(Z)-(4-methoxyphenyl)(4-methylstyryl)sulfane | 1449331-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-(4-methoxyphenyl)(4-methylstyryl)sulfane
• 英文别名: (Z)-(4-methylstyryl)(4-methoxyphenyl)sulfane；(Z)-1-methoxy-4-[2-(4-methyl phenyl)ethenyl]sulfanylbenzene；(4-methoxyphenyl)(4-methylstyryl)sulfane；1-methoxy-4-[(Z)-2-(4-methylphenyl)ethenyl]sulfanylbenzene
• CAS: 1449331-04-7
• 化学式: C₁₆H₁₆OS
• 分子量: 256.368
• InChiKey: YIMTUWLNMLRBTF-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 (Z)-1-(2-iodovinyl)-4-methylbenzene 在 K₃PO₄ 、 copper(II) ferrite 、 四丁基溴化铵 作用下， 以 水 为溶剂， 反应 12.0h， 以89%的产率得到(Z)-(4-methoxyphenyl)(4-methylstyryl)sulfane
  参考文献：
  名称：

  磁性可分离的CuFe 2 O 4纳米颗粒在水中催化的无配体CS偶联：进入（E）-和（Z）-苯乙烯基- ，杂芳基和空间受阻的芳基硫醚

  摘要：

  AbstractAn efficient coupling of styrenyl, heteroaryl and sterically hindered aryl halides with aryl‐ and heteroarylthiols catalyzed by the bimetallic Cu and Fe nanomaterial, CuFe2O4, in water in the presence of tetrabutylammonium bromide and potassium phosphate (K3PO4) has been achieved without using any ligand. A series of unsymmetrical functionalized (E)‐ and (Z)‐styrenyl aryl, heteroaryl heteroaryl and sterically hindered aryl aryl sulfides has been obtained by this procedure. The compounds are obtained in high yields and excellent stereoselectivity has been observed for styrenyl sulfides. The catalyst can be easily separated by an external magnet and recycled for ten times without any appreciable loss of activity. This procedure provides an easy access to useful and challenging biologically active organosulfides which are difficult to achieve by other methods.magnified image

  DOI：

  10.1002/adsc.201300261

文献信息

• 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。
• Thiol-Ene “Click” Reaction Triggered by Neutral Ionic Liquid: The “Ambiphilic” Character of [hmim]Br in the Regioselective Nucleophilic Hydrothiolation
  作者：Rajesh Kumar、Saima、Amit Shard、Nitin H. Andhare、Richa、Arun K. Sinha

  DOI：10.1002/anie.201408721

  日期：2015.1.12

  the “ambiphilic” character of the ionic liquid promotes the nucleophilic addition of thiol to styrene through an anti‐Markovnikov pathway. The catalyst recyclability and the extension of the methodology for thiol–yne click chemistry are additional benefits. A competitive study among thiophenol, styrene, and phenyl acetylene revealed that the rate of reaction is in the order of thiol–yne>thiol–ene>dimerization

  硫醇-“咔嗒”化学已成为构建碳-杂原子（CS）键的有力策略，通常会形成两个区域异构体。为此，已经探索了中性离子液体[hmim] Br作为溶剂兼催化剂，用于从活化和失活的苯乙烯衍生物或仲苄醇和硫醇合成线性硫醚，而无需使用金属络合物，碱或自由基引发剂。此外，使用1进行详细的机械研究1 H NMR光谱和四极杆飞行时间电喷雾电离质谱（Q-TOF ESI-MS）表明，离子液体的“两亲”特性通过反马尔可夫尼科夫途径促进了巯基与苯乙烯的亲核加成。催化剂的可回收性和硫醇-炔点击化学方法的扩展是其他好处。硫酚，苯乙烯和苯基乙炔之间的竞争研究表明，反应速率为[hmim] Br中的硫醇-炔>硫醇-烯>硫醇二聚的顺序。
• Synthesis and structural studies of Cu(<scp>i</scp>) methylthiosalicylate complexes and their catalytic application in thiol-yne click reaction
  作者：Krishna Kumar、Priyanka Tiwari、Rajni Kant、Subrato Bhattacharya

  DOI：10.1039/d2nj02722d

  日期：——

  trigonal pyramidal/distorted tetrahedral. The catalytic activities of the complexes towards hydrothiolation of alkynes (via thiol-yne click reaction) have been studied. Out of these three complexes, 2 has been found to be an efficient catalyst for the synthesis of unsymmetrical vinyl sulfide. The desired vinyl sulfides are obtained in good to excellent yields, with up to >99% Z stereoselectivity in

  Cu( I )、[Cu(PPh 3 ) 2 (mts)] ( 1 )、[Cu(dppf)(mts)] ( 2 ) 和 [Cu(dppe)(mts)] 2 ( 3 ) ( mts = 甲基硫代水杨酸盐；dppf = 二苯基膦基二茂铁；dppe = 二苯基膦乙烷），已合成和表征。配合物1和2是单体，而3具有二聚体结构。这些配合物中Cu( I ) 周围的配位几何形状是三角锥体/扭曲的四面体。配合物对炔烃氢硫醇化的催化活性（通过硫醇-炔点击反应）已被研究。在这三种配合物中，2已被发现是合成不对称乙烯基硫化物的有效催化剂。所需的乙烯基硫化物以良好至优异的产率获得，在一种情况下Z立体选择性高达 >99% 。该协议可容忍多种官能团或基材，不含钯，并且不需要使用昂贵或对空气敏感的添加剂。该方法的范围和多功能性已通过几个示例成功地证明。
• 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.