1-amino-2,3,6,7,10,11-hexaheptyloxytriphenylene | 221147-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-amino-2,3,6,7,10,11-hexaheptyloxytriphenylene
• 英文别名: 2,3,6,7,10,11-Hexakis(heptyloxy)triphenylen-1-amine；2,3,6,7,10,11-hexaheptoxytriphenylen-1-amine
• CAS: 221147-26-8
• 化学式: C₆₀H₉₇NO₆
• 分子量: 928.433
• InChiKey: FQTFEKDEGAPPDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.3
• 重原子数：
  67
• 可旋转键数：
  42
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  R-(+)-硫辛酸 、 1-amino-2,3,6,7,10,11-hexaheptyloxytriphenylene 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (R)-5-(1,2-dithiolan-3-yl)-N-[2,3,6,7,10,11-hexakis(heptyloxy)triphenylen-1-yl]pentanamide
  参考文献：
  名称：

  Effect of the nature of chiral fragment on mesomorphic properties of triphenylene ethers

  摘要：

  A number of new 2,3,6,7,10,11-hexakis(heptyloxy)triphenylenes possessing a chiral substituent in position 1 of the triphenylene ring system and characterized by predictable mesomorphism were synthesized. The effect of the nature of the chiral fragment (dehydrocholic, lipoic, and d-tartaric acid residues) on the mesomorphic properties of triphenlylene ethers was studied. N-[2,3,6,7,10,11-hexakis(heptylozy)triphenylen-1-yl]amides derived from the above acids, unlike initial monomesomorphic amine, exhibit enantiotropic columnar polymorphism and give rise to helical columnar structure at reduced temperature. The newly synthesized amides are characterized by lower thermal stability and broader temperature range of the mesophase. Introduction of two chiral dehydrocholic acid fragments into the triphenylene core favors columnar (including chiral) mesomorphism.

  DOI：

  10.1134/s1070363211040165
• 作为产物：
  描述：

  hexaheptyloxytriphenylene 在 tin 、 硝酸 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.33h， 生成 1-amino-2,3,6,7,10,11-hexaheptyloxytriphenylene
  参考文献：
  名称：

  Effect of the nature of chiral fragment on mesomorphic properties of triphenylene ethers

  摘要：

  A number of new 2,3,6,7,10,11-hexakis(heptyloxy)triphenylenes possessing a chiral substituent in position 1 of the triphenylene ring system and characterized by predictable mesomorphism were synthesized. The effect of the nature of the chiral fragment (dehydrocholic, lipoic, and d-tartaric acid residues) on the mesomorphic properties of triphenlylene ethers was studied. N-[2,3,6,7,10,11-hexakis(heptylozy)triphenylen-1-yl]amides derived from the above acids, unlike initial monomesomorphic amine, exhibit enantiotropic columnar polymorphism and give rise to helical columnar structure at reduced temperature. The newly synthesized amides are characterized by lower thermal stability and broader temperature range of the mesophase. Introduction of two chiral dehydrocholic acid fragments into the triphenylene core favors columnar (including chiral) mesomorphism.

  DOI：

  10.1134/s1070363211040165

文献信息

• Construction, synthesis and study of new discotic mesogens
  作者：O. B. Akopova

  DOI：10.1007/s10947-006-0276-x

  日期：2006.1

  The calculation and analysis of molecular parameters (MPs) has been carried out for five series of triphenylene derivatives and crown ether derivatives (30 molecules) containing chiral or complexing centers. The values of the MP were used to predict possible occurrence of columnar and nematic mesomorphism in these series. Several representatives of these series were synthesized and their mesomorphic behavior was studied. A special attention was paid to enamine ketone derivatives of crown ether, in which the transition from the liquid-crystal state to the vitreous state with retention of the mesophase structure at the ambient temperature was observed.

  对含有手性或络合中心的五系列三苯衍生物和冠醚衍生物（30个分子）进行了分子参数（MP）的计算和分析。利用MP值预测这些系列中可能出现的柱状和线状介晶现象。合成了这些系列中的几个代表，并研究了它们的介晶行为。特别关注了冠醚的烯胺酮衍生物，观察到其在环境温度下从液晶态转变为玻璃态并保留介晶结构。
• ——
  作者：O. V. Zemtsova、O. K. Syromyatnikova、L. N. Kotovich、O. B. Akopova

  DOI：10.1023/a:1010411804065

  日期：——

  This paper reports on synthesis and investigation of columnar mesophases of the new members of the homologous series of nitro and amino derivatives of hexaalkoxytriphenylenes, whose mesomorphism was predicted earlier. The forecast is in good agreement with the experimental data. The effect of the introduction of the donor and acceptor groups into the central fragment of triphenylene on the phase transition temperature, texture, and range of existence of columnar mesophases is examined. The predicting ability of the molecular parameters suggested previously for the series under analysis is discussed. It is found that introduction of a nitro group, which is a strong electron acceptor, into the central fragment of triphenylene lowers the melting temperature of the compound versus its analog and does not promote columnar mesomorphism in the lower nonmesomorphous homologs. At the same time, this slightly expands the range of existence of the mesophase in higher homologs.
• Synthesis and study of heptasubstituted triphenylenes with chiral fragments and predictable type of mesomorphism
  作者：O. B. Akopova、E. V. Kurbatova、M. S. Gruzdev

  DOI：10.1134/s1070363210020155

  日期：2010.2

  The forecasting of columnar and chiral mesomorphism was done for the new series of triphenylene derivatives. The mesomorphic properties of the two heptasubstituted triphenylenes containing chiral fragments were studied. The prediction results agreed well with the experimental data. Anilides of 1-amino-2,3,6,7,10,11-hexa(heptyloxy)triphenylene with abietic and dihydrocholic acids were found to exhibit the enantiotropic columnar dimesomorphism and to display the chiral columnar mesophases in the low-temperature range. The anilides obtained possess a lower thermal stability and extended interval of the mesophase existence than the initial amine.
• Polysubstituted triphenylenes with active groups. Molecular parameters, synthesis, structure, and mesomorphism
  作者：O. B. Akopova、A. A. Bronnikova、A. Kruvchinskii、L. N. Kotovich、L. S. Shabyshev、L. A. Valkova

  DOI：10.1007/bf02873645

  日期：1998.11

  Molecular parameters of hexaalkoxybiphenylenes with different substituents on the periphery of the triphenylene nucleus of known and hypothetical structures are calculated, The probability of a discophase for compounds of this series is estimated from molecular parameters. Several compounds of this series having polar groups (NO2, NH2) in the I position of the triphenylene nucleus have been synthesized The compounds synthesized were investigated by thermopolarizing microscopy and X-ray diffraction analysis. The data on the mesomorphism of the new compounds are in good agreement with our prediction that alkoxytriphenylenes with polar groups have a discophase. It is established that introduction of an electron-accepting group at position I of the triphenylene nucleus expands the temperature range of existence of the discophase to room temperature. On the contrary, introduction of an electron-donating group narrows this interval. Compounds of this series presumably have a hexagonal columnar structure.
• Synthesis and investigation of triphenylene discotic derivatives with donor and acceptor groups and with predictable type of mesomorphism
  作者：O. B. Akopova、E. V. Kurbatova、M. S. Gruzdev

  DOI：10.1134/s1070363208100149

  日期：2008.10

  Prognosis of columnar mesomorphism is performed, five new hexa- and hepta-substituted triphenylene derivatives with donor and acceptor groups are synthesized and their mesomorphoc properties are stusied. Good agreement is achieved between predictions and experiments. The synthesized triphenylene derivatives are found to display enantiotropic columnar mesomorphism. 1-Amino-2,3,6,7,10,11-hexaheptyloxytriphenylene anilides of 2,3,5-triiodo-, 3,4,5-trihydroxy- and 4-nitro-benzoic acids reveal enantiotropic dimesomorphism. Also found decrease in thermal stability and extension of the interval of existence of mesophase at introduction to triphenylene frame of substituents with acceptor groups at the amino group.