[(1,3-diphenyl)prop-2-ynyl]diisopropylamine

• 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: [(1,3-diphenyl)prop-2-ynyl]diisopropylamine
• 英文别名: N,N-diisopropyl-1,3-diphenylprop-2-yn-1-amine；N-(1,3-diphenyl-2-propynyl)diisopropylamine；1,3-diphenyl-N,N-di(propan-2-yl)prop-2-yn-1-amine
• 化学式: C₂₁H₂₅N
• 分子量: 291.436
• InChiKey: NSKUNGAIRGTPDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  二异己基酮 、 苯乙炔 在 bis(triphenylphosphine)iridium(I) carbonyl chloride 、 copper(I) bromide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以67%的产率得到[(1,3-diphenyl)prop-2-ynyl]diisopropylamine
  参考文献：
  名称：

  Ir和Cu（I）双金属顺序催化三级酰胺的化学选择性还原烷基化

  摘要：

  我们在这里报道了一种方便和通用的方法，用于通过顺序的Ir催化的氢化硅烷化反应-Cu（I）催化的炔基化反应，将叔酰胺直接还原性炔基化以生成炔丙基胺。反应进行中...

  DOI：

  10.1039/c6cc05318a

文献信息

• Manganese(<scp>ii</scp>) chloride catalyzed highly efficient one-pot synthesis of propargylamines and fused triazoles via three-component coupling reaction under solvent-free condition
  作者：Shakil N. Afraj、Chinpiao Chen、Gene-Hsian Lee

  DOI：10.1039/c4ra03232b

  日期：——

  A one-pot green and highly efficient method for the synthesis of propargylamines and diastereoselective synthesis of fused triazoles via three-component coupling in the presence of manganese(II) chloride as a catalyst and a catalyst-free 1,3-dipolar cycloaddition reaction, respectively, without using a co-catalyst or activator is reported. This methodology is efficient, eco-friendly, operationally

  一锅绿色高效的炔丙胺合成和稠合三唑的非对映选择性合成方法，该方法在氯化锰（II）作为催化剂和无催化剂的1,3-偶极环加成反应下，通过三组分偶联进行，分别报道了不使用助催化剂或活化剂的情况。这种方法对于涉及芳族，脂族和杂环醛的反应而言是高效，环保的，操作简单且有效的，并且可以轻松获得高产率的炔丙基胺，高产率的熔融三唑和非对映选择性。
• Copper nanoparticles supported on silica coated maghemite as versatile, magnetically recoverable and reusable catalyst for alkyne coupling and cycloaddition reactions
  作者：F. Nador、M.A. Volpe、F. Alonso、A. Feldhoff、A. Kirschning、G. Radivoy

  DOI：10.1016/j.apcata.2013.01.023

  日期：2013.3

  presented. The catalyst has been prepared under mild conditions by fast reduction of anhydrous CuCl2 with lithium sand and a catalytic amount of DTBB (4,4’-di-tert-butylbiphenyl) as electron carrier, in the presence of the magnetic support. The catalyst has been fully characterized and its performance in different coupling and cycloaddition reactions of terminal alkynes has been studied. This new copper-based

  在硅胶上涂布磁赤铁矿纳米颗粒（MagSilica由铜纳米粒子的多功能和磁性可恢复催化剂®）被呈现。该催化剂已通过快速还原无水氯化亚铜的温和条件下制备2用砂锂和DTBB催化量（4,4'-二-叔-丁基联苯）作为电子载体，在磁性载体存在下。该催化剂已被充分表征，并研究了其在末端炔烃的不同偶联和环加成反应中的性能。这种新型的铜基催化剂在无溶剂条件下的THF的Glaser炔二聚反应，水中的多组分Huisgen 1,3-偶极环加成反应以及炔丙基胺的三组分合成中已显示出非常高效且易于重用的特性。
• 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。
• Microwave-Promoted Three-Component Coupling of Aldehyde, Alkyne, and Amine via C−H Activation Catalyzed by Copper in Water
  作者：Lei Shi、Yong-Qiang Tu、Min Wang、Fu-Min Zhang、Chun-An Fan

  DOI：10.1021/ol049936t

  日期：2004.3.1

  [reaction: see text] An efficient three-component coupling of aldehyde, alkyne, and amine to generate propargylamines has been effected under microwave irradiation in water using only CuI catalyst without the noble metal cocatalyst. This method has proved to be applicable to a wide range of substrates. In addition, the preliminary experiment using (S)-proline methyl ester as a chiral source demonstrated

  [反应：见正文]在水中仅使用CuI催化剂而不使用贵金属助催化剂的情况下，在微波辐射下在水中进行了醛，炔烃和胺的有效三组分偶联以生成炔丙基胺。事实证明，该方法适用于多种基材。此外，使用（S）-脯氨酸甲酯作为手性来源的初步实验表明，它可以发展成为一种直接，高度非对映选择性的手性炔丙基胺的构建方法。
• Efficient multicomponent synthesis of propargylamines catalyzed by Cu(I) complexes encompassing hydrazone ligands under solvent-free condition
  作者：Sekar Gayathri、Periasamy Viswanathamurthi、Jan Grzegorz Malecki

  DOI：10.1016/j.ica.2022.120853

  日期：2022.5

  were utilized as reusable homogeneous catalysts in A3 coupling reactions involving aldehydes, amines and phenyl acetylene for the synthesis of propargylamines under solvent-free conditions. Particularly, complex 2 has been found to be highly efficient in the synthesis of propargylamines. Many novel compounds have been synthesized based on A3 coupling reaction and the formation of new compounds was confirmed

  [Cu(PPh 3 ) 2 (CH 3 COO)] 与腙反应合成了一系列具有 [Cu(PPh 3 ) 2 (L)] ( 1 – 3 )类型腙配体的铜 (I) 配合物配体 (L 1 - 3 ) [L 1  = 2-(oxoacenaphthylen-1, 2-ylidene)benzohydrazone ( BHy-BIAN ), L 2  = 2-(oxoacenaphthylen-1, 2-ylidene)thiophene-2-carbohydrazone ( FHy -BIAN ) 和 L 3  = 2-(oxoacenaphthylen-1,2-ylidene)isoicotinohydrazone ( NHy-BIAN）。通过微观分析和光谱（IR、UV-Vis、 1 H 和13 C NMR、ESI 质量和单晶 XRD）研究表征了合成复合物的形成。具体来说，固态结构研究证明了铜原子