N-(1,3-diphenyl-2-propynyl)-N-methylaniline

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(1,3-diphenyl-2-propynyl)-N-methylaniline
• 英文别名: N-(1,3-diphenylprop-2-ynyl)-N-methylaniline
• 化学式: C₂₂H₁₉N
• 分子量: 297.4
• InChiKey: DQFVVWJHANRFNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (Benzotriazol-1-yl-phenyl-methyl)-methyl-phenyl-amine 、 Sodium;diethyl-bis(2-phenylethynyl)alumanuide 以 甲苯 为溶剂， 反应 3.0h， 以78%的产率得到N-(1,3-diphenyl-2-propynyl)-N-methylaniline
  参考文献：
  名称：

  A New Method of Synthesis for Propargylic Amines and Ethers via Benzotriazole Derivatives Using Sodium Dialkynyldiethylaluminates

  摘要：

  1-(alpha-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from Lithium acetylide. The reaction of alpha-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.

  DOI：

  10.1021/jo9814750

文献信息

• Solvent‐free synthesis of propargylamines via A ³ coupling reaction and organic pollutant degradation in aqueous condition using Cu/C catalyst
  作者：Pramod V. Rathod、John Marc C. Puguan、Hern Kim

  DOI：10.1002/aoc.5986

  日期：2020.12

  on the efficient and operationally simple synthesis of biomass‐derived carbon as support to immobilize copper particles as a catalyst for the one‐pot synthesis of propargylamines from furfural via the A3 coupling reaction. This new catalyst showed remarkable catalytic performance leading to a 97% yield within 5 h at 80 °C using 5 mg (0.0022 mmol Cu) of Cu/C catalyst under solvent‐free condition. Moreover

  本报告着重于高效且操作简单的合成生物质衍生碳作为载体，以固定铜颗粒作为催化剂，通过A 3从糠醛一锅合成炔丙基胺。偶联反应。这种新型催化剂表现出了出色的催化性能，在无溶剂条件下使用5 mg（0.0022 mmol Cu）的Cu / C催化剂在80°C下5h内收率达97％。此外，硝基取代的化合物（例如4-硝基苯酚（4-NP））剧毒且不易降解。因此，需要一种快速有效的方法来中和这些有毒化合物。合成的具有各种电子给体基团且含有少量Cu的活性载体Cu / C催化剂在4-NP（0.1 g）的催化还原中起着至关重要的作用。仅使用3 mg（0.0013 mmol Cu）的Cu / C催化剂和NaBH 4（10mmol），在25℃的水性条件下获得99％的收率（100％的选择性）。催化还原遵循拟一级动力学，反应速率常数为0.028 s -1。此外，结果表明，由于存在电子给体分子（例如O，S和N原子），Cu /
• A novel tetramer copper(I) complex containing diallylphosphine ligands: Synthesis, characterization and catalytic application in A3-coupling (Aldehyde-Amine-Alkyne) reactions
  作者：Jennifer Rosales、Juan M. Garcia、Edward Ávila、Teresa González、David Santiago Coll、Edgar Ocando-Mavárez

  DOI：10.1016/j.ica.2017.07.038

  日期：2017.10

  observed dynamic equilibrium in solution. The use of copper(I) complex 2 as catalyst for the synthesis of propargylamines via A3-coupling reactions has been tested. Complex 2 is capable of promoting A3-coupling reactions of both aromatic and aliphatic aldehydes with cyclic secondary amines and phenylacetylene. The reaction proceeds under mild condition and absence of solvent.

  摘要合成了一种新型的含叔丁基二烯丙基膦配体[CuCl tBu-P（ CH = CH2）2}] 4（2）的四聚铜（I）配合物，并通过结构和光谱方法对其进行了表征。X射线衍射分析表明，2具有像式[CuCl κ1（P）-tBu-P（ CH = ）2}] 4的类古巴固体结构。在溶液中，通过可变温度NMR分析检测了由古巴⇄椅异构化产生的动力学行为。已进行DFT计算以解释溶液中观察到的动态平衡。已经测试了使用铜（I）配合物2作为经由A 3偶联反应合成炔丙胺的催化剂。配合物2能够促进芳族和脂族醛与环状仲胺和苯乙炔的A 3偶联反应。
• Copper(I)-N₂ S₂ -salen type complex covalently anchored onto MCM-41 silica: an efficient and reusable catalyst for the A³ -coupling reaction toward propargylamines
  作者：Hossein Naeimi、Mohsen Moradian

  DOI：10.1002/aoc.2976

  日期：2013.5

  The immobilization of copper complexes by covalent anchoring of the ligand on the surface of mesoporous MCM‐41 has been described. Bis[2‐(phenylthio)benzylidene]‐1,2‐ethylenediamine as a new N2S2 donor salen‐type ligand was covalently anchored onto nanopores of MCM‐41 coordinated with copper (I) halide. The organic–inorganic hybrid material was achieved readily using 3‐mercaptopropyltrimethoxysilane

  已经描述了通过将配体共价锚定在介孔MCM-41表面上来固定铜络合物的方法。作为新的N 2 S 2供体salen型配体的双[2-（苯硫基）亚苄基] -1，2-乙二胺共价锚定在MCM-41的纳米孔上，并与卤化铜（I）配合使用。使用3-巯基丙基三甲氧基硅烷作为反应性表面改性剂可以轻松实现有机-无机杂化材料。2-硝基苯甲醛与硫醇基团平稳反应，以形成具有甲醛基的官能化纳米多孔二氧化硅。将得到的负载的有机部分转化为硫代沙仑配体并与CuX配位（X ＝ CN，Cl，Br，I）。通过X射线衍射N 2表征多相催化剂吸附，傅立叶变换红外光谱，漫反射紫外可见光和TGA技术表明成功将MCM-41纳米通道内的铜络合物接枝。通过醛，胺和炔烃的曼尼希缩合反应评估了异相催化剂。在该反应中，以良好至优异的产率获得了相应的炔丙基胺作为单一产物。还讨论了反应温度，溶剂，催化剂负载量，催化剂的浸出和可重复使用性等因素。使用MCM-
• Highly efficient three-component (aldehyde–alkyne–amine) coupling reactions catalyzed by a reusable PS-supported NHC–Ag(I) under solvent-free reaction conditions
  作者：Pinhua Li、Lei Wang、Yicheng Zhang、Min Wang

  DOI：10.1016/j.tetlet.2008.09.026

  日期：2008.11

  The development of a highly efficient, polystyrene-supported NHC–Ag(I) catalyst for the three-component coupling reactions of aldehydes, alkynes, and amines (A3-coupling) was described. In the presence of PS–NHC–Ag(I) (2 mol %), the A3-reactions were carried out at room temperature under solvent-free reaction conditions and the corresponding propargylamines were generated in good to excellent yields

  描述了一种高效的，聚苯乙烯负载的NHC - Ag（I）催化剂的开发，该催化剂用于醛，炔烃和胺的三组分偶联反应（A 3偶联）。在PS – NHC – Ag（I）（2 mol％）的存在下，A 3-反应在室温下在无溶剂的条件下进行，生成的相应炔丙基胺的收率非常好。此外，该催化剂可以重复使用至少12次，而不会显着降低其催化活性。
• An efficient and facile one-pot synthesis of propargylamines by three-component coupling of aldehydes, amines, and alkynes via C–H activation catalyzed by NiCl2
  作者：Subhasis Samai、Ganesh Chandra Nandi、M.S. Singh

  DOI：10.1016/j.tetlet.2010.08.043

  日期：2010.10

  NiCl2 was found to be a highly efficient and effective catalyst for the one-pot three-component (A3) coupling of aldehydes, amines, and alkynes to produce propargylamines in nearly quantitative yields. Structurally divergent aldehydes, amines, and alkynes were converted into the corresponding propargylamines. No co-catalyst or activator is needed and water is the only byproduct of this novel protocol.

  发现NiCl 2是用于醛，胺和炔的一锅三组分（A 3）偶联以几乎定量的产率生产炔丙基胺的高效和有效的催化剂。结构上不同的醛，胺和炔烃转化为相应的炔丙基胺。不需要助催化剂或活化剂，并且水是该新颖方案的唯一副产物。