1-(4-chlorophenyl)seleno-2-phenylacetylene | 50991-47-4

• 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: 1-(4-chlorophenyl)seleno-2-phenylacetylene
• 英文别名: (4-chlorophenyl)(phenylethynyl)selane；p-Chlorphenyl-(2-phenylethinyl)-selenid；1-Chloro-4-(2-phenylethynylselanyl)benzene
• CAS: 50991-47-4
• 化学式: C₁₄H₉ClSe
• 分子量: 291.638
• InChiKey: RBWGIADBYUYLSR-UHFFFAOYSA-N

物化性质

• 沸点：
  379.7±44.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)seleno-2-phenylacetylene 、 丁炔二酸二乙酯 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以60%的产率得到tetraethyl 6-(4-chlorophenylselanyl)biphenyl-2,3,4,5-tetracarboxylate
  参考文献：
  名称：

  Palladium-catalyzed alkynylselenation of acetylenedicarboxylates leading to enyne selenides and application to synthesis of multisubstituted aryl selenides

  摘要：

  Upon treatment of a mixture of alkynyl selenides and acetylenedicarboxylates with Pd(OAc)(2)/P(o-tol)(3)/K2CO3/H2O-catalytic system, the alkynylselenation of acetylenedicarboxylates takes place to give the corresponding alkynylvinyl selenides. Furthermore, alkynyl selenides undergo the intermolecular [2+2+2] cycloaddition reaction in the presence of PdCl2(PPh3)(2) as a catalyst, affording the corresponding multisubstituted aryl selenides selectively.(C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.04.125
• 作为产物：
  描述：

  双(4-氯苯基)二硒化物 、 苯乙炔 在 copper(II) oxide 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 以75%的产率得到1-(4-chlorophenyl)seleno-2-phenylacetylene
  参考文献：
  名称：

  由可循环利用的氧化铜纳米粉催化的末端乙炔和二有机基二硒化物或二碲化物有效合成炔基硒化物和碲化物

  摘要：

  在这里，我们报告了一种有效的方法，可以使用CuO纳米粉作为可循环催化剂，从末端炔烃和二有机基二硒化物或二碲化物合成炔基硒化物和碲化物。这种新的方法以高至优异的产量提供了所需的产品。此外，该催化剂易于回收并重新用于进一步的催化反应而不会损失活性。

  DOI：

  10.1016/j.tet.2012.08.086

文献信息

• New arylselanylpyrazole-copper catalysts: Highly efficient catalytic system for C Se and C S coupling reactions
  作者：Felipe Lange Coelho、Lucielle Codeim Dresch、Rafael Stieler、Leandra Franciscato Campo、Paulo Henrique Schneider

  DOI：10.1016/j.catcom.2018.12.009

  日期：2019.3

  CSe and CS coupling reactions. The performance of these complexes for CSe reactions was investigated in chalcogenoacetylene synthesis. The reactions were carried out under mild and aerobic conditions and afforded selanylalkynes bearing a variety of electron-withdrawing and electron-donating groups. The performance of these catalysts for CS coupling was investigated through the reaction of aryl halides

  我们在本文中描述了芳基硒基吡唑-铜配合物作为C Se和C S偶联反应的通用催化剂的用途。在硫属乙炔的合成中研究了这些络合物对C Se反应的性能。反应在温和的需氧条件下进行，得到带有各种吸电子和给电子基团的硒代炔烃。通过芳基卤化物与硫醇的反应研究了这些催化剂的C S偶联性能，并以中等至极好的收率获得了产物。还提出了可能的硒代乙炔合成机理，并且77Se NMR结果表明，这些芳基硒基吡唑配体起半不稳定配体的作用。高分辨率质谱用于研究中间体，并证实所提出的催化循环。
• Alkynyl sulfides and selenides from alkynyl bromides and diorganoyl chalcogenides promoted by copper(I) iodide
  作者：Antonio L. Braga、Aurélia Reckziegel、Paulo H. Menezes、Hélio A. Stefani

  DOI：10.1016/0040-4039(93)85084-a

  日期：1993.1

  Alkynyl sulfides and selenides were obtained in good yields by reacting alkynyl bromides with diorganoyl disulfides and diselenides in hexamethylphosphoric triamide (HMPA) in the presence of copper (I) iodide.

  通过使炔基溴化物与二有机酰基二硫化物和二硒化物在六甲基磷酸三酰胺（HMPA）中在碘化铜（I）存在下反应，以高收率获得炔基硫化物和硒化物。
• Chalcogenoacetylenes Obtained by Indium(III) Catalysis: Dual Catalytic Activation of Diorgano Dichalcogenides and Csp-H Bonds
  作者：Daniel S. Rampon、Rodrigo Giovenardi、Tiago L. Silva、Raoní S. Rambo、Aloir A. Merlo、Paulo H. Schneider

  DOI：10.1002/ejoc.201101245

  日期：2011.12

  A new approach for the one-pot synthesis of alkynyl chalcogenides, exemplified mainly by selenides, was developed in which dual activation of diorgano dichalcogenides and terminal acetylenes is achieved by using an indium(III) catalyst. The method has advantages of broad substrate scope, simple operation, mild reaction conditions, and good yields. A plausible reaction mechanism is proposed.

  一种用于一锅法合成炔基硫属元素化物的新方法，主要以硒化物为例，该方法是通过使用铟 (III) 催化剂实现二有机二硫属元素化物和末端乙炔的双重活化而开发的。该方法具有底物范围广、操作简单、反应条件温和、收率高等优点。提出了一个合理的反应机制。
• An efficient and general procedure for the synthesis of alkynyl chalcogenides (selenides and tellurides) by alumina-supported Cu(II)-catalyzed reaction of alkynyl bromides and diphenyl dichalcogenides
  作者：Sabir Ahammed、Sukalyan Bhadra、Debasish Kundu、Bojja Sreedhar、Brindaban C. Ranu

  DOI：10.1016/j.tet.2012.08.046

  日期：2012.12

  catalyzes the reaction of alkynyl bromides and diphenyl diselenides and ditellurides in presence of Zn dust or indium(I) bromide to provide the corresponding alkynyl selenides and tellurides. The reactions of a wide variety of substituted alkynyl bromides have been addressed. The zinc dust or InBr is required for the cleavage of diphenyl selenides/tellurides. The mechanism of the reaction is established

  在锌粉或溴化铟（I）的存在下，氧化铝（Al 2 O 3）负载的铜（II）有效催化炔基溴化物与二苯基二硒化物和二碲化物的反应，从而提供相应的炔基硒化物和碲化物。已经解决了多种取代的炔基溴的反应。裂解二苯硒化物/碲化物需要锌粉或InBr。建立了反应机理。产品的产率很高，并且催化剂被回收。
• Cryptand-22 as an efficient ligand for the copper-catalyzed cross-coupling reaction of diorgano dichalcogenides with terminal alkynes leading to the synthesis of alkynyl chalcogenides
  作者：Elmira Mohammadi、Barahman Movassagh

  DOI：10.1016/j.tetlet.2014.01.088

  日期：2014.2

  A general and efficient method for the cross-coupling reaction of diorgano dichalcogenides with terminal alkynes using copper iodide/cryptand-22 (CuI/C22) has been developed. This protocol gave allcynyl chalcogenides in moderate to excellent yields in the presence of K3PO4 as the base under aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.