounder Pitchaimuthu, Journal of the Indian Chemical Society, 1997, vol. 74, # 4, p. 299 - 301

  摘要：

  DOI：
• 作为产物：
  描述：

  氧化苯乙烯 、 4-甲氧基苯硫酚 在 Amberlyst-15 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以85%的产率得到1-methoxy-4-(2-phenylvinylsulfanyl)benzene
  参考文献：
  名称：

  Amberlyst-15©: An efficient heterogeneous reusable catalyst for selective anti-Markovnikov addition of thiols to alkenes/alkynes and for thiolysis of epoxides

  摘要：

  The anti-Markovnikov addition of thiols to alkenes/alkynes and thiolysis of epoxides is described using Amberlyst-15(C) as a selective, commercially available, inexpensive and reusable catalyst. The products like diorganyl sulphides, beta-hydroxy sulphides and phenyl(styryl)sulfanes were obtained in good to excellent yields in short reaction time and with high regio-selectivity. The catalyst was reused up to five consecutive recycles without any loss in its catalytic activity. The developed methodology is a metal free protocol for C-S bond formation reaction with high atom economy. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2013.06.032

文献信息

• Potassium tert-Butoxide Mediated Reductive C–P Cross-Coupling of Arylvinyl Sulfides through C–S Bond Cleavage
  作者：Qingle Zeng、Jie Feng、Qiaoling Zhang、Fuhai Li、Lu Yang、Ratnakar Reddy Kuchukulla

  DOI：10.1055/s-0040-1707319

  日期：2021.1

  transition-metal-free t-BuOK-mediated reductive C–P cross-coupling reaction of arylvinyl sulfides with diarylphosphine oxides through C–S bond cleavage has been developed. This protocol not only permits the synthesis of diaryl(2-arylethyl)phosphine oxides, but also achieves an unprecedented construction of a C–P bond through C–S bond cleavage and reduction of a C–C double bond in one pot.

  已经开发出一种无过渡金属的 t-BuOK 介导的芳基乙烯基硫化物与二芳基氧化膦通过 C-S 键断裂的还原 C-P 交叉偶联反应。该协议不仅允许合成二芳基（2-芳基乙基）氧化膦，而且还通过 C-S 键断裂和一锅 C-C 双键的还原实现了前所未有的 C-P 键构建。
• 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。
• 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。
• Regio- and stereoselective synthesis of vinyl sulfides via PhSeBr-catalyzed hydrothiolation of alkynes
  作者：Flávia Manarin、Juliano A. Roehrs、Marina Prigol、Diego Alves、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1016/j.tetlet.2007.05.076

  日期：2007.7

  We present here a simple and mild method of hydrothiolation of internal and terminal alkynes under PhSeBr-catalyzed reaction in the absence of solvent at room temperature. The reaction tolerates a wide variety of substituents on thiol, and provides the corresponding product in good yield and selectivity. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.