N-allyl-N-(1,3-diphenylprop-2-yn-1-yl)prop-2-en-1-amine | 499775-83-6

• 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: N-allyl-N-(1,3-diphenylprop-2-yn-1-yl)prop-2-en-1-amine
• 英文别名: 1,3-diphenyl-N,N-bis(prop-2-enyl)prop-2-yn-1-amine
• CAS: 499775-83-6
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: CEKUHBCTAMJDAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(1,3-diphenylprop-2-yn-1-yl)prop-2-en-1-amine 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 盐酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 72.0h， 生成 1,3-diphenylprop-2-yn-1-amine
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Fluoroalkenes by Directed Au(I) Catalysis

  摘要：

  Au-catalyzed hydrofluorination reactions of a range of functionalized alkynes are reported. In the presence of an appropriate directing group, localized with particular spacing from the pendant alkyne, regioselective and predictable conversion of the alkyne to the Z-vinyl fluoride may be achieved, In selected cases, yields and selectivities are excellent. Additional experiments with two directing groups installed have established some initial principles with respect to a hierarchy of directing groups and their capacity for influencing hydrofluorination regioselectivity.

  DOI：

  10.1021/ol9016782
• 作为产物：
  描述：

  苯乙酮 在 吡啶 、 selenium(IV) oxide 作用下， 以 neat (no solvent) 为溶剂， 反应 21.0h， 生成 N-allyl-N-(1,3-diphenylprop-2-yn-1-yl)prop-2-en-1-amine
  参考文献：
  名称：

  一维Fe3O4 @ CuSiO3复合材料催化脱羧A3-偶联制炔丙胺

  摘要：

  摘要通过磁诱导斯托伯法并随后在碱性条件下与铜离子发生水热反应，成功制备了高活性和稳定的磁性铜催化剂。所制备的催化剂中高含量的Cu 2+以及分层的硅酸铜独特的结构使其具有出色的催化性能。在低Fe3O4 @ CuSiO3负载下，实现了α-酮酸，胺和炔烃的高效脱羧A3偶联。在无溶剂条件下，可以生产出各种炔丙基胺，收率好至极好。而且，可以容易地用外部磁体将催化剂与最终的有机产物分离。同样，这种催化剂可以循环使用六次，同时保持其活性。

  DOI：

  10.1016/j.cclet.2019.11.004

文献信息

• Mannich Reactions of Alkynes: Mechanistic Insights and the Role of Sub-Stoichiometric Amounts of Alkynylcopper(I) Compounds in the Catalytic Cycle
  作者：Benjamin R. Buckley、Amna N. Khan、Harry Heaney

  DOI：10.1002/chem.201103987

  日期：2012.3.26

  alkynylcopper(I) compounds observed in the three‐component Mannich reactions of alkynes, secondary amines and aldehydes are shown to be pre‐catalysts that give rise to catalytic copper(I) alkyne complexes by interaction with secondary amines (see scheme). Interaction of these complexes with iminium ions (formed from aldehydes or their equivalents, including CH2Cl2), results in the formation of Mannich bases

  在炔烃，仲胺和醛的三组分曼尼希反应中观察到的黄色聚合炔铜（I）化合物显示为预催化剂，可通过与仲胺相互作用而生成催化铜（I）炔配合物（参见方案）。这些络合物与亚胺离子（由醛或它们的等价物，包括CH 2 Cl 2形成）相互作用，导致形成曼尼希碱，收率很高。
• Tertiary amine and method for producing the same
  申请人：——

  公开号：US20040260124A1

  公开（公告）日：2004-12-23

  The present invention relates to a method for easily producing a tertiary amine with high yield. A tertiary amine represented by general formula (1) is produced by adding a metal-containing reagent represented by general formula (6) into a reaction system consisting of thioamide represented by general formula (4), a methylating agent represented by general formula (5) and a solvent, and then adding thereto a Grignard reagent represented by general formula (7). 1 CH 3 —X  (5) R 8 -M 1 (6) R 7 -M 2 (7)

  这项发明涉及一种易于高产率生产三级胺的方法。通过将通式（6）表示的含金属试剂加入由通式（4）表示的硫代酰胺、通式（5）表示的甲基化试剂和溶剂组成的反应体系中，然后加入通式（7）表示的格氏试剂，生产通式（1）表示的三级胺。
• Ag2CO3-catalyzed efficient synthesis of internal or terminal propargylicamines and chalcones via A3-coupling under solvent-free condition
  作者：Ningbo Li、Shitang Xu、Xueyan Wang、Li Xu、Jie Qiao、Zhiwu Liang、Xinhua Xu

  DOI：10.1016/j.cclet.2021.04.026

  日期：2021.12

  or terminal propargylamines and chalcones via A3-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag2CO3 under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated

  几个简单，快速和实用的协议已被开发来合成内部或末端炔丙胺和查耳酮通过甲3 -耦合醛，胺的反应，和炔由容易获得的催化剂催化的Ag 2 CO 3无溶剂条件下进行。反应进行得很顺利，以良好的收率和良好的官能团耐受性提供了各种产品。已经证明了克级制备，生物活性分子合成和不对称底物。此外，已经提出了合成不同产物的合理机制。
• An efficient synthesis of propargylamines via C–H activation catalyzed by copper(<scp>i</scp>) in ionic liquids
  作者：Soon Bong Park、Howard Alper

  DOI：10.1039/b416268d

  日期：——

  A readily available copper(I) catalyst, in an ionic liquid, can effect three-component coupling of aldehydes, amines and alkynes to generate propargylamines in high yields.

  一种 readily available （易得的）铜(I) 催化剂，使用离子液体，可以实现醛、胺和炔烃的三组分耦合，生成高产率的丙炔胺。
• Semiconductor-Gold Nanocomposite Catalysts for the Efficient Three-Component Coupling of Aldehyde, Amine and Alkyne in Water
  作者：Leng Leng Chng、Jun Yang、Yifeng Wei、Jackie Y. Ying

  DOI：10.1002/adsc.200900518

  日期：2009.11

  An efficient heterogeneous lead sulfide-gold catalyst has been successfully developed for the synthesis of propargylic amines via a three-component coupling reaction of aldehyde, amine and alkyne in water. The process is simple and applicable to a diverse range of aromatic and aliphatic aldehydes, amines and alkynes. Furthermore, the catalyst is stable to air and water, and can be easily recovered

  通过醛，胺和炔在水中的三组分偶联反应，已成功开发了一种高效的多相硫化铅金催化剂，用于合成炔丙基胺。该方法很简单，适用于各种芳香族和脂肪族醛，胺和炔烃。此外，该催化剂对空气和水是稳定的，并且可以容易地回收和再利用。