4-(1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-yl)morpholine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-yl)morpholine
• 英文别名: 4-(1-Naphthalen-2-yl-3-phenylprop-2-ynyl)morpholine；4-(1-naphthalen-2-yl-3-phenylprop-2-ynyl)morpholine
• 化学式: C₂₃H₂₁NO
• 分子量: 327.426
• InChiKey: CPLUBJZFYYBFNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-yl)morpholine 、 N-氟代双苯磺酰胺 在 indium(III) chloride 、 水 、 sodium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以90%的产率得到(E)-N-(3-(naphthalen-2-yl)-3-oxo-1-phenylprop-1-en-1-yl)-N-(phenylsulfonyl)benzenesulfonamide
  参考文献：
  名称：

  Divergent Synthesis of Allenylsulfonamide and Enaminonesulfonamide via In(III)-Catalyzed Couplings of Propargylamine and N-Fluorobenzenesulfonimide

  摘要：

  An In(III)-catalyzed facile and controllable method for the synthesis of allenylsulfonamide and enaminonesulfonamide has been achieved by the reaction between propargylamine and N-fluorobenzenesulfonimide (NFSI) under mild conditions. The present protocol is also applicable to the synthesis of tetrasubstituted allenylsulfonamide from triphenyl propargylalcohol. Experimental results suggest that the reaction probably proceeds through the ionic pathway.

  DOI：

  10.1021/acs.joc.8b01882
• 作为产物：
  描述：

  吗啉 、 2-萘甲醛 、 苯乙炔 在 silver⁽⁰⁾ nanoparticles grafted on the surface of porous organic polymer 作用下， 以 neat (no solvent) 为溶剂， 反应 12.0h， 以79%的产率得到4-(1-(naphthalen-2-yl)-3-phenylprop-2-yn-1-yl)morpholine
  参考文献：
  名称：

  Ag纳米粒子接枝多孔有机聚合物作为无溶剂A3偶联反应的高效多相催化剂

  摘要：

  新型C C/C N/C低成本催化体系设计O键形成反应在合成有机化学中非常具有挑战性。在此，我们通过在 POP 材料 PDVTA-1 的表面接枝银纳米颗粒，报道了一种新的 Ag NPs 固定多孔有机聚合物 (POP) 材料 Ag-NPs@PDVTA-1。PDVTA-1 是在溶剂热反应条件下通过二乙烯基苯和三烯丙基胺的自由基共聚合成的。PDVTA-1 以及载银催化剂 Ag-NPs@PDVTA-1 已经过充分表征以了解它们的物理化学性质。Ag-NPs@PDVTA-1 用作多相纳米催化剂，用于醛、仲胺和末端炔烃的一锅三组分 A3 偶联反应，在温和且环保的反应条件下合成多种炔丙基胺衍生物。在优化的反应条件下，在这种环境安全的催化剂上以高产率获得了所需的产物。Ag-NPs@PDVTA-1 的高比表面积 (694 m2 g -1 ) 及其在纳米结构中的高度可及的催化活性Ag 位点可能使其成为有效的催化剂

  DOI：

  10.1016/j.mcat.2022.112686

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。
• Preparation of Propargyl Amines in a ZnCl2–Dimethylurea Deep-Eutectic Solvent
  作者：Martin Obst、Akriti Srivastava、Sundarababu Baskaran、Burkhard König

  DOI：10.1055/s-0036-1588571

  日期：2018.1

  The coupling of an aldehyde, an amine, and an alkyne to yield propargyl amines was performed in a deep-eutectic solvent composed of zinc chloride and dimethylurea. The deep-eutectic solvent acts simultaneously as catalyst and solvent giving access to a variety of propargyl amines, which were isolated in moderate to very good yields.

  在由氯化锌和二甲基脲组成的低共熔溶剂中进行醛、胺和炔烃的偶联以产生炔丙基胺。深共熔溶剂同时充当催化剂和溶剂，从而获得各种炔丙基胺，这些炔丙基胺以中等至非常好的产率分离。
• Choline chloride‐urea deep eutectic solvent as an efficient media for the synthesis of propargylamines via organocuprate intermediate
  作者：Bahareh Abtahi、Hossein Tavakol

  DOI：10.1002/aoc.5895

  日期：2020.11

  A facile method for the synthesis of various propargylamines derivatives with different structural parts has been reported. The reaction has consisted of one‐pot coupling between aldehydes, secondary amines and terminal alkynes using CuCl as a catalyst and choline chloride/urea DES as a cheap and biocompatible reaction media. The procedure is free of using toxic solvents and used CuCl as an available

  已经报道了一种容易的合成具有不同结构部分的炔丙基胺衍生物的方法。该反应由醛，仲胺和末端炔烃之间的一锅耦合组成，使用CuCl作为催化剂，氯化胆碱/脲DES作为廉价且生物相容的反应介质。该过程无需使用有毒溶剂，而将CuCl用作可用的，廉价且无毒的催化剂。使用这种方法，可以在60°C下于15小时内成功合成15种不同的炔丙基胺衍生物，其中大多数收率很高。
• Study on the A3-coupling reaction catalyzed by readily available copper-containing minerals. Synthesis of propargylamines
  作者：Mátyás Milen、Gábor Györke、András Dancsó、Balázs Volk

  DOI：10.1016/j.tetlet.2019.151544

  日期：2020.3

  The highly atom efficient three-component reaction of aldehydes, secondary amines and acetylenes to form propargylamines (A(3)-coupling) has been studied with twelve readily available copper-containing minerals. It was found that the reaction could easily be performed in the presence of malachite, brochantite, chrysocolla and azurite in toluene at reflux. The desired products were obtained in good to excellent yields. (C) 2019 Elsevier Ltd. All rights reserved.
• Zn(OAc)2·2H2O: a versatile catalyst for the one-pot synthesis of propargylamines
  作者：Enugala Ramu、Ravi Varala、Nuvula Sreelatha、Srinivas R. Adapa

  DOI：10.1016/j.tetlet.2007.07.196

  日期：2007.10

  An inexpensive and readily available catalyst, Zn(OAc)(2)center dot 2H(2)O is successfully evaluated for effective one-pot synthesis of propargylamines with moderate to excellent yields for most of the substrates screened, without the need of base, co-catalyst or additive in the presence of air. (C) 2007 Elsevier Ltd. All rights reserved.