1-[4-[2-(4-Dodecanoylphenyl)ethynyl]phenyl]dodecan-1-one | 237761-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-[2-(4-Dodecanoylphenyl)ethynyl]phenyl]dodecan-1-one
• 英文别名: 1-[4-[2-(4-dodecanoylphenyl)ethynyl]phenyl]dodecan-1-one
• CAS: 237761-72-7
• 化学式: C₃₈H₅₄O₂
• 分子量: 542.846
• InChiKey: VKCKQMLYJBMOPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  40
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  1-[4-[2-(4-Dodecanoylphenyl)ethynyl]phenyl]dodecan-1-one 在 dicobalt octacarbonyl 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到1-[4-[2,3,4,5,6-Pentakis(4-dodecanoylphenyl)phenyl]phenyl]dodecan-1-one
  参考文献：
  名称：

  An Investigation of π−π Packing in a Columnar Hexabenzocoronene by Fast Magic-Angle Spinning and Double-Quantum ¹H Solid-State NMR Spectroscopy

  摘要：

  H-1 NMR methods employing very fast magic-angle spinning (MAS) are applied to the investigation of both the structure and dynamics of an alkyl-substituted hexa-peri-hexabenzocoronene (HBC), which is known to form a columnar mesophase with a very high one-dimensional charge carrier mobility. For the crystalline phase, three distinct aromatic resonances are identified in the single-quantum MAS spectrum. The observation of these distinct aromatic resonances is explained in terms of the differing degrees to which the aromatic protons experience the ring current of adjacent layers. Using the rotor-synchronized double-quantum MAS method, definite proton-proton proximities are identified, which are shown to be in agreement with the known crystal structure of unsubstituted HBC. In the liquid-crystalline phase, axial motion of the HBC disks leads to the averaging of the three sites into a single resonance. Furthermore, the reduction of the dipolar coupling caused by this motion is quantitatively investigated by an analysis of double-quantum MAS spinning sideband patterns. For all spectra, the resolution is significantly improved for a compound where the cw-carbon positions have been deuterated; the synthesis of this deuterated compound, in particular the final cyclodehydrogenation step, is described.

  DOI：

  10.1021/ja990637m
• 作为产物：
  描述：

  1-(4-溴苯基)十二烷-1-酮 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 四(三苯基膦)钯 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-[4-[2-(4-Dodecanoylphenyl)ethynyl]phenyl]dodecan-1-one
  参考文献：
  名称：

  An Investigation of π−π Packing in a Columnar Hexabenzocoronene by Fast Magic-Angle Spinning and Double-Quantum ¹H Solid-State NMR Spectroscopy

  摘要：

  H-1 NMR methods employing very fast magic-angle spinning (MAS) are applied to the investigation of both the structure and dynamics of an alkyl-substituted hexa-peri-hexabenzocoronene (HBC), which is known to form a columnar mesophase with a very high one-dimensional charge carrier mobility. For the crystalline phase, three distinct aromatic resonances are identified in the single-quantum MAS spectrum. The observation of these distinct aromatic resonances is explained in terms of the differing degrees to which the aromatic protons experience the ring current of adjacent layers. Using the rotor-synchronized double-quantum MAS method, definite proton-proton proximities are identified, which are shown to be in agreement with the known crystal structure of unsubstituted HBC. In the liquid-crystalline phase, axial motion of the HBC disks leads to the averaging of the three sites into a single resonance. Furthermore, the reduction of the dipolar coupling caused by this motion is quantitatively investigated by an analysis of double-quantum MAS spinning sideband patterns. For all spectra, the resolution is significantly improved for a compound where the cw-carbon positions have been deuterated; the synthesis of this deuterated compound, in particular the final cyclodehydrogenation step, is described.

  DOI：

  10.1021/ja990637m