4-(1-(2-bromophenyl)-3-phenylprop-2-yn-1-yl)morpholine | 1174758-84-9

• 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: 4-(1-(2-bromophenyl)-3-phenylprop-2-yn-1-yl)morpholine
• 英文别名: 4-[1-(2-Bromophenyl)-3-phenylprop-2-ynyl]morpholine
• CAS: 1174758-84-9
• 化学式: C₁₉H₁₈BrNO
• 分子量: 356.262
• InChiKey: POOGYKHYXPJGEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吗啉 、 苯乙炔 、 邻溴苯甲醛 在 copper(l) iodide 、 丁二酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以99%的产率得到4-(1-(2-bromophenyl)-3-phenylprop-2-yn-1-yl)morpholine
  参考文献：
  名称：

  CuI催化的琥珀酸三组分偶联反应简单经济地合成炔丙胺

  摘要：

  开发了一种实用有效的方法，以CuI为催化剂，以琥珀酸为添加剂，通过一锅法从醛，胺和炔烃合成炔丙基胺。通过使用此协议，可以高收率获得各种炔丙基胺。

  DOI：

  10.1071/ch08086

文献信息

• Copper-based catalysts derived from salen-type ligands: synthesis of 5-substituted-1<i>H</i>-tetrazoles <i>via</i> [3+2] cycloaddition and propargylamines <i>via</i> A³-coupling reactions
  作者：Anshu Singh、Ankur Maji、Aurobinda Mohanty、Kaushik Ghosh

  DOI：10.1039/d0nj03081c

  日期：——

  spectroscopic studies. Molecular structures of complexes 1, 2 and 4 were determined by X-ray crystallography. Copper complexes (1-4) were employed as a catalyst for the [3+2] cycloaddition and A3 -coupling reactions. A mutual approach of salen-type ligands and metal via active participation of ligands allow to achieve the catalytic reactions. Reaction pathways were proposed and possible intermediate species

  由不对称席夫配体衍生的Salen型贱金属铜（II）配合物由配体L1H至L4H设计并合成，产率中等。合成的不对称配体L1H至L4H和相应的铜配合物（1-4）通过紫外可见，红外和ESI-MS光谱学研究表征。配合物1、2和4的分子结构通过X射线晶体学测定。铜配合物（1-4）被用作[3 + 2]环加成和A3-偶联反应的催化剂。萨伦型配体和金属通过配体的主动参与的共同方法可以实现催化反应。提出了反应途径，并通过ESI-MS光谱研究成功表征了催化循环中可能存在的中间物种。
• Copper(<scp>ii</scp>) carboxymethylcellulose (CMC-Cu^II) as an efficient catalyst for aldehyde–alkyne–amine coupling under solvent-free conditions
  作者：Xiaoping Liu、Bijin Lin、Zhuan Zhang、Hao Lei、Yiqun Li

  DOI：10.1039/c6ra18742k

  日期：——

  three-component reaction of aldehydes, amines, and alkynes (A3 coupling) catalyzed by a recoverable copper(II) carboxymethylcellulose (CMC-CuII) catalyst has been developed, producing a diverse range of propargylamines under solvent-free conditions in good yields. The CMC-CuII catalyzed reaction is especially effective for reactions involving aromatic and aliphatic aldehydes. High catalytic activity was obtained

  已开发出一种可回收的铜（II）羧甲基纤维素（CMC-Cu II）催化的醛，胺和炔烃的三组分新型环保反应（A3偶联），可在溶剂-自由条件下产量高。CMC-Cu II催化的反应对于涉及芳族和脂族醛的反应特别有效。在好氧条件下，在没有任何其他助催化剂，添加剂或碱的情况下，在5摩尔％CMC-Cu II的存在下获得了高催化活性。而且，该催化剂可以容易地回收和再利用至少四个循环而不会显着降低其催化活性。
• Cu0NPs@CMC: an efficient recoverable nanocatalyst for decarboxylative A3 and A3 couplings under neat condition
  作者：Xiaoping Liu、Xiaobin Tan、Yuemin Zhou、Yiqun Li、Zhubao Zhang

  DOI：10.1007/s11164-019-03795-3

  日期：2019.6

  Copper nanoparticles assembled on carboxymethylcellulose (Cu0NPs@CMC) were successfully synthesized and well characterized by FT-IR, SEM, EDS, TEM, XPS, and ICP-AES. The new prepared nanocatalyst was applied effectively as a heterogeneous catalyst for the synthesis of propargylamines via decarboxylatived A3 and classic A3 reaction under solvent-free condition. A broad spectrum of diversely polysubstituted propargylamines could be obtained in moderate to excellent yields. The present method showed several merits such as easy work-up, short reaction time, additive-free characteristic, solvent-free condition, functional group tolerance, usage of recyclable green and sustainable nanocatalyst.

  成功合成了组装在羧甲基纤维素上的铜纳米颗粒（Cu0NPs@CMC），并通过傅立叶变换红外光谱、扫描电子显微镜、电致发光分析、电子显微镜、XPS 和 ICP-AES 对其进行了表征。所制备的新型纳米催化剂作为一种异相催化剂，可在无溶剂条件下通过脱羧 A3 和经典 A3 反应合成丙炔胺。在中等到极好的产率下，可以获得多种多取代的丙炔胺。该方法具有操作简便、反应时间短、无添加剂、无溶剂、官能团耐受性强、使用可回收的绿色可持续纳米催化剂等优点。
• Copper-catalyzed one-pot synthesis of propargylamines via CH activation in PEG
  作者：Qiang Zhang、Jiu-Xi Chen、Wen-Xia Gao、Jin-Chang Ding、Hua-Yue Wu

  DOI：10.1002/aoc.1707

  日期：2010.11

  An efficient and convenient three‐component A3 coupling reaction of aldehyde, amine and alkyne via CH activation with CuI alone as the catalyst in PEG is developed, providing a wide range of propargylamines with yields ranging from moderate to excellent. Additionally, the catalyst system was recovered and reused several times without evident loss in activity. Copyright © 2010 John Wiley & Sons, Ltd

  开发了一种高效，便捷的醛，胺和炔烃通过CH活化的三组分A 3偶联反应，并单独使用CuI作为PEG中的催化剂，从而提供了各种炔丙基胺，收率从中到优。另外，催化剂体系被回收并重复使用了几次，而活性没有明显损失。版权所有©2010 John Wiley＆Sons，Ltd.
• Heterogeneous Copper Nanocatalyst and Manufacturing Methods Thereof
  申请人：Park Jai Wook

  公开号：US20110172417A1

  公开（公告）日：2011-07-14

  This invention relates to a heterogeneous copper nanocatalyst composed of copper nanoparticles immobilized on a boehmite support, a method of preparing the same, and the use thereof. The copper nanocatalyst composed of the copper nanoparticles supported on boehmite exhibits excellent performance in a Huisgen cycloaddition reaction and an A3 coupling reaction of aldehyde, amine and alkyne. The copper nanocatalyst is able to be prepared in a large scale and shows superior reactivity even when used in a small amount under mild conditions without an additive in an organic reaction. This heterogeneous catalyst is easy to separate and reuse after the reaction.

  本发明涉及一种异质铜纳米催化剂，由铜纳米颗粒固定在氧化铝支撑物上组成，以及其制备方法和使用方法。铜纳米颗粒支撑在氧化铝上的铜纳米催化剂在Huisgen环加成反应和醛、胺和炔的A3偶联反应中表现出优异的性能。铜纳米催化剂能够在大规模下制备，并且即使在有机反应中在温和条件下无添加剂时，使用少量也表现出优异的反应活性。这种异质催化剂易于在反应后分离和重复使用。