3-((2-methoxyphenyl)ethynyl)pyridine | 1191900-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-((2-methoxyphenyl)ethynyl)pyridine
• 英文别名: 3-[(2-methoxyphenyl)ethynyl]pyridine
• CAS: 1191900-33-0
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: OXGVTUKGJIGWDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 3-((2-methoxyphenyl)ethynyl)pyridine 在 十二羰基三铁 、 氨 作用下， 以 四氢呋喃 为溶剂， 120.0 ℃ 、2.0 MPa 条件下， 反应 20.0h， 以70%的产率得到3-(2-methoxyphenyl)-4-(pyridin-3-yl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  高效合成具有生物意义的3,4-二芳基取代的琥珀酰亚胺和马来酰亚胺：铁催化羰基化的应用

  摘要：

  描述了通过钯催化的Sonogashira反应和铁催化的双羰基化反应的简单的两步法合成反式-3,4-二取代的琥珀酰亚胺。原位氧化脱氢得到相应的3,4-二芳基马来酰亚胺。通过从容易获得的芳基和杂芳基卤化物开始，可以良好的收率和选择性获得各种新的具有生物活性的3,4-双吲哚基马来酰亚胺的类似物和衍生物。

  DOI：

  10.1002/chem.201000369
• 作为产物：
  描述：

  3-溴吡啶 、 2-乙炔基苯甲醚 在 copper(l) iodide 、 potassium tetrachloropalladate(II) 、 四甲基乙二胺 、 2-二叔丁基膦-1-苯基吲哚 作用下， 反应 20.0h， 以99%的产率得到3-((2-methoxyphenyl)ethynyl)pyridine
  参考文献：
  名称：

  高效合成具有生物意义的3,4-二芳基取代的琥珀酰亚胺和马来酰亚胺：铁催化羰基化的应用

  摘要：

  描述了通过钯催化的Sonogashira反应和铁催化的双羰基化反应的简单的两步法合成反式-3,4-二取代的琥珀酰亚胺。原位氧化脱氢得到相应的3,4-二芳基马来酰亚胺。通过从容易获得的芳基和杂芳基卤化物开始，可以良好的收率和选择性获得各种新的具有生物活性的3,4-双吲哚基马来酰亚胺的类似物和衍生物。

  DOI：

  10.1002/chem.201000369

文献信息

• Mild Pd/Cu-Catalyzed Sila-Sonogashira Coupling of (Hetero)aryl Bromides with (Hetero)arylethynylsilanes under PTC Conditions
  作者：Fabio Bellina、Marco Lessi

  DOI：10.1055/s-0031-1290601

  日期：2012.3

  The palladium/copper cocatalyzed sila-Sonogashira reaction of (hetero)arylethynysilanes with (hetero)aryl bromides in toluene and water at 40 ˚C under PTC conditions gave the required di(hetero)arylethynes in moderate to high yields. Activated, deactivated and ortho-substituted (hetero)aryl bromides are well tolerated. This protocol also allowed the preparation of symmetrical diarylethynes by double

  在PTC条件下，在40°C的甲苯和水中，钯/铜共催化的（杂）芳基乙硅烷与（杂）芳基溴化物的钯/铜sila-Sonogashira反应可以中等至高收率得到所需的二（杂）芳基乙炔。活化，失活和邻位取代的（杂）芳基溴化物都具有良好的耐受性。该方案还允许通过1，2-双（三甲基甲硅烷基）乙炔的双芳基化制备对称的二芳基乙炔。 Sonogashira反应-钯-炔基硅烷-二芳基乙炔-铜-相转移催化
• 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.