4-叔丁基-2-乙炔基苯甲醛 | 1010447-02-5

• 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: 4-叔丁基-2-乙炔基苯甲醛
• 英文名称: 4-tert-butyl-2-ethynylbenzaldehyde
• 英文别名: 4-t-butyl-2-ethynylbenzaldehyde；4-Tert-butyl-2-ethynylbenzaldehyde
• CAS: 1010447-02-5
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: KJVVNVWVQVFLGY-UHFFFAOYSA-N

物化性质

• 沸点：
  288.6±40.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-叔丁基-2-乙炔基苯甲醛 、 1-碘芘 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 反应 7.0h， 以1.01 g的产率得到4-t-butyl-2-(1-pyrenylethynyl)benzaldehyde
  参考文献：
  名称：

  Conformational Isomers from Rotation of Diacetylenic Bond in an Ethynylpyrene-Substituted Molecular Hinge

  摘要：

  The first example of isolation and X-ray crystallographic structural characterization of two conformers arising from rotation along a diacetylenic bond is reported. In both the conformers extensive pi-pi interactions are observed in the solid state. VT-NMR and fluorescence spectroscopic studies in solution suggest that the closed and open conformers are in equilibrium and that the closed conformer is the predominant species at room temperature.

  DOI：

  10.1021/jo7024724
• 作为产物：
  描述：

  4-t-butyl-2-trimethylsilylethynylbenzaldehyde 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-叔丁基-2-乙炔基苯甲醛
  参考文献：
  名称：

  Conformational Isomers from Rotation of Diacetylenic Bond in an Ethynylpyrene-Substituted Molecular Hinge

  摘要：

  The first example of isolation and X-ray crystallographic structural characterization of two conformers arising from rotation along a diacetylenic bond is reported. In both the conformers extensive pi-pi interactions are observed in the solid state. VT-NMR and fluorescence spectroscopic studies in solution suggest that the closed and open conformers are in equilibrium and that the closed conformer is the predominant species at room temperature.

  DOI：

  10.1021/jo7024724

文献信息

• Unusual fluorescene emission from ethynyltriphenylene-substituted diacetylenic molecular hinge. Formation of intramolecular excimer
  作者：Ritesh Nandy、Sethuraman Sankararaman

  DOI：10.1039/b923441a

  日期：——

  A diacetylenic molecular hinge bearing two ethynyltriphenylene units (1) has been synthesized. Evidence from 1H NMR and variable temperature NMR (VT-NMR) of 1 in comparison to model compounds bearing only one triphenylene unit suggests that there is an equilibrium between the open conformer and the intramolecularly π–π interacting closed conformer in solution (equilibrium constant K = 6.5 at 298 K in CDCl3) arising from the rotation of the diacetylenic hinge. Unusual fluorescence emission observed from 1 has been assigned to excimer formation arising from intramolecularly π–π interacting triphenylene units in the excited state. Steady state and picosecond time resolved fluorescence spectra of 1 were nearly identical and corresponded to intramolecular excimer emission.

  合成了带有两个乙炔基苯并菲单元 (1) 的二乙炔分子铰链。 1 的 1 H NMR 和变温 NMR (VT-NMR) 与仅含有一个苯并菲单元的模型化合物相比的证据表明，溶液中开放构象异构体和分子内 π-π 相互作用的闭合构象异构体之间存在平衡（平衡常数 K = 6.5 at 298 K in CDCl3) 由二乙炔铰链的旋转产生。从 1 观察到的异常荧光发射被归因于激发态下分子内 π-π 相互作用的苯并菲单元形成准分子。 1 的稳态和皮秒时间分辨荧光光谱几乎相同并且对应于分子内准分子发射。
• US20150263297A1
  申请人：——

  公开号：US20150263297A1

  公开（公告）日：2015-09-17
• US9837622B2
  申请人：——

  公开号：US9837622B2

  公开（公告）日：2017-12-05
• [DE] METALLKOMPLEXE<br/>[EN] METAL COMPLEXES<br/>[FR] COMPLEXES METALLIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2014008982A1

  公开（公告）日：2014-01-16

  Die vorliegende Erfindung betrifft Metallkomplexe sowie elektronische Vorrichtungen, insbesondere organische Elektrolumineszenzvornchtungen, enthaltend diese Metallkomplexe.
• Conformational Isomers from Rotation of Diacetylenic Bond in an Ethynylpyrene-Substituted Molecular Hinge
  作者：Sethuraman Sankararaman、Gandikota Venkataramana、Babu Varghese

  DOI：10.1021/jo7024724

  日期：2008.3.1

  The first example of isolation and X-ray crystallographic structural characterization of two conformers arising from rotation along a diacetylenic bond is reported. In both the conformers extensive pi-pi interactions are observed in the solid state. VT-NMR and fluorescence spectroscopic studies in solution suggest that the closed and open conformers are in equilibrium and that the closed conformer is the predominant species at room temperature.