(Z)-ethyl 3-(4-chlorophenylthio)acrylate | 1202656-13-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-ethyl 3-(4-chlorophenylthio)acrylate
• 英文别名: ethyl (Z)-3-(4-chlorophenylthio)acrylate；ethyl (Z)-3-(4-chlorophenyl)sulfanylprop-2-enoate
• CAS: 1202656-13-0
• 化学式: C₁₁H₁₁ClO₂S
• 分子量: 242.726
• InChiKey: OKGIQUZJMLBMIU-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  顺式-3-碘丙烯酸乙酯 、 4-氯苯硫酚 在 copper(II) oxide 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以92%的产率得到(Z)-ethyl 3-(4-chlorophenylthio)acrylate
  参考文献：
  名称：

  无配体条件下可回收纳米氧化铜催化立体选择性合成乙烯基硫化物

  摘要：

  报道了在无配体条件下由可回收的 CuU 纳米粒子催化的乙烯基卤化物与硫醇的交叉偶联的简单有效的协议。这种方法可以以极好的收率合成各种乙烯基硫化物，同时保留立体化学。

  DOI：

  10.1055/s-0029-1217990

文献信息

• Lanthanum-catalyzed stereoselective synthesis of vinyl sulfides and selenides
  作者：V. Prakash Reddy、K. Swapna、A. Vijay Kumar、K. Rama Rao

  DOI：10.1016/j.tetlet.2009.11.004

  日期：2010.1

  oxide/TMEDA-catalyzed cross-coupling of vinyl halides with thiols/diphenyl diselenide in anhydrous DMSO and KOH is reported. Utilizing this protocol various vinyl sulfides and selenides were synthesized in excellent yields with retention of the stereochemistry. The catalyst was recyclable.

  据报道，在无水DMSO和KOH中，氧化镧/ TMEDA催化卤代乙烯与硫醇/二苯基二硒化物的交叉偶联。利用该方案，以优异的产率合成了各种乙烯基硫化物和硒化物，并保留了立体化学。该催化剂是可回收的。
• A facile approach to substituted acrylates by regioselective and stereoselective addition of thiols and amines to an alkynyl ester in water
  作者：Nitin A. Randive、Varun Kumar、Vipin A. Nair

  DOI：10.1007/s00706-010-0399-9

  日期：2010.12

  AbstractWater-promoted hydrothiolation and hydroamination of ethyl propiolate leading to highly regioselective and stereoselective formation of thioacrylates and β-enamino esters in excellent yields, by a simple, efficient, and environmentally friendly reaction procedure without employing any hazardous reagent or solvent is reported. Graphical Abstract

  摘要据报道，通过简单，有效且环保的反应程序，无需使用任何危险的试剂或溶剂，水促进的丙酸乙酯的加氢硫醇化和加氢胺化作用就可以以极高的收率实现高度区域选择性和立体选择性的硫代丙烯酸酯和β-烯氨基酯的形成。 图形概要
• Microwave-promoted regio- and stereoselective vinylation of heterocyclic thiols
  作者：Nimmakuri Rajesh、Rupam Sarma、Dipak Prajapati

  DOI：10.1039/c3ra47417h

  日期：——

  The first stereoselective vinylation of heterocyclic thiols has been reported. Heterocyclic thiols are shown to react efficiently with activated terminal alkynes in an anti-Markovnikov fashion in absence of any catalyst or additive under microwave irradiation to give Z-selective vinyl sulfides.

  首次报道了杂环硫醇的立体选择性乙烯基化反应。研究表明，在没有任何催化剂或添加剂的情况下，杂环硫醇可在微波辐照下与活化的末端炔以反马尔科夫尼科夫方式高效反应，生成 Z 选择性乙烯基硫化物。
• Efficient Copper-Catalyzed S-Vinylation of Thiols with Vinyl Halides
  作者：Hsin-Lun Kao、Chin-Fa Lee

  DOI：10.1021/ol2020863

  日期：2011.10.7

  The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couple with aryl iodides in the presence of only 0.5 mol % Cu2O without the need for an ancillary ligand. In the presence of 5 mol % of Cu2O and 10 mol % 1,10-phenanthroline as the ligand, the more challenging alkyl vinyl bromides can also be coupled with thiols, giving the vinyl sulfides in good to excellent yields.