2,3,7,8,12,13-hexapentoxytricycloquinazoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3,7,8,12,13-hexapentoxytricycloquinazoline
• 英文别名: 4,5,12,13,20,21-Hexapentoxy-8,16,24,25-tetrazahexacyclo[15.7.1.02,7.09,25.010,15.018,23]pentacosa-1(24),2,4,6,8,10,12,14,16,18,20,22-dodecaene
• 化学式: C₅₁H₇₂N₄O₆
• 分子量: 837.156
• InChiKey: CIHVUTKAYUOLJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  61
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  95.7
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-溴戊烷 、 2,3,7,8,12,13-Tricycloquinazolinehexol (9CI) 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以35%的产率得到2,3,7,8,12,13-hexapentoxytricycloquinazoline
  参考文献：
  名称：

  Hexaalkoxytricycloquinazolines: new discotic liquid crystals

  摘要：

  Tricycloquinazoline (TCQ), a molecule of both biological and physical interest, has been found to function as the core fragment for a new family of discotic mesogens, which have C3 symmetry and six aliphatic side chains. Six representative homologous 2,3,7,8,12,13-hexaalkoxy-TCQ derivatives 5 were synthesized, with alkyl side chain lengths varying from 3 to 16 carbon atoms. These highly fluorescent, heteroaromatic compounds are conveniently obtained by alkylation of hexahydroxy-TCQ, 10. The latter is prepared by trimerization of 5,6-dimethoxyanthranil, 8, followed by demethylation of the resultant hexamethoxy-TCQ, 9. All compounds, 5, are mesogenic within a very broad temperature range. The nature of these new mesophases was studied by DSC and by optical microscopy with polarized light and X-ray diffraction. DSC measurements show highly reversible behavior at both melting and clearing points, indicating high chemical stability. Photomicroscopic pictures show mosaic textures, characteristic of an ordered hexagonal, columnar phase (D(ho)), that are very similar to those we reported earlier for hexakis(thioalkoxy)-TCQ derivatives 4. The diffraction spacings of two representative compounds (having 5 and 11 carbon atoms in the side chain) in the mesophase are consistent with a two-dimensional hexagonal lattice having unit cell sides of a = 21.2 and 28.7 angstrom, respectively, and containing one molecule per unit cell.

  DOI：

  10.1021/jo00067a013

文献信息

• Hexaalkoxytricycloquinazolines: new discotic liquid crystals
  作者：Sandeep Kumar、Ellen J. Wachtel、Ehud Keinan

  DOI：10.1021/jo00067a013

  日期：1993.7

  Tricycloquinazoline (TCQ), a molecule of both biological and physical interest, has been found to function as the core fragment for a new family of discotic mesogens, which have C3 symmetry and six aliphatic side chains. Six representative homologous 2,3,7,8,12,13-hexaalkoxy-TCQ derivatives 5 were synthesized, with alkyl side chain lengths varying from 3 to 16 carbon atoms. These highly fluorescent, heteroaromatic compounds are conveniently obtained by alkylation of hexahydroxy-TCQ, 10. The latter is prepared by trimerization of 5,6-dimethoxyanthranil, 8, followed by demethylation of the resultant hexamethoxy-TCQ, 9. All compounds, 5, are mesogenic within a very broad temperature range. The nature of these new mesophases was studied by DSC and by optical microscopy with polarized light and X-ray diffraction. DSC measurements show highly reversible behavior at both melting and clearing points, indicating high chemical stability. Photomicroscopic pictures show mosaic textures, characteristic of an ordered hexagonal, columnar phase (D(ho)), that are very similar to those we reported earlier for hexakis(thioalkoxy)-TCQ derivatives 4. The diffraction spacings of two representative compounds (having 5 and 11 carbon atoms in the side chain) in the mesophase are consistent with a two-dimensional hexagonal lattice having unit cell sides of a = 21.2 and 28.7 angstrom, respectively, and containing one molecule per unit cell.