5-[(5-ethynyl-1-naphthyl)ethynyl]-N,N-dimethylnaphthalen-1-amine | 609355-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-[(5-ethynyl-1-naphthyl)ethynyl]-N,N-dimethylnaphthalen-1-amine
• 英文别名: 5-[2-(5-ethynylnaphthalen-1-yl)ethynyl]-N,N-dimethylnaphthalen-1-amine
• CAS: 609355-59-1
• 化学式: C₂₆H₁₉N
• 分子量: 345.444
• InChiKey: JJEWDIPOOFAOQW-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C
• 沸点：
  541.3±30.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  5-[(5-ethynyl-1-naphthyl)ethynyl]-N,N-dimethylnaphthalen-1-amine 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 50.0h， 生成 5-{[5-({5-[(5-{N,N-dimethylamino}-1-naphthyl)ethynyl]-1-naphthyl}ethynyl)-1-naphthyl]ethynyl}-N,N-dimethylnaphthalen-1-amine
  参考文献：
  名称：

  Synthesis of the end-capped 5-(N,N-dimethylamino)naphthyl-1-ethynyl derivatives and their 1,4-di[5-(N,N-dimethylamino)naphthyl]-1,3-butadiynes: anti rotamer structure

  摘要：

  A new family of the end-capped 5-(N,N-dimethylamino)naphthylethynyl chains were synthesized, as terminal acetylenes or poly(yne) structures, by heterocoupling between 5-iodo-N,N-dimethylnaphthalen-1-amine and 2-methyl-3-butyn-2-ol or 4-(5-iodo-1-naphthyl)-2-methyl-3-butyn-2-ol, catalyzed by the palladium-copper system. Catalytic homocoupling of the terminal acetylenes, affords to 1,4-dinaphthyl-1,3-butadiyne nanostructures. X-ray diffraction analysis of 1,4-di(alpha-naphthyl)-1,3-butadiyne shows that the naphthalene rings are in the anti configuration along the acetylene axis. All the conjugated compounds show an important fluorescent emission radiation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.109
• 作为产物：
  描述：

  5-iodo-N,N-dimethylnaphthalene-1-amine 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper (I) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 45.0h， 生成 5-[(5-ethynyl-1-naphthyl)ethynyl]-N,N-dimethylnaphthalen-1-amine
  参考文献：
  名称：

  基于线性 1,4-苯乙炔基或 1,5-萘乙炔基亚基中的封端 N,N-二甲氨基的 π 延伸共轭碳树突纳米链：荧光分析

  摘要：

  摘要 以 5-( N , N - 二甲基氨基) 萘基-1-乙炔基单元连接到共轭萘乙炔基或对苯乙炔基链，作为 1,3,5-取代苯核心的支链，合成树枝状化合物，在钯-铜催化剂存在下，通过 1,3,5-三碘苯与方便的封端 5-(N,N-二甲氨基)萘乙炔或 5-(N,N-二甲氨基)萘乙炔基苯乙炔之间的杂偶联反应进行系统，产量高。已经分析了交替的萘乙炔基-苯乙炔基链对树突结构中荧光发射辐射的影响。

  DOI：

  10.1016/j.tet.2004.12.054

文献信息

• Synthesis of carbon dendron nano-chains with π-extended conjugation based on linear 1,4-phenylethynyl and 1,5-naphthylethynyl subunits
  作者：J.Gonzalo Rodrı́guez、J.Luis Tejedor、Jorge Esquivias、Cristina Dı́az

  DOI：10.1016/s0040-4039(03)01615-0

  日期：2003.8

  A convenient and efficient synthesis of 3,5-di(trimethylsilylethynyl)phenylacetylene and p-[3,5-di(trimethylsilylethynyl)-1-phenylethynyl]phenylacetylene and the naphthylethynyl homologues terminal acetylenes of 5-(N,N-dimethylamino)naphthylethyne have been carried out. These terminal acetylene compounds serve to prepare nanometer-sized conjugated 1,3,5-tri(ethynylphenyl)benzene and 1,3,5-tri(ethynylnaphthyl)benzene

  3,5-二（三甲基甲硅烷基乙炔基）苯基乙炔和对-[3,5-二（三甲基甲硅烷基乙炔基）-1-苯基乙炔基]苯基乙炔和5-（N，N-二甲基氨基）萘乙炔的萘乙炔基同系物末端乙炔的简便有效合成已经进行了。这些末端乙炔化合物通过与1,3,5-三碘代苯催化杂化，用于制备纳米级的共轭1,3,5-三（乙炔基苯基）苯和1,3,5-三（乙炔基萘基）苯低聚物。由钯制成，收率极高。乙炔基苯基或乙炔基萘基同系物链均显示出荧光发射辐射，具有重要的量子产率。
• Synthesis of the end-capped 5-(N,N-dimethylamino)naphthyl-1-ethynyl derivatives and their 1,4-di[5-(N,N-dimethylamino)naphthyl]-1,3-butadiynes: anti rotamer structure
  作者：J. Gonzalo Rodríguez、J. Luis Tejedor

  DOI：10.1016/j.tet.2005.01.109

  日期：2005.3

  A new family of the end-capped 5-(N,N-dimethylamino)naphthylethynyl chains were synthesized, as terminal acetylenes or poly(yne) structures, by heterocoupling between 5-iodo-N,N-dimethylnaphthalen-1-amine and 2-methyl-3-butyn-2-ol or 4-(5-iodo-1-naphthyl)-2-methyl-3-butyn-2-ol, catalyzed by the palladium-copper system. Catalytic homocoupling of the terminal acetylenes, affords to 1,4-dinaphthyl-1,3-butadiyne nanostructures. X-ray diffraction analysis of 1,4-di(alpha-naphthyl)-1,3-butadiyne shows that the naphthalene rings are in the anti configuration along the acetylene axis. All the conjugated compounds show an important fluorescent emission radiation. (c) 2005 Elsevier Ltd. All rights reserved.
• Carbon dendron nano-chains with π-extended conjugation based on end-capped N,N-dimethylamino in linear 1,4-phenylethynyl or in 1,5-naphthylethynyl subunits: fluorescence analysis
  作者：J. Gonzalo Rodríguez、J. Luis Tejedor

  DOI：10.1016/j.tet.2004.12.054

  日期：2005.2

  Abstract The synthesis of dendrons with the end-capped 5-( N , N -dimethylamino)naphthyl-1-ethynyl unit connected to conjugated naphthylethynyl or p -phenylethynyl chains, as the branches of the 1,3,5-substituted benzene core, have been undertaken by heterocoupling reaction between 1,3,5-triiodobenzene and the convenient end-capped 5-( N , N -dimethylamino)naphthylacetylene or 5-( N , N -dimethyla

  摘要 以 5-( N , N - 二甲基氨基) 萘基-1-乙炔基单元连接到共轭萘乙炔基或对苯乙炔基链，作为 1,3,5-取代苯核心的支链，合成树枝状化合物，在钯-铜催化剂存在下，通过 1,3,5-三碘苯与方便的封端 5-(N,N-二甲氨基)萘乙炔或 5-(N,N-二甲氨基)萘乙炔基苯乙炔之间的杂偶联反应进行系统，产量高。已经分析了交替的萘乙炔基-苯乙炔基链对树突结构中荧光发射辐射的影响。