N,N-diethyl-α-(phenylethynyl)-α-(3-pyridyl)-methanamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-diethyl-α-(phenylethynyl)-α-(3-pyridyl)-methanamine
• 英文别名: N,N-diethyl-3-phenyl-1-(pyridin-3-yl)prop-2-yn-1-amine；N,N-diethyl-3-phenyl-1-pyridin-3-ylprop-2-yn-1-amine
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: KTWYHCLOBAXYDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-diethyl-α-(methoxy)-α-(3-pyridyl)-methanamine 、 苯乙炔 在 indium(III) bromide 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.2h， 以65%的产率得到N,N-diethyl-α-(phenylethynyl)-α-(3-pyridyl)-methanamine
  参考文献：
  名称：

  Facile and convenient synthesis of functionalized propargylic alcohols and amines: an InBr3–Et3N reagent system promotes the alkynylation of aldehydes and N,O- or N,S-acetals

  摘要：

  The use of a novel InBr3-Et3N reagent system to promote the alkynylation of not only a variety of aromatic/heterocyclic or bulky aliphatic aldehydes but also N,O or N,S-acetals is described. The use of N-silyl-N,O-acetals and 1-alkynes could lead to the direct production of primary propargylic amines in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.059

文献信息

• Silver Nanoparticles Supported by Novel Nickel Metal-Organic Frameworks: An Efficient Heterogeneous Catalyst for an A³ Coupling Reaction
  作者：Lexin Song、Zhiyong Wang、Sujing Wang、Xiaoxiao He

  DOI：10.1055/s-0028-1087540

  日期：2009.2

  A novel heterogeneous catalyst of silver nanoparticles was prepared by using a nickel metal-organic framework (Ni-MOF) as a template. The catalyst has a very high catalytic activity and a strict structural selectivity towards linear aliphatic aldehydes in an A³ coupling reaction. The catalyst could be recovered by simple phase separation and reused for many times without obvious loss of activity.

  一种新型的银纳米粒子异质催化剂通过使用镍金属有机框架（Ni-MOF）作为模板制备。该催化剂在A³偶联反应中对线性脂肪醛具有非常高的催化活性和严格的结构选择性。催化剂可以通过简单的相分离进行回收，且多次重复使用后活性没有明显下降。
• Silver(I) complexes as efficient source for silver oxide nanoparticles with catalytic activity in A3 coupling reactions
  作者：Manoj Trivedi、Gurmeet Singh、Abhinav Kumar、Nigam P. Rath

  DOI：10.1016/j.ica.2015.09.025

  日期：2015.11

  New silver(I) complexes [Ag-7(mu(4)-Cl)(mu(3)-Cl)(2)(mu(2)-Cl)(3)(MPI)(6)] (1), and [Ag(mu(3)-I)(BI)](n) (2) [MPI = 1-(4-methoxyphenyl)- 1H-imidazole; BI = 1-Benzylimidazole] have been prepared starting with AgX (X = Cl, I) and 1-(4-methoxyphenyl)-1H-imidazole/1-Benzylimidazole. The complexes have been characterized by elemental analysis, IR, H-1 NMR, and electronic absorption spectroscopy. Molecular structure of the complexes 1 and 2 were determined crystallographically. Complex 1 has a twofold axis with Ag3 in special position and bisecting the Ag4-Ag4' vector. It contains six 1-(4-methoxyphenyl)-1H-imidazole molecules and seven chlorine atoms bridging the seven silver atoms. Complex 2 exists as a one-dimensional (1D) polymeric chain of [(mu(3)-I) Ag(mu(3)-I) Ag] fragments bridged via the 1-Benzylimidazole ligand. The weak argentophilic Ag center dot center dot center dot Ag interaction distances in complexes 1 and 2 are 3.1014(4) angstrom-3.2998(15) angstrom, respectively. The complexes 1 and 2, yielded silver oxide nanoparticles on pyrolysis and were characterized by PXRD and TEM. The catalytic properties of the resulting silver oxide nanoparticles and the silver(I) complexes have also been studied for A(3)-coupling of amines, alkynes and aldehydes in microwave which gave moderate to good yields of propargylamines. Silver(I) complexes exhibit higher catalytic activity compared to silver oxide nanoparticles. The silver oxide nanoparticles as well as silver(I) complexes could be separated easily from the reaction mixture and reused at least four to five times without significant loss of the catalytic activity. (C) 2015 Elsevier B.V. All rights reserved. 3
• Facile and convenient synthesis of functionalized propargylic alcohols and amines: an InBr3–Et3N reagent system promotes the alkynylation of aldehydes and N,O- or N,S-acetals
  作者：Norio Sakai、Reiko Kanada、Maki Hirasawa、Takeo Konakahara

  DOI：10.1016/j.tet.2005.07.059

  日期：2005.9

  The use of a novel InBr3-Et3N reagent system to promote the alkynylation of not only a variety of aromatic/heterocyclic or bulky aliphatic aldehydes but also N,O or N,S-acetals is described. The use of N-silyl-N,O-acetals and 1-alkynes could lead to the direct production of primary propargylic amines in good yields. (c) 2005 Elsevier Ltd. All rights reserved.