(Z)-(4-nitrophenyl)(styryl)sulfane | 1372796-36-5

• 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-nitrophenyl)(styryl)sulfane
• 英文别名: 1-nitro-4-[(Z)-2-phenylethenyl]sulfanylbenzene
• CAS: 1372796-36-5
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: GUSCIMGPTLXFGN-KHPPLWFESA-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

• 作为产物：
  描述：

  苯乙炔 、 4-硝基苯硫醇 在 indium(III) triflate 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以75%的产率得到(Z)-(4-nitrophenyl)(styryl)sulfane
  参考文献：
  名称：

  Indium(iii) catalysed substrate selective hydrothiolation of terminal alkynes

  摘要：

  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。

  DOI：

  10.1039/c2cc30350g

文献信息

• 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。
• 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。
• Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide
  作者：Cheng-Ming Chu、Zhijay Tu、Pohsi Wu、Chieh-Chieh Wang、Ju-Tsung Liu、Chun-Wei Kuo、Yu-Hsuan Shin、Ching-Fa Yao

  DOI：10.1016/j.tet.2009.02.074

  日期：2009.5

  Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.

  在无催化剂的反应条件下，溶剂介导的硫醇2加到β-硝基苯乙烯1中进行区域选择性控制，以良好或极好的收率得到加合物3或乙烯基硫化物4。为了使形成的产物合理化，提出了热力学和自催化反应机理。
• Regioselective Hydrothiolation of Alkynes by Sulfonyl Hydrazides Using Organic Ionic Base–Brønsted Acid
  作者：Rahul Singh、Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.1021/ol401925u

  日期：2013.8.16

  A practical and novel approach has been developed for the synthesis of vinyl sulfides by the reaction of sulfonyl hydrazides with aryl/heteroarylacetylenes using a DBU-based ionic liquid. The system offers a new sulfur source for hydrothiolation and is endowed with green credentials.