N,N-dimethyl-1,5-di(thiophen-3-yl)penta-1,4-diyn-3-amine | 1233691-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N,N-dimethyl-1,5-di(thiophen-3-yl)penta-1,4-diyn-3-amine
• CAS: 1233691-32-1
• 化学式: C₁₅H₁₃NS₂
• 分子量: 271.407
• InChiKey: RRPDAKWLAWCANE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 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：
  59.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-1,5-di(thiophen-3-yl)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80%的产率得到dimethyl (Z)-2-(3-(dimethylamino)-1,5-di(thiophen-3-yl)penta-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：

  3-乙炔基噻吩 、 N,N-二甲基甲酰胺二甲基缩醛 在 copper(II) oxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以90%的产率得到N,N-dimethyl-1,5-di(thiophen-3-yl)penta-1,4-diyn-3-amine
  参考文献：
  名称：

  无配体的可重复使用的纳米氧化铜催化的3-amino-1,4-diynes合成†

  摘要：

  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。

  DOI：

  10.1039/c5ra18350b

文献信息

• 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.
• 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。