5-乙炔基异邻苯二甲醛 | 263746-70-9

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-乙炔基异邻苯二甲醛
• 英文名称: 5-Ethynylisophthalaldehyde
• 英文别名: 5-ethynylbenzene-1,3-dicarbaldehyde
• CAS: 263746-70-9
• 化学式: C₁₀H₆O₂
• 分子量: 158.156
• InChiKey: BYZDVHVYWADRID-UHFFFAOYSA-N

物化性质

• 沸点：
  307.8±37.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-乙炔基异邻苯二甲醛 在 盐酸 、 sodium periodate 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 25.17h， 生成 1,3-Bis(1-oxyl-4,4,5,5-tetramethylimidazolin-2-yl)-5-ethynylbenzene
  参考文献：
  名称：

  Towards a Better Understanding of the Magnetic Interactions withinm-Phenyleneα-Nitronyl Imino Nitroxide Based Biradicals

  摘要：

  An extensive investigation of the magnetic properties of three series of biradicals (bis-nitronyl nitroxides diNN-R, bis-imino nitroxides diIN-R and mixed INNN-R. where R is either hydrogen, a triple bond or trimethylsilylacetylenic group) has been carried out to give clear values of the intramolecular interactions through the m-phenylene coupling unit with alpha -nitronyl nitroxides (NN) or alpha -imino nitroxides (IN). An EPR study of the molecules in the isolated state is validated by ab initio calculations, which show the respective influence of spin polarisation and molecular conformation on the singlet-triplet gaps. All these results indicate that the triplet state is the ground state for such biradicals. except when the imidazolyl cycles are orthogonal to the phenyl ring. The magnetic properties of the biradicals in the solid state can be rationalised by examination of the short contacts produced between the ONC-NO and ONCN groups. EPR studies on single crystals of the H-substituted series have confirmed the presence of a structural distortion for diNN-H whereas diIN-H and INNN-H do not exhibit such a peculiarity. The magnetic behav lour of diIN-H is described well by a four-spins model, with a strong intermolecular antiferromagnetic interaction of -90 K, whereas in the case of the two other compounds. a supplementary contact involves more complex interactions between the dimers. The compound diNN-tmsa exhibits a ferromagnetic intermolecular interaction of +11 K within the dimers, and this could be attributed to the relative disposition of the imidazolyl rings. Compound diNN-tr reveals a chain-like behaviour, whereas diIN-tr shows a predominant antiferromagnetic interaction within the dimers. The values for the intramolecular interactions in the solid state are in good agreement with those found for the isolated molecules.

  DOI：

  10.1002/1521-3765(20010601)7:11<2466::aid-chem24660>3.0.co;2-4
• 作为产物：
  描述：

  间苯二甲酸 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 硼烷四氢呋喃络合物 、 硫酸 、 溴 、 potassium carbonate 、 silver sulfate 、 二异丙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 生成 5-乙炔基异邻苯二甲醛
  参考文献：
  名称：

  苯基乙炔基间隔基相互连接的硝酰基-和亚氨基-硝基氧化物-三基团的合成

  摘要：

  报道了基于带有乙氧基-亚硝基氧化物和亚氨基-亚硝基氧化物基团的苯基乙炔基骨架的三种新的三基自由基的设计，合成以及固态和ESR表征。这些化合物的合成是基于炔基和溴衍生物之间的钯偶联反应。一项ESR研究表明，自由基之间通过溶液中的乙炔基偶联单元发生了磁性相互作用。

  DOI：

  10.1016/s0040-4039(99)02218-2

文献信息

• Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy
  作者：Michael J. Strauss、Manping Jia、Austin M. Evans、Ioannina Castano、Rebecca L. Li、Xavier Aguilar-Enriquez、Emily K. Roesner、Jeremy L. Swartz、Anton D. Chavez、Alan E. Enciso、J. Fraser Stoddart、Marco Rolandi、William R. Dichtel

  DOI：10.1021/jacs.1c02789

  日期：2021.6.2

  with various aromatic dialdehydes yields chemically distinct pentagonal [5 + 5], hexagonal [3 + 3], and diamond-shaped [2 + 2] macrocycles depending on the substitution pattern of the aromatic dialdehyde monomer. Atomic force microscopy and in solvo X-ray diffraction demonstrate that protonation of the macrocycles under the mild conditions used for their synthesis drives assembly into high-aspect ratio

  组装成纳米管的大环由于其低维、结构规律和独特的内部环境而表现出新兴特性。我们报告了一种通用策略，通过使用带有吡啶环的保守构件，在单一、有效的反应中合成不同的纳米管结构。基于 2,4,6-三苯基吡啶的二胺与各种芳香族二醛的亚胺缩合产生化学上不同的五边形 [5 + 5]、六边形 [3 + 3] 和菱形 [2 + 2] 大环，具体取决于取代模式芳香族二醛单体。原子力显微镜和溶剂X 射线衍射表明，在用于合成的温和条件下，大环的质子化驱动组装成高纵横比的纳米管。通过电化学阻抗谱，每个含吡啶的纳米管组件都表现出可测量的质子电导率，其值高达 10 –3 S m –1（90% RH，25 °C），我们将其归因于它们内部孔径的差异。这种合成策略代表了一种从通用含吡啶单体中获取稳健纳米管组件的通用方法，这将使系统研究它们的新兴特性成为可能。
• Aromatic Schiff Bases Multiply Substituted with Terminal Ethynyl Groups: Potential Building Blocks for Conjugated Polymers and Oligomers
  作者：Sabina Stahlová、Jan Sedlácek、Jan Svoboda、Miroslav Polášek、Jirí Zedník

  DOI：10.1071/ch14639

  日期：——

  Nine mostly novel aromatic Schiff bases containing from two-to-four terminal ethynyl groups and one or two methanimine groups per one molecule are reported. The spectral and density functional theory characteristics and the extent of conjugation are discussed in connection with the structure and architecture of the prepared compounds. The applicability of compounds as building blocks for conjugated

  据报道，每一个分子含有九个大部分新颖的芳族席夫碱，每个席胺基具有2-4个末端乙炔基和一个或两个甲胺基。结合所制备化合物的结构和体系结构，讨论了光谱和密度泛函理论特性以及共轭程度。在TaCl 5催化的聚环三聚反应（乙炔基进行）中显示出化合物作为共轭聚合物的结构单元的适用性，从而产生可溶的发光或不溶的微孔聚合物。
• Synthesis of nitronyl- and imino-nitroxide-triradicals interconnected by phenyl ethynyl spacer
  作者：Laure Catala、Philippe Turek、Jacques Le Moigne、André De Cian、Nathalie Kyritsakas

  DOI：10.1016/s0040-4039(99)02218-2

  日期：2000.2

  The design and synthesis, as well as solid state and ESR characterisation of three new triradicals based on phenyl ethynyl backbone bearing nitronyl-nitroxide and imino-nitroxide groups, are reported. The synthesis of these compounds was based on palladium-coupling reactions between alkynyl and bromo derivatives. An ESR study showed magnetic interactions between the radicals through the phenyl ethynyl-coupling

  报道了基于带有乙氧基-亚硝基氧化物和亚氨基-亚硝基氧化物基团的苯基乙炔基骨架的三种新的三基自由基的设计，合成以及固态和ESR表征。这些化合物的合成是基于炔基和溴衍生物之间的钯偶联反应。一项ESR研究表明，自由基之间通过溶液中的乙炔基偶联单元发生了磁性相互作用。
• Towards a Better Understanding of the Magnetic Interactions withinm-Phenyleneα-Nitronyl Imino Nitroxide Based Biradicals
  作者：Laure Catala、Jacques Le Moigne、Nathalie Kyritsakas、Paul Rey、Juan J. Novoa、Philippe Turek

  DOI：10.1002/1521-3765(20010601)7:11<2466::aid-chem24660>3.0.co;2-4

  日期：2001.6.1

  An extensive investigation of the magnetic properties of three series of biradicals (bis-nitronyl nitroxides diNN-R, bis-imino nitroxides diIN-R and mixed INNN-R. where R is either hydrogen, a triple bond or trimethylsilylacetylenic group) has been carried out to give clear values of the intramolecular interactions through the m-phenylene coupling unit with alpha -nitronyl nitroxides (NN) or alpha -imino nitroxides (IN). An EPR study of the molecules in the isolated state is validated by ab initio calculations, which show the respective influence of spin polarisation and molecular conformation on the singlet-triplet gaps. All these results indicate that the triplet state is the ground state for such biradicals. except when the imidazolyl cycles are orthogonal to the phenyl ring. The magnetic properties of the biradicals in the solid state can be rationalised by examination of the short contacts produced between the ONC-NO and ONCN groups. EPR studies on single crystals of the H-substituted series have confirmed the presence of a structural distortion for diNN-H whereas diIN-H and INNN-H do not exhibit such a peculiarity. The magnetic behav lour of diIN-H is described well by a four-spins model, with a strong intermolecular antiferromagnetic interaction of -90 K, whereas in the case of the two other compounds. a supplementary contact involves more complex interactions between the dimers. The compound diNN-tmsa exhibits a ferromagnetic intermolecular interaction of +11 K within the dimers, and this could be attributed to the relative disposition of the imidazolyl rings. Compound diNN-tr reveals a chain-like behaviour, whereas diIN-tr shows a predominant antiferromagnetic interaction within the dimers. The values for the intramolecular interactions in the solid state are in good agreement with those found for the isolated molecules.