(Z)-2-(phenylseleno)-1-(phenylthio)-1-phenylethene | 1266317-72-9

• 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)-2-(phenylseleno)-1-(phenylthio)-1-phenylethene
• 英文别名: [(Z)-2-phenyl-2-phenylsulfanylethenyl]selanylbenzene
• CAS: 1266317-72-9
• 化学式: C₂₀H₁₆SSe
• 分子量: 367.373
• InChiKey: FNHYWLATABMFJD-SILNSSARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• 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

• 作为产物：
  描述：

  2-phenylethynyl phenyl selenide 、 二苯二硫醚 在 sodium tetrahydroborate 作用下， 以 PEG-400 为溶剂， 反应 3.5h， 以74%的产率得到(Z)-2-(phenylseleno)-1-(phenylthio)-1-phenylethene
  参考文献：
  名称：

  Highly stereoselective method to prepare bis-phenylchalcogen alkenes via addition of chalcogenolate to phenylseleno alkynes

  摘要：

  The preparation of bis-phenylchalcogen alkenes starting from phenylseleno alkynes is described. The nucleophilic species of selenium, tellurium and sulfur were generated in situ from the reaction of the respective diphenyl dichalcogenide with NaBH4 in PEG-400 as solvent. The chalcogenolate anions were efficiently and selectively added to a variety of phenylselenoalkynes at mild conditions, furnishing the respective (Z)-1,2-bis-phenylchalcogen alkenes in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.028

文献信息

• Cesium-Catalyzed Regioselective Synthesis of Trisubstituted Heteroatom Alkenes: A New Strategy for the Preparation of Functional Alkenes
  作者：Jinyang Chen、Zhi Tang、Renhua Qiu、Yunhua He、Xie Wang、Ningbo Li、Haibo Yi、Chak-Tong Au、Shuang-Feng Yin、Xinhua Xu

  DOI：10.1021/acs.orglett.5b00751

  日期：2015.5.1

  A highly chemo-, regio-, and stereoselective method for the synthesis of (Z)-vinylic selenosulfides and (Z)-vinylic tellurosulfides in a one-pot reaction of terminal alkynes, diaryl disulfides, and diaryl diselenides (ditellurides) catalyzed by simple base cesium hydroxide monohydrate is described. Due to the different activities of the carbon–chalcogen bonds, the target products cleave selectively

  一种高化学，区域和立体选择性的方法，可通过简单的催化在末端炔烃，二芳基二硫化物和二芳基二硒化物（ditellurides）的一锅反应中合成（Z）-乙烯基硒代硫化物和（Z）-乙烯基碲代硫化物描述了碱式氢氧化铯一水合物。由于碳-硫属元素键的活性不同，目标产物可选择性裂解并充当合成四取代烯烃的一种容易获得的平台分子。通过实验和理论方法研究了硫代硒化的机理。
• Cesium-catalyzed highly regioselective synthesis of (Z)-vinylic selenosulfides via thioselenation of alkynes with unsymmetrical diorganoyl dichalcogenides
  作者：Lifen Peng、Rongzhen Li、Zilong Tang、Jingyang Chen、Rongnan Yi、Xinhua Xu

  DOI：10.1016/j.tet.2017.04.009

  日期：2017.6

  A novel one-pot approach for the synthesis of (Z)-vinylic selenosulfides is demonstrated through the thioselenation of a wide range of alkynes with unsymmetrical diorganoyl dichalcogenides (RSSePh) catalyzed by cesium hydroxide monohydrate, avoiding the use of the transition metal catalyst and the previous preparation of chalcogen alkynes. Other outstanding features include mild reaction conditions

  一种新颖的一锅法合成（Z）-乙烯基硒代硫化物的方法是通过使用氢氧化铯一水合物催化的不对称二有机酰基二卤代二硫化物（RSSePh）催化广泛的炔烃进行硫代硒化反应，从而避免了使用过渡金属催化剂和硫属炔的先前制备。其他突出的特征包括温和的反应条件，高的区域和立体选择性，出色的收率和宽泛的官能团耐受性。
• Cesium hydroxide-catalyzed hydrothiolation of alkynyl selenides to highly stereo- and regioselectively synthesize (Z)-1-organoseleno-2-arylthio-1-alkenes
  作者：Ai He Yu、Ren Hua Qiu、Nian Yuan Tan、Li Feng Peng、Xin Hua Xu

  DOI：10.1016/j.cclet.2010.12.050

  日期：2011.6

  In the presence of catalytic amount of cesium hydroxide the hydrothiolation of alkynyl selenides occurred at room temperature in DMF under nitrogen atmosphere to give exclusive (Z)-1-organoseleno-2-arylthio-1-alkene in excellent yields. It could provide a new and expedient way for the preparation of (Z)-1-arylseleno-2-arylthio-1-alkene. (C) 2011 Xin Hua Xu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Highly stereoselective method to prepare bis-phenylchalcogen alkenes via addition of chalcogenolate to phenylseleno alkynes
  作者：Gelson Perin、Elton L. Borges、Diego Alves

  DOI：10.1016/j.tetlet.2012.02.028

  日期：2012.4

  The preparation of bis-phenylchalcogen alkenes starting from phenylseleno alkynes is described. The nucleophilic species of selenium, tellurium and sulfur were generated in situ from the reaction of the respective diphenyl dichalcogenide with NaBH4 in PEG-400 as solvent. The chalcogenolate anions were efficiently and selectively added to a variety of phenylselenoalkynes at mild conditions, furnishing the respective (Z)-1,2-bis-phenylchalcogen alkenes in good yields. (C) 2012 Elsevier Ltd. All rights reserved.