(Z)-(4-bromophenyl)(styryl)sulfane | 27691-21-0

• 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: (Z)-(4-bromophenyl)(styryl)sulfane
• 英文别名: cis-2-(4-Brom-phenylmercapto)-1-phenyl-ethylen；p-Bromphenyl-cis-styrylsulfid；1-bromo-4-[(Z)-2-phenylethenyl]sulfanylbenzene
• CAS: 27691-21-0；32228-17-4；32228-22-1
• 化学式: C₁₄H₁₁BrS
• 分子量: 291.211
• InChiKey: FKKUQAZEUNGNJC-KHPPLWFESA-N

物化性质

• 熔点：
  75 °C
• 沸点：
  390.3±42.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 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：

  (Z)-(4-bromophenyl)(styryl)sulfane 在 双氧水 、 溶剂黄146 作用下， 生成 p-Bromphenyl-cis-styrylsulfon
  参考文献：
  名称：

  Baliah,V.; Rathinasamy,T.K., Indian Journal of Chemistry, 1971, vol. 9, p. 220 - 225

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯硫酚 、 苯丙炔酸 在 copper(l) iodide 、 caesium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以88%的产率得到(Z)-(4-bromophenyl)(styryl)sulfane
  参考文献：
  名称：

  Synthesis of Vinyl Sulfides by Copper-Catalyzed Decarboxylative C−S Cross-Coupling

  摘要：

  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.

  DOI：

  10.1021/ol101729k

文献信息

• Zinc-Catalyzed Synthesis of Dithioacetals through Double Hydrosulfenylation of Alkynes by Thiols
  作者：Nobukazu Taniguchi、Kenji Kitayama

  DOI：10.1055/s-0037-1610302

  日期：2018.12

  various solvents, and the corresponding products are obtained regioselectively. Dihydrosulfenylation of alkynes with thiols can also be achieved by using a zinc catalyst, and the reaction is preferentially promoted over monohydrosulfenylation. The reaction can also give dithioacetals regioselectively in excellent yields.

  锌催化烯烃氢磺基化反应可以在多种溶剂中进行，并通过区域选择性得到相应的产物。炔烃与硫醇的二氢硫基化也可以通过使用锌催化剂来实现，并且该反应优先于单氢硫基化。该反应还可以区域选择性地以优异的产率得到二硫代缩醛。
• Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex
  作者：Yong Yang、Robert M. Rioux

  DOI：10.1039/c4gc00642a

  日期：——

  A robust silica-supported Cu-NHC complex catalyzed highly stereoselective anti-Markovnikov hydrothiolation of alkynes or electron-deficient alkenes to construct C–S bonds.

  一种强大的硅支撑的Cu-NHC复合物催化高立体选择性的炔烃或电子亏缺烯烃的反Markovnikov加硫反应，以构建C-S键。
• Indium(iii) catalysed substrate selective hydrothiolation of terminal alkynes
  作者：Rupam Sarma、Nimmakuri Rajesh、Dipak Prajapati

  DOI：10.1039/c2cc30350g

  日期：——

  In(OTf)3 is reported as the first catalyst having the ability to selectively catalyse both Markovnikov and anti-Markovnikov hydrothiolation of terminal alkynes under identical reaction conditions depending upon the nature of the thiol employed.

  据报道，In(OTf)3是首个催化剂，能够在相同的反应条件下，根据所用硫醇的性质，选择性地催化端炔的 Markovnikov 和 anti-Markovnikov 氢硫化反应。
• Hydrothiolation of Alkenes and Alkynes Catalyzed by 3,4-Dimethyl-5-vinylthiazolium iodide and Poly(3,4-dimethyl-5-vinylthiazolium) iodide
  作者：Supill Chun、Junyong Chung、Ji Eun Park、Young Keun Chung

  DOI：10.1002/cctc.201600363

  日期：2016.8.8

  The highly selective anti‐Markovnikov addition of thiols to unactivated alkenes and alkynes was demonstrated by using 3,4‐dimethyl‐5‐vinylthiazolium iodide or its polymer, poly(3,4‐dimethyl‐5‐vinylthiazolium) iodide, as a complementary catalyst. The reaction proceeded cleanly under base‐free conditions in air with both aromatic and aliphatic thiols. The polymer catalyst showed a high turnover number

  通过使用3,4-二甲基-5-乙烯基噻唑鎓碘化物或其聚合物碘化聚（3,4-二甲基-5-乙烯基噻唑鎓）碘作为辅助催化剂，证明了硫醇在未活化的烯烃和炔烃中的高选择性抗Markovnikov加成反应。 。该反应在无碱条件下于空气中与芳香族和脂肪族硫醇一起干净地进行。该聚合物催化剂显示出高周转率（≈5800），可以重复使用多达四次而不会损失任何催化活性。DFT计算支持噻唑鎓阳离子稳定噻吩基中间体，这导致自由基与不饱和C-C键反应。
• 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。