(E)-4-(styrylthio)aniline | 1189143-61-0

• 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: (E)-4-(styrylthio)aniline
• 英文别名: 4-[(E)-2-phenylethenyl]sulfanylaniline
• CAS: 1189143-61-0
• 化学式: C₁₄H₁₃NS
• 分子量: 227.33
• InChiKey: IYPINGCZUGEJLW-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-dibromostyrene 在 Ni(xantphos)(o-tolyl)Cl 、 potassium acetate 、 三乙胺 、 亚磷酸二甲酯 、 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 13.5h， 生成 (E)-4-(styrylthio)aniline
  参考文献：
  名称：

  镍催化实现的烯基硫醚化

  摘要：

  本文描述了一种有效的策略，通过镍催化的失活或 β-芳基取代的 ( E )-烯基卤化物与硫醇/酚的交叉偶联来促进烯基硫醚化。本策略具有易于操作的反应条件，代表了通过易于获得的镍催化形成最有效的烯基 C(sp 2 )–S 键的方法之一。值得注意的是，所采用的温和碱性条件有助于获得广泛的范围，包括受保护的氨基酸、糖类和杂环化合物。此外，这项工作通过在几种结构复杂的天然产物和药物的后期修饰中的应用展现了其极具吸引力的实用性。

  DOI：

  10.1021/acs.joc.3c00049

文献信息

• 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。
• Anti-Markovnikov stereoselective hydroamination and hydrothiolation of (hetero)aromatic alkynes using a metal-free cyclic trimeric phosphazene base
  作者：Na Zhao、Chengdong Lin、Lirong Wen、Zhibo Li

  DOI：10.1016/j.tet.2019.04.075

  日期：2019.6

  Hydroamination and hydrothiolation are the most efficient and completely atom-economical process to construct important enamine and vinyl sulfide intermediates in pharmaceutical and organic chemistry. The cyclic trimeric phosphazene base (CTPB) showed great catalytic activity for the anti-Markovnikov stereoselective hydroamination and hydrothiolation of alkynes in good to excellent yields. A broad

  加氢胺化和加氢硫醇化是在药物和有机化学中构建重要的烯胺和乙烯基硫化物中间体的最有效且完全原子经济的过程。环状三聚磷腈碱（CTPB）对炔烃的抗马尔可夫尼科夫立体选择性加氢胺化和加氢硫醇化反应显示出很高的催化活性，收率良好。炔烃和亲核试剂的广泛底物范围得到证实，包括芳基和杂芳基炔烃，末端和内部炔烃，不同的N-杂环，硫醇和苯硫酚。这种通用且具有成本效益的方法，具有良好的立体选择性和出色的官能团耐受性，为炔烃的有机催化加氢官能化提供了新机会。
• 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.
• Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides
  作者：Pablo R. Sacasa、Jessica Zayas、Stanislaw F. Wnuk

  DOI：10.1016/j.tetlet.2009.07.063

  日期：2009.9

  Radical-mediated thiodesulfonylation of the vinyl and (alpha-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (a-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones. (C) 2009 Elsevier Ltd. All rights reserved.