4-(5-methyl-1-phenylhex-1-yn-3-yl)morpholine | 1208119-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(5-methyl-1-phenylhex-1-yn-3-yl)morpholine
• 英文别名: 4-(5-Methyl-1-phenylhex-1-yn-3-yl)morpholine
• CAS: 1208119-37-2
• 化学式: C₁₇H₂₃NO
• 分子量: 257.376
• InChiKey: MZFBERCYNJLFCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  异戊醛 在 disodium hydrogenphosphate 、 copper(l) chloride 、 copper(I) bromide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 72.0h， 生成 4-(5-methyl-1-phenylhex-1-yn-3-yl)morpholine
  参考文献：
  名称：

  Copper(I)-Catalysed Deacetylenative Cross-Coupling Reaction of Terminal Alkynes with Propargylic Amines via C(sp)-C(sp3) Bond Cleavage

  摘要：

  The catalytic deacetylenative coupling reaction of terminal alkynes with various N-substituted propargylic amines proceeded in the presence of CuCl (10 mol%) and Na2HPO4 (4 equiv) in THF at 130 degrees C to give the corresponding substituted propargylic amines in good to high yields.

  DOI：

  10.1055/s-0031-1290376

文献信息

• Nickel-Catalyzed Solvent-Free Three-Component Coupling of Aldehyde, Alkyne and Amine
  作者：Kayambu Namitharan、Kasi Pitchumani

  DOI：10.1002/ejoc.200901084

  日期：2010.1

  A versatile three-component coupling of aldehydes, alkynes and amines has been developed, catalyzed by Ni 2+ -exchanged Y-zeolite, which acts as an environmentally benign, recyclable, efficient and heterogeneous catalyst. This three-component (A 3 ) coupling (reported for the first time to proceed under nickel catalysis) is carried out under solvent-free conditions, and the corresponding propargylamines

  一种多功能的醛、炔和胺的三组分偶联已被开发出来，由 Ni 2+ 交换的 Y 沸石催化，它作为一种环境友好、可回收、高效和多相的催化剂。这种三组分（A 3 ）偶联（首次报道在镍催化下进行）是在无溶剂条件下进行的，相应的炔丙胺以良好到极好的收率获得。
• Copper(I)-Catalyzed Decarboxylative Coupling of Propiolic Acids with Secondary Amines and Aldehydes
  作者：Denis S. Ermolat'ev、Huangdi Feng、Gonghua Song、Erik V. Van der Eycken

  DOI：10.1002/ejoc.201402338

  日期：2014.8

  propargylamines has been developed by copper(I)-catalyzed decarboxylative A3-coupling reaction of an alkynylcarboxylic acid with a secondary amine and an aldehyde. A wide range of diversely substituted propargylamines could be synthesized in high yields. The optimal reaction conditions are also effective for 3-alkylpropiolic acids and for terminal propiolic acid.

  通过炔基羧酸与仲胺和醛的铜 (I) 催化脱羧 A3 偶联反应，开发了一种高效的微波辅助合成叔炔胺。可以高产率合成多种不同取代的炔丙胺。最佳反应条件对 3-烷基丙炔酸和末端丙炔酸也有效。
• Synthesis and characterization of magnetic glycocyamine-modified chitosan as a biosupport for the copper immobilization and its catalytic activity investigation
  作者：F. Rafiee、F. Rezaie Karder

  DOI：10.1016/j.reactfunctpolym.2019.104434

  日期：2020.1

  coordination. The magnetization of modified chitosan was done using of Fe3O4 nanoparticles. In the presence of coordinated groups of glycocyamine containing amidino and carboxylate, copper ions were immobilized on this magnetic biopolymer. This new nanocomposite (Fe3O4@CSC@AG@Cu) was characterized by FT-IR, FE-SEM, EDX, XRD, VSM, DRS and ICP analysis. After which, its catalytic activity was examined in the three

  摘要Trichloro-1,3,5-triazine试剂用于壳聚糖功能化，并作为功能化壳聚糖和糖胺之间的桥梁，形成铜配位的生物配体。改性壳聚糖的磁化是使用Fe3O4纳米粒子完成的。在含有glyco基和羧酸根的糖胺的配位基团的存在下，铜离子被固定在该磁性生物聚合物上。通过FT-IR，FE-SEM，EDX，XRD，VSM，DRS和ICP分析对这种新型纳米复合材料（ @ CSC @ AG @ Cu）进行了表征。此后，在脂族和芳族醛，仲环胺和苯基乙炔的三个偶联反应中，对炔丙基胺衍生物的合成进行了催化活性研究。
• Propargyl Amine Synthesis Catalysed by Gold and Copper Thin Films by Using Microwave-Assisted Continuous-Flow Organic Synthesis (MACOS)
  作者：Gjergji Shore、Woo-Jin Yoo、Chao-Jun Li、Michael G. Organ

  DOI：10.1002/chem.200902396

  日期：2010.1.4

  An effective multi‐component reaction (MCR) protocol has been developed for the construction of propargyl amines from aldehydes, amines and terminal alkynes by using microwave‐assisted continuous‐flow organic synthesis (MACOS). The process is catalysed by thin films of either copper or gold that achieve temperatures in excess of 900 °C when irradiated with low levels of microwave power. The process

  通过使用微波辅助连续流有机合成（MACOS），已开发出一种有效的多组分反应（MCR）方案，用于从醛，胺和末端炔烃构建炔丙基胺。该过程由铜或金的薄膜催化，当用低水平的微波功率照射时，其温度会超过900°C。该方法对于三种原料的预混合溶液或作为三个独立的料流同样有效，从而提高了该方法的组合效率。该工艺可耐受各种官能团和杂环，并且在这些不同的底物上的转化率范围为70-90％。
• Rapid one-pot propargylamine synthesis by plasmon mediated catalysis with gold nanoparticles on ZnO under ambient conditions
  作者：María González-Béjar、Kate Peters、Geniece L. Hallett-Tapley、Michel Grenier、Juan C. Scaiano

  DOI：10.1039/c3cc38287g

  日期：——

  Surface plasmon excitation of gold nanoparticles on ZnO in the presence of an aldehyde, an amine and phenylacetylene led to rapid and selective formation of propargylamines with good yields (50–95%) at room temperature. Plasmon mediated catalysis is the best available route for this ternary coupling.

  在一种醛、一种胺和苯乙炔的存在下，ZnO 上的金纳米粒子受到表面等离子激发，从而在室温下快速、有选择性地形成了丙炔胺，并获得了良好的产率（50-95%）。等离子体介导催化是实现这种三元偶联的最佳途径。