N,N-dibutyl-4-ethynyl-3-[(triisopropylsilyl)ethynyl]aniline | 547735-44-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dibutyl-4-ethynyl-3-[(triisopropylsilyl)ethynyl]aniline
• 英文别名: Benzenamine, N,N-dibutyl-4-ethynyl-3-[[tris(1-methylethyl)silyl]ethynyl]-；N,N-dibutyl-4-ethynyl-3-[2-tri(propan-2-yl)silylethynyl]aniline
• CAS: 547735-44-4
• 化学式: C₂₇H₄₃NSi
• 分子量: 409.731
• InChiKey: NNZJSRYLKVPECN-UHFFFAOYSA-N

物化性质

• 沸点：
  486.0±45.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 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-dibutyl-4-ethynyl-3-[(triisopropylsilyl)ethynyl]aniline 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 copper diacetate 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  让最好的戒指胜出：通过Pd催化或Cu介导的炔烃均偶联选择性形成大环。

  摘要：

  DOI：

  10.1002/anie.200353043
• 作为产物：
  描述：

  N,N-dibutyl-3-[(triisopropylsilyl)ethynyl]-4-[(trimethylsilyl)ethynyl]aniline 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以100%的产率得到N,N-dibutyl-4-ethynyl-3-[(triisopropylsilyl)ethynyl]aniline
  参考文献：
  名称：

  Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes

  摘要：

  A series of tetrakis(phenylethynyl)benzenes and bis(dehydrobenzoannuleno)benzenes have been synthesized containing tetra-substitutions of neutral, donor, and mixed donor/acceptor groups. To ascertain the importance of substitutional and structural differences of the phenylacetylenes, the optical absorption and emission properties of each series were examined. Conjugation effectiveness, electron density, planarity, and geometry of charge-transfer pathways were found to have a pronounced effect on the overall optical and material properties. Considerable self-association behavior due to face-to-face stacking in solution was observed for donor/acceptor-functionalized macrocycles and was quantified by concentration-dependent H-1 NMR measurements. A solvent-dependent polymerization of one macrocycle regioisomer was observed and characterized. To provide further insight into the energy levels and electronic transitions present, computational studies of each system were performed.

  DOI：

  10.1021/ja044175a

文献信息

• Molecular Folding of C60 Acetylenic Cyclophanes:  π-Stacking of Superimposed Aromatic Rings
  作者：Matthew A. Heuft、Shawn K. Collins、Alex G. Fallis

  DOI：10.1021/ol0345576

  日期：2003.5.1

  [GRAPHIC]The syntheses of two distinct families of phenylyne helical cyclophanes with potential for organic materials are described. The meta-bonded atropisomers afford interesting bowtie-like and butterfly-like conformers from a palladium(0), copper-mediated coupling sequence. Molecular modeling revealed the contrasting stereochemistry in these systems from differential molecular folding pathways during cyclization. The interplanar separation of the superimposed aromatic rings is similar to3.5 Angstrom.
• Structure−Property Relationships of Fluorinated Donor/Acceptor Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes
  作者：Eric L. Spitler、John M. Monson、Michael M. Haley

  DOI：10.1021/jo701740n

  日期：2008.3.1

  Nine new bisdonor/bisacceptor-functionalized tetrakis(phenylethynyl)benzene (TPEB) and six new bis(dehydrobenzoannuleno)benzene (DBA) chromophores have been synthesized. The compounds consist of electron-donating dibutylaniline groups connected through a conjugated phenyl -acetylene scaffold to benzotrifluoride, bis(trifluoromethyl)phenyl, or pentafluorophenyl acceptor groups. In comparison to previously reported analogues utilizing nitrophenyl or benzonitrile acceptor groups, the weaker acceptor groups exhibit visibly fluorescent intramolecular charge transfer (ICT) behavior, moderately narrow optical band gaps, moderately high quantum yields, and strong fluorescence solvatochromism. In this series of molecules, the strongly inductive fluoro acceptor groups result in optical properties similar to the resonance acceptor analogues, making them promising candidates for optical materials device components. The data also support recent investigations that question the utility of using UV/vis spectroscopy alone as a qualitative measure of conjugation. The bisDBAs exhibit weaker ICT behavior and self-association in solution than their corresponding nitro analogues, but show greater stability to decomposition via polymerization and smaller optical band gaps than their acyclic analogues.
• Structure−Property Relationships of Donor/Acceptor-Functionalized Tetrakis(phenylethynyl)benzenes and Bis(dehydrobenzoannuleno)benzenes
  作者：Jeremiah A. Marsden、Jeremie J. Miller、Laura D. Shirtcliff、Michael M. Haley

  DOI：10.1021/ja044175a

  日期：2005.3.1

  A series of tetrakis(phenylethynyl)benzenes and bis(dehydrobenzoannuleno)benzenes have been synthesized containing tetra-substitutions of neutral, donor, and mixed donor/acceptor groups. To ascertain the importance of substitutional and structural differences of the phenylacetylenes, the optical absorption and emission properties of each series were examined. Conjugation effectiveness, electron density, planarity, and geometry of charge-transfer pathways were found to have a pronounced effect on the overall optical and material properties. Considerable self-association behavior due to face-to-face stacking in solution was observed for donor/acceptor-functionalized macrocycles and was quantified by concentration-dependent H-1 NMR measurements. A solvent-dependent polymerization of one macrocycle regioisomer was observed and characterized. To provide further insight into the energy levels and electronic transitions present, computational studies of each system were performed.
• Let the Best Ring Win: Selective Macrocycle Formation through Pd-Catalyzed or Cu-Mediated Alkyne Homocoupling
  作者：Jeremiah A. Marsden、Jeremie J. Miller、Michael M. Haley

  DOI：10.1002/anie.200353043

  日期：2004.3.19