N,N-dimethyl-1-phenyl-5-(p-tolyl)penta-1,4-diyn-3-amine | 1233691-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-dimethyl-1-phenyl-5-(p-tolyl)penta-1,4-diyn-3-amine
• 英文别名: N,N-dimethyl-1-(4-methylphenyl)-5-phenylpenta-1,4-diyn-3-amine
• CAS: 1233691-41-2
• 化学式: C₂₀H₁₉N
• 分子量: 273.378
• InChiKey: PNVBSDTUZMGQOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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,N-dimethyl-1-phenyl-5-(p-tolyl)penta-1,4-diyn-3-amine 、 丁炔二酸二甲酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以93%的产率得到dimethyl (Z)-2-(3-(dimethylamino)-1-phenyl-5-p-tolylpenta-1,4-diyn-3-yl)maleate
  参考文献：
  名称：

  Copper-Catalyzed Coupling Reaction of C−OMe Bonds Adjacent to a Nitrogen Atom with Terminal Alkynes

  摘要：

  The cross coupling of the C-OMe bond adjacent to a nitrogen atom in dialkoxy-N,N-dialkylmethanamines with terminal alkynes was efficiently approached in the presence of copper catalyst under mild conditions to give 3-amino-1,4-diynes in good yields. The reaction is promoted by phosphine ligands and the chemistry provides a simple and efficient route to 3-amino-1,4-diynes. Importantly, the Michael addition occurred with as-prepared 3-amino-1,4-diynes to give the useful Michael-adducts containing tert-alkylamines in a very convenient way. Further studies revealed that (E)-1,5-diarylpent-1-en-4-yn-3-one was formed through the rearrangement by using the neutral alumina column, and the corresponding imine 2-(1,5-diphenylpent-2-en-4-ynylideneamino)ethanol was obtained in the presence of AgOTf.

  DOI：

  10.1021/jo1007898
• 作为产物：
  描述：

  对甲基苯乙酮 在 copper(l) iodide 、 三氟甲磺酸酐 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 N,N-dimethyl-1-phenyl-5-(p-tolyl)penta-1,4-diyn-3-amine
  参考文献：
  名称：

  通过Cu(I)-催化烯胺酮与末端炔烃的反应一锅法合成对称和不对称3-氨基二炔

  摘要：

  已经描述了通过烯胺酮和末端炔烃的 Cu (I) 催化反应直接构建氨基跳过二炔的经济有效的方案。通过在温和条件下的一锅反应，可以以高达 83% 的产率获得不同种类的对称和不对称 3-氨基二炔。

  DOI：

  10.1021/acs.orglett.1c02848

文献信息

• Ligand-free reusable nano copper oxide-catalyzed synthesis of 3-amino-1,4-diynes
  作者：Subhajit Mishra、Sougata Santra、Alakananda Hajra

  DOI：10.1039/c5ra18350b

  日期：——

  The synthesis of 3-amino-1,4-diynes has been developed by the two-component coupling of N,N-dimethyl formamide dimethyl acetal with terminal alkynes using CuO nanoparticles as an efficient catalyst under mild reaction conditions in ambient air. The procedure is applicable to aryl, alkyl, alkenyl, and heteroaryl alkynes. The CuO nanoparticles are easily recyclable without the loss of significant catalytic

  通过在环境空气中温和的反应条件下使用CuO纳米颗粒作为有效催化剂，通过N，N-二甲基甲酰胺二甲基乙缩醛与末端炔烃的两组分偶联，开发了3-氨基-1,4-二炔。该程序适用于芳基，烷基，烯基和杂芳基炔烃。CuO纳米颗粒易于回收，而不会损失明显的催化活性。
• One-Pot Synthesis of Symmetrical and Asymmetrical 3-Amino Diynes via Cu(I)-Catalyzed Reaction of Enaminones with Terminal Alkynes
  作者：Changyuan Zhang、Huosheng Guo、Lulu Chen、Jiantao Zhang、Mengping Guo、Xuncheng Zhu、Chan Shen、Zeng Li

  DOI：10.1021/acs.orglett.1c02848

  日期：2021.11.5

  economical and efficient protocol for the direct construction of amino skipped diynes through the Cu(I)-catalyzed reaction of enaminones and terminal alkynes has been described. Different kinds of symmetrical and asymmetrical 3-amino diynes could be obtained in up to 83% yield through a one-pot reaction under mild conditions.

  已经描述了通过烯胺酮和末端炔烃的 Cu (I) 催化反应直接构建氨基跳过二炔的经济有效的方案。通过在温和条件下的一锅反应，可以以高达 83% 的产率获得不同种类的对称和不对称 3-氨基二炔。
• Copper-Catalyzed Coupling Reaction of C−OMe Bonds Adjacent to a Nitrogen Atom with Terminal Alkynes
  作者：Bangben Yao、Yuhong Zhang、Yong Li

  DOI：10.1021/jo1007898

  日期：2010.7.2

  The cross coupling of the C-OMe bond adjacent to a nitrogen atom in dialkoxy-N,N-dialkylmethanamines with terminal alkynes was efficiently approached in the presence of copper catalyst under mild conditions to give 3-amino-1,4-diynes in good yields. The reaction is promoted by phosphine ligands and the chemistry provides a simple and efficient route to 3-amino-1,4-diynes. Importantly, the Michael addition occurred with as-prepared 3-amino-1,4-diynes to give the useful Michael-adducts containing tert-alkylamines in a very convenient way. Further studies revealed that (E)-1,5-diarylpent-1-en-4-yn-3-one was formed through the rearrangement by using the neutral alumina column, and the corresponding imine 2-(1,5-diphenylpent-2-en-4-ynylideneamino)ethanol was obtained in the presence of AgOTf.