(E)-1,2-bis<(p-methylphenyl)seleno>styrene | 137568-61-7

• 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)-1,2-bis<(p-methylphenyl)seleno>styrene
• 英文别名: (E)-1-phenyl-1,2-bis(4-methylphenylseleno)ethene；(1-phenylethene-1,2-diyl)bis(p-tolylselane)；1-methyl-4-[(E)-2-(4-methylphenyl)selanyl-1-phenylethenyl]selanylbenzene
• CAS: 137568-61-7
• 化学式: C₂₂H₂₀Se₂
• 分子量: 442.321
• InChiKey: YTWWYWMZLKBDEX-CJLVFECKSA-N

物化性质

• 沸点：
  502.4±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  di-p-tolyl diselenide 、 苯乙炔 以 二氯甲烷 为溶剂， 反应 12.0h， 以71%的产率得到(E)-1,2-bis<(p-methylphenyl)seleno>styrene
  参考文献：
  名称：

  可见光促进炔烃的立体选择性芳基杂戊基官能化

  摘要：

  在这项工作中，使用普通荧光灯发出的可见白光作为能源，在没有催化剂或添加剂的情况下，合成了一系列的双芳基杂戊基戊烯基烯烃。通过自由基加成-光异构化，以非常干净和快速的方式获得了产物，得到了具有良好立体选择性的E-烯烃。

  DOI：

  10.1002/ejoc.201801303

文献信息

• Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes
  作者：Hitoshi Kuniyasu、Akiya Ogawa、Shinichiro Miyazaki、Ilhyong Ryu、Nobuaki Kambe、Noboru Sonoda

  DOI：10.1021/ja00026a013

  日期：1991.12

  Novel transition-metal-catalyzed reactions of disulfides and diselenides with acetylenes are described. In the of tetrakis(triphenylphosphine)palladium(0), [Pd(PPh3)4], the (1) of diaryl disulfides and diselenides to terminal acetylenes 1 takes place stereoselectively to give high yields of (Z)-1,2-bis(arylthio)-1-alkenes 2 and (Z)-1,2-bis(arylseleno)-1-alkenes 3, respectively. A mechanistic proposal includes the following: (1) oxidative addition of (ArY)2 [Y = S, Se] to low-valent palladium species, (2) stereoselective cis-thiopalladation or cis-selenopalladation to acetylenes to form a cis-vinylpalladium intermediate, and (3) reductive elimination of the product with retention of the stereochemistry. When the reaction of diaryl disulfides and diselenides with terminal acetylenes is performed under the pressure of carbon monoxide, the carbonylative addition occurs to afford (Z)-1,3-bis(arylthio)-2-alken-1-ones 4 and (Z)-1,3-bis(arylseleno)-2-alken-1-ones 5, respectively. Carbon monoxide is regioselectively incorporated on the side of the terminal carbon of the acetylenes.
• DES as a green solvent to prepare 1,2-bis-organylseleno alkenes. Scope and limitations
  作者：Eric F. Lopes、Lóren C. Gonçalves、Julio C.G. Vinueza、Raquel G. Jacob、Gelson Perin、Claudio Santi、Eder J. Lenardão

  DOI：10.1016/j.tetlet.2015.10.095

  日期：2015.12

  We describe here our results on the use of choline chloride/urea 1:2 as a deep eutectic solvent (DES) in the synthesis of vinyl selenides. A good selectivity for the (E)-1,2-bis-organylseleno alkenes was observed starting from terminal alkynes and diaryl or dibutyl diselenides in the presence of NaBH4. The reaction of 1,3-butadiynes with diphenyl diselenide afforded exclusively the respective mono-selenylated (Z)-alkenynes. Diphenyl ditelluride reacted with phenylacetylene and 1,4-diphenyl-but-1-en-3-yne affording (Z)-phenyltelluro alkenes in good yields. (C) 2015 Elsevier Ltd. All rights reserved.
• Addition of chalcogenolate anions to terminal alkynes using microwave and solvent-free conditions: easy access to bis-organochalcogen alkenes
  作者：Gelson Perin、Raquel G. Jacob、Luiz G. Dutra、Francisco de Azambuja、Greice F.F. dos Santos、Eder J. Lenardão

  DOI：10.1016/j.tetlet.2005.11.158

  日期：2006.2

  We present here the reaction of diphenyl dichalcogenides (Se and Te) with propargyl alcohols using alumina supported sodium borohydride under solvent-free conditions. This efficient and improved method is general and furnishes the corresponding vinyl chalcogenide preferentially with a Z configuration. We also observed that when the same protocol was applied to phenyl acetylene, the (E)-bis-organochalcogen alkenes were obtained in good yields and high selectivity. The use of MW irradiation facilitates the procedure and accelerates the reaction. (c) 2005 Elsevier Ltd. All rights reserved.