1-mesitylselanyl-2-phenylethyne | 123775-85-9

• 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: 1-mesitylselanyl-2-phenylethyne
• 英文别名: 1-(2,4,6-trimethylphenyl)seleno-2-phenylacetylene；(2,4,6-Me3C6H2)SeCCPh；1,3,5-Trimethyl-2-(2-phenylethynylselanyl)benzene
• CAS: 123775-85-9
• 化学式: C₁₇H₁₆Se
• 分子量: 299.274
• InChiKey: ACKGGTTUMKCBCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  dicobalt octacarbonyl 、 1-mesitylselanyl-2-phenylethyne 以 甲苯 、 正戊烷 为溶剂， 以95%的产率得到Co(CO)3Co(CO)3{(CH₃)3C₆H₂SeCC(C₆H₅)}
  参考文献：
  名称：

  Lang, Heinrich; Keller, Holger; Imhof, Wolfgang, Chemische Berichte, 1990, vol. 123, p. 417 - 422

  摘要：

  DOI：
• 作为产物：
  描述：

  mesitylselenolate lithium 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.5h， 生成 1-mesitylselanyl-2-phenylethyne
  参考文献：
  名称：

  Lang, Heinrich; Keller, Holger; Imhof, Wolfgang, Chemische Berichte, 1990, vol. 123, p. 417 - 422

  摘要：

  DOI：

文献信息

• A simple and stereoselective synthesis of (Z)-1,2-bis-arylselanyl alkenes from alkynes using KF/Al2O3
  作者：Renata G. Lara、Paloma C. Rosa、Liane K. Soares、Márcio S. Silva、Raquel G. Jacob、Gelson Perin

  DOI：10.1016/j.tet.2012.08.055

  日期：2012.12

  The title compounds were synthesized by a one-pot reaction of diaryl diselenides with terminal alkynes avoiding the previous preparation of arylselanyl alkynes. The reactions were performed under mild conditions with a range of terminal alkynes using KF/Al2O3 and PEG-400 as solvent. The addition of diaryl diselenides to alkynes occurred stereoselectively to give exclusively (Z)-1,2-bis-arylselanyl

  通过二芳基二硒化物与末端炔烃的一锅反应来合成标题化合物，从而避免了之前制备芳基硒基炔烃的情况。反应在温和条件下，使用KF / Al 2 O 3和PEG-400作为溶剂，在一定范围的末端炔烃下进行。立体选择性地将二芳基二硒化物加成至炔烃中，以良好的收率仅得到（Z）-1,2-双-芳基-杂戊基烯基烯烃。使用微波辐射将反应时间缩短至几分钟，并且KF / Al 2 O 3 / PEG-400系统可以重复使用一次，而无需事先进行类似活性的处理。
• 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。
• 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。
• Synthesis and reaction chemistry of [(μ-SeR)(μ-σ,π-CCPh)]Fe2(CO)6
  作者：D. Taher、H. Pritzkow、B. Walfort、H. Lang

  DOI：10.1016/j.jorganchem.2005.10.021

  日期：2006.2

  RSeC CPh (1a, R = Et; 1b, R = n-Bu; 1c, R = Ph; 1d, R = 2,4,6-Me3C6H2) reacts with equimolar amounts of Fe-2(CO)(9) (2) to give [(mu-SeR)(mu-sigma, pi-C CPh)]Fe-2(CO)(6) (3a, R = Et; 3b, R = n-Bu; 3c, R = Ph; 3d, R = 2,4,6-Me3C6H2). Complexes 3a 3d exist as two isomers, depending on the axial or equatorial position of R at selenium. Addition of P((OC3H7)-C-i)(3) (4) to 3d affords (mu-Se-2,4,6-Me3C6H,)[mu-eta(1) -C=CPh(P((OC3H7)-C-i)(3))]} Fel(CO)(6) (5) along with (mu-Se-2,4,6-Me3C6H2)[mu-eta(1):eta(1)- PhC=C(P((OC3H7)-C-i)(3))]} Fe-2(CO)(6) (6). The solid-state structures of 3d, 5 and 6 were determined by single X-ray structure analysis. In mononuclear 3d the Fe(CO)(3) fragments are bridged by a mu-Se-2,4,6-Me3C6H2 and a mu-sigma,pi-C CPh unit, resulting in an over-all butterfly arrangement.Due to steric reasons, the mesityl group is pointing away from the PhC C entity and hence, is located in an equatorial position.Compounds 5 and 6, which cocrystallise in the ratio of 7:93, feature a mu-bridging 2,4,6-Me3C6H2Se unit and either a vinylidenic C=CPh(P((OC3H7)-C-i)(3)) (complex 5) or a olefinic PhC=C(P((OC3H7)-C-i)(3)) (complex 6) building block of which the latter entity is part of a diiron cyclobutene ring. (c) 2005 Elsevier B.V. All rights reserved.
• Synthesis of (Z)-N-alkenyl-β-arylselanyl imidazoles via additive-free nucleophilic addition of imidazole to arylselanylalkynes
  作者：Liane K. Soares、Renata G. Lara、Raquel G. Jacob、Eder J. Lenardão、Diego Alves、Gelson Perin

  DOI：10.1016/j.tetlet.2013.12.058

  日期：2014.1

  We present herein our results on the nucleophilic addition of imidazole to a range of arylselanylalkynes by simple heating in DMF without any additives to give (Z)-1-(1-organyl-(2-arylselanyl)vinyl)-1H-imidazoles. The reactions were performed under mild conditions with a range of arylselanylalkynes in good yields and with high regio- and stereoselectivity to give the respective (Z)-arylselanyl alkene as the only isomer. (C) 2013 Elsevier Ltd. All rights reserved.