diethyl 6-(1-hexadecynyl)-2-methoxyazulene-1,3-dicarboxylate | 1285535-36-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: diethyl 6-(1-hexadecynyl)-2-methoxyazulene-1,3-dicarboxylate
• CAS: 1285535-36-5
• 化学式: C₃₃H₄₆O₅
• 分子量: 522.725
• InChiKey: TVDOGVZKGWIXLA-UHFFFAOYSA-N

物化性质

• 熔点：
  57.2-57.7 °C(Solvent: Methanol)
• 沸点：
  633.2±50.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  38.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 6-(1-hexadecynyl)-2-methoxyazulene-1,3-dicarboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 以94%的产率得到diethyl 6-hexadecyl-2-methoxyazulene-1,3-dicarboxylate
  参考文献：
  名称：

  Synthesis and liquid crystalline behavior of azulene-based liquid crystals with 6-hexadecyl substituents on each azulene ring

  摘要：

  Hexakis(6-hexadecyl-2-azulenyl)benzene (1b) has been synthesized by Co-2(CO)8-catalyzed cyclotrimerization reaction of bis(6-hexadecyl-2-azulenyl)acetylene (2b). The mesomorphic behaviors of 1b, 2b, and 6-hexadecyl-2-phenylazulene (3b) were studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction (XRD) techniques and their mesomorphic properties were compared with those of their 6-octyl derivatives 1a, 2a, and 3a. Increase of the number of carbon atoms in the peripheral side chains drops the isotropization temperatures of 1b, 2b, and 3b by 56.9 degrees C, 33 degrees C, and 23.6 degrees C, respectively. Additionally, the phase-transition behavior varied with increase of the number of the peripheral chains, as well as decrease of the crystalline-mesophase transition temperatures, except for compound 3b. As the results, spontaneous monodomain homeotropic molecular alignment was revealed by compound 1b in its Col(hd) mesophase on non-treated glass substrate, which would be attracted to the application for the device fabrication of molecular materials. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.08.012
• 作为产物：
  描述：

  1-十六炔 、 diethyl 6-bromo-2-methoxyazulene-1,3-dicarboxylate 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以99%的产率得到diethyl 6-(1-hexadecynyl)-2-methoxyazulene-1,3-dicarboxylate
  参考文献：
  名称：

  Synthesis and liquid crystalline behavior of azulene-based liquid crystals with 6-hexadecyl substituents on each azulene ring

  摘要：

  Hexakis(6-hexadecyl-2-azulenyl)benzene (1b) has been synthesized by Co-2(CO)8-catalyzed cyclotrimerization reaction of bis(6-hexadecyl-2-azulenyl)acetylene (2b). The mesomorphic behaviors of 1b, 2b, and 6-hexadecyl-2-phenylazulene (3b) were studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction (XRD) techniques and their mesomorphic properties were compared with those of their 6-octyl derivatives 1a, 2a, and 3a. Increase of the number of carbon atoms in the peripheral side chains drops the isotropization temperatures of 1b, 2b, and 3b by 56.9 degrees C, 33 degrees C, and 23.6 degrees C, respectively. Additionally, the phase-transition behavior varied with increase of the number of the peripheral chains, as well as decrease of the crystalline-mesophase transition temperatures, except for compound 3b. As the results, spontaneous monodomain homeotropic molecular alignment was revealed by compound 1b in its Col(hd) mesophase on non-treated glass substrate, which would be attracted to the application for the device fabrication of molecular materials. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.08.012