2-((2,6-dimethylphenyl)ethynyl)-6-methoxynaphthalene | 1191900-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((2,6-dimethylphenyl)ethynyl)-6-methoxynaphthalene
• 英文别名: 2-[(2,6-dimethylphenyl)ethynyl]-6-methoxynaphthalene；2-[2-(2,6-Dimethylphenyl)ethynyl]-6-methoxynaphthalene；2-[2-(2,6-dimethylphenyl)ethynyl]-6-methoxynaphthalene
• CAS: 1191900-23-8
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: KUXIVPBSRRFRBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,3-二甲基-2-碘苯 、 2-乙炔基-6-甲氧基萘 在 potassium phosphate 、 C₂₈H₄₇ClN₄P₂Pd 作用下， 以 1,4-二氧六环 、 乙二醇 为溶剂， 反应 1.5h， 以66%的产率得到2-((2,6-dimethylphenyl)ethynyl)-6-methoxynaphthalene
  参考文献：
  名称：

  在无添加剂和无胺的条件下进行的基于氨基膦基钯的钳形配合物促进的高度便捷，清洁，快速和可靠的Sonogashira偶联反应

  摘要：

  Abstractmagnified imageSequential addition of 1,1′,1′′‐phosphinetriyltripiperidine and 1,3‐diaminobenzene or resorcinol to toluene solutions of (cyclooctadiene)palladium dichloride [Pd(cod)(Cl)2] under nitrogen in “one pot” almost quantitatively yielded the aminophosphine‐based pincer complexes {[C6H3‐2,6‐(XP{piperidinyl}2)2]Pd(Cl)} (X=NH 1; X=O 2). Complex 1 (and to a minor extent 2) proved to be efficient Sonogashira catalysts, which allow the quantitative coupling of various electronically deactivated and/or sterically hindered and functionalized aryl iodides and aryl bromides with several alkynes as coupling partners within very short reaction times and low catalyst loadings. Importantly, in contrast to most of the Sonogashira catalysts, which either are both air‐ and moisture‐sensitive and/or require the addition of co‐catalysts, such as copper(I) iodide [CuI], for example, or a large excess of an amine, the coupling reactions were carried out without the use of amines, co‐catalysts or other aditives and without exclusion of air and moisture. Moreover, the desired products were exclusively formed (no side‐products were detected) without employing an excess of one of the substrates. Ethylene glycol and potassium phosphate (K3PO4) were found to be the ideal solvent and base for this transformation. Experimental observations strongly indicate that palladium nanoparticles are not the catalytically active form of 1 and 2. On the other hand, their transformation into another homogeneous catalytically active species cannot be excluded.

  DOI：

  10.1002/adsc.200900112

文献信息

• Transition-Metal-Free Sonogashira-Type Coupling of <i>ortho</i>-Substituted Aryl and Alkynyl Grignard Reagents by Using 2,2,6,6-Tetramethylpiperidine-<i>N</i>-oxyl Radical as an Oxidant
  作者：Modhu Sudan Maji、Sandip Murarka、Armido Studer

  DOI：10.1021/ol1015702

  日期：2010.9.3

  Cross coupling of aryl, alkenyl, and alkynyl magnesium compounds by using 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO) as an environmentally benign organic oxidant is described. This coupling reaction can be performed without adding any transition metal on various ortho-substituted aryl and alkynyl Grignard reagents. Importantly, functional groups such as esters, amides, and cyanides are shown

  描述了通过使用2,2,6,6-四甲基哌啶-N-氧基自由基（TEMPO）作为对环境有益的有机氧化剂，对芳基，烯基和炔基镁化合物进行交叉偶联。可以在各种邻位取代的芳基和炔基格利雅试剂上不添加任何过渡金属的情况下进行该偶联反应。重要的是，显示出在反应条件下可以容忍酯，酰胺和氰化物等官能团。
• Highly Convenient, Clean, Fast, and Reliable Sonogashira Coupling Reactions Promoted by Aminophosphine-Based Pincer Complexes of Palladium Performed under Additive- and Amine-Free Reaction Conditions
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/adsc.200900112

  日期：2009.4

  Abstractmagnified imageSequential addition of 1,1′,1′′‐phosphinetriyltripiperidine and 1,3‐diaminobenzene or resorcinol to toluene solutions of (cyclooctadiene)palladium dichloride [Pd(cod)(Cl)2] under nitrogen in “one pot” almost quantitatively yielded the aminophosphine‐based pincer complexes [C6H3‐2,6‐(XPpiperidinyl}2)2]Pd(Cl)} (X=NH 1; X=O 2). Complex 1 (and to a minor extent 2) proved to be efficient Sonogashira catalysts, which allow the quantitative coupling of various electronically deactivated and/or sterically hindered and functionalized aryl iodides and aryl bromides with several alkynes as coupling partners within very short reaction times and low catalyst loadings. Importantly, in contrast to most of the Sonogashira catalysts, which either are both air‐ and moisture‐sensitive and/or require the addition of co‐catalysts, such as copper(I) iodide [CuI], for example, or a large excess of an amine, the coupling reactions were carried out without the use of amines, co‐catalysts or other aditives and without exclusion of air and moisture. Moreover, the desired products were exclusively formed (no side‐products were detected) without employing an excess of one of the substrates. Ethylene glycol and potassium phosphate (K3PO4) were found to be the ideal solvent and base for this transformation. Experimental observations strongly indicate that palladium nanoparticles are not the catalytically active form of 1 and 2. On the other hand, their transformation into another homogeneous catalytically active species cannot be excluded.