1,2,3-tris(pentyloxy)benzene | 119891-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2,3-tris(pentyloxy)benzene
• 英文别名: 1,2,3-tri(pentyloxy)benzene；1,2,3-Tripentoxybenzene
• CAS: 119891-28-0
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: GHUYWIWBPUMKCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3-tris(pentyloxy)benzene 在 硝酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到3,4,5-tri(pentyloxy)nitrobenzene
  参考文献：
  名称：

  A New Class of Discotic Mesogens Derived from Tris(N-salicylideneaniline)s Existing in C_3h and C_s Keto-Enamine Forms

  摘要：

  Two series of a unique class of columnar liquid crystals derived from tris(N-salicylideneaniline)s [TSANs] in which the proton and the electron interact with each other through the H-bonding environment are reported. The synthesis is carried out by condensing 1,3,5-triformylphloroglucinol with the respective dialkoxyanilines or trialkoxyanilines. H-1 NMR and H-1-H-1 COSY NMR studies revealed their existence as an inseparable mixture of two keto-enamine tautomeric forms with C-3h and C-s rotational symmetries instead of the expected enol-imine form. The influence of the number of peripheral alkoxy tails on the columnar mesomorphic behavior is investigated by using polarizing optical microscopy, differential scanning calorimetry, and X-ray scattering. The fluid/glassy columnar states probed for a number of representative compounds confirmed the D-6h (hexagonal) or D-2h (rectangular) symmetry of the columns. The electronic absorption and emission characteristics of these compounds have been studied in both mesomorphic and solution states. Of special interest, the photoluminescence spectra of solution and fluid/ glassy two-dimensional structure evidently disclose the promising light generating capability of these new discotics systems.

  DOI：

  10.1021/jo0712650
• 作为产物：
  描述：

  1-溴戊烷 、 邻苯三酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以73%的产率得到1,2,3-tris(pentyloxy)benzene
  参考文献：
  名称：

  A New Class of Discotic Mesogens Derived from Tris(N-salicylideneaniline)s Existing in C_3h and C_s Keto-Enamine Forms

  摘要：

  Two series of a unique class of columnar liquid crystals derived from tris(N-salicylideneaniline)s [TSANs] in which the proton and the electron interact with each other through the H-bonding environment are reported. The synthesis is carried out by condensing 1,3,5-triformylphloroglucinol with the respective dialkoxyanilines or trialkoxyanilines. H-1 NMR and H-1-H-1 COSY NMR studies revealed their existence as an inseparable mixture of two keto-enamine tautomeric forms with C-3h and C-s rotational symmetries instead of the expected enol-imine form. The influence of the number of peripheral alkoxy tails on the columnar mesomorphic behavior is investigated by using polarizing optical microscopy, differential scanning calorimetry, and X-ray scattering. The fluid/glassy columnar states probed for a number of representative compounds confirmed the D-6h (hexagonal) or D-2h (rectangular) symmetry of the columns. The electronic absorption and emission characteristics of these compounds have been studied in both mesomorphic and solution states. Of special interest, the photoluminescence spectra of solution and fluid/ glassy two-dimensional structure evidently disclose the promising light generating capability of these new discotics systems.

  DOI：

  10.1021/jo0712650

文献信息

• Synthesis of Triphenylene and Dibenzopyrene Derivatives: Vanadium Oxytrichloride a Novel Reagent
  作者：Sandeep Kumar、Sanjay K. Varshney

  DOI：10.1055/s-2001-10821

  日期：——

  This paper presents an efficient synthetic procedure for the preparation of various triphenylene and dibenzopyrene derivatives using VOCl3 as a novel reagent. Symmetrically substituted hexaalkoxytriphenylenes are obtained from o-dialkoxybenzenes by oxidative trimerization with VOCl3 in high yields. The oxidative coupling of a 3,3′,4,4′-tetraalkoxybiphenyl and 1,2-dialkoxybenzenes or 1,2,3-trialkoxybenzenes affords unsymmetrically substituted derivatives of triphenylene. The reagent oxidizes 3,3′,4,4′-tetraalkoxybiphenyl efficiently to 2,5,6,9,12,13-hexaalkoxydibenzo[fg,op]naphthacene-1,8-quinone and its 1,10-quinone isomer. Both the quinones can be converted to liquid crystalline derivatives using well-established chemistry. Effects of solvent, reagent concentration, acid catalyst and temperature have been studied.

  本文介绍了一种使用 VOCl3 作为新型试剂制备各种三亚苯和二苯并芘衍生物的高效合成方法。用 VOCl3 氧化三聚法从邻二烷氧基苯得到了对称取代的六烷氧基三亚苯，产率很高。将 3,3′,4,4′-四烷氧基联苯与 1,2-二烷氧基苯或 1,2,3-三烷氧基苯氧化偶联，可得到不对称取代的三亚苯衍生物。该试剂可将 3,3′,4,4′-四烷氧基联苯高效氧化为 2,5,6,9,12,13-六烷氧基二苯并[fg,op]萘-1,8-醌及其 1,10-醌 异构体。这两种醌类化合物都可以利用成熟的化学方法转化为液晶衍生物。研究了溶剂、试剂浓度、酸催化剂和温度的影响。
• Novel heptasubstituted triphenylene discotic liquid crystals
  作者：Sandeep Kumar、M. Manickam、Sanjay K. Varshney、D. S. Shankar Rao、S. Krishna Prasad

  DOI：10.1039/b005773h

  日期：——

  The synthesis and characterisation of several hepta-substituted triphenylene derivatives are reported. These unsymmetrically substituted triphenylene derivatives are of three varieties, i) with seven identical peripheral alkoxy chains, ii) two or three out of the seven alkoxy chains have different chain lengths and, iii) the mode of the attachment of two of the peripheral chains is different, i.e.via ester linkages. The heptaalkoxytriphenylenes were prepared by two different routes, either starting from monohydroxypentakis(alkoxy)triphenylenes or via a biphenyl route using either MoCl5 or FeCl3 as oxidants. Unsymmetrical substitution has a large effect on the thermal behaviour but the type of mesophase formed does not change. Photomicroscopic pictures of all the 21 liquid crystalline compounds reported here show classical textures of an ordered hexagonal columnar (Colh) phase. X-Ray diffraction studies of five representative compounds confirmed the above conclusions. Mixed ether–ester derivatives have smaller core–core separations and higher correlation length, therefore, are better candidates for charge transport studies.

  报告了几种庚代三亚苯衍生物的合成和特性。这些不对称取代的三亚苯基衍生物有三种类型：①具有七条相同的外围烷氧基链；②七条烷氧基链中的两条或三条具有不同的链长；③两条外围链的连接方式不同，即通过酯连接。七烷氧基三亚苯的制备有两种不同的路线，一种是从单羟基五（烷氧基）三亚苯开始，另一种是以 MoCl5 或 FeCl3 作为氧化剂，通过联苯路线制备。不对称取代对热性能有很大影响，但形成的介相类型并没有改变。本文报告的所有 21 种液晶化合物的光电显微图片都显示了有序六方柱状（Colh）相的经典纹理。对五种代表性化合物进行的 X 射线衍射研究证实了上述结论。 混合醚酯衍生物的核心-核心分离度较小，相关长度较高，因此更适于电荷传输研究。
• A New Class of Discotic Mesogens Derived from Tris(<i>N</i>-salicylideneaniline)s Existing in <i>C</i>₃<i>_h</i> and <i>C</i><i>_s</i> Keto-Enamine Forms
  作者：Channabasaveshwar V. Yelamaggad、Ammathnadu S. Achalkumar、D. S. Shankar Rao、S. Krishna Prasad

  DOI：10.1021/jo0712650

  日期：2007.10.1

  Two series of a unique class of columnar liquid crystals derived from tris(N-salicylideneaniline)s [TSANs] in which the proton and the electron interact with each other through the H-bonding environment are reported. The synthesis is carried out by condensing 1,3,5-triformylphloroglucinol with the respective dialkoxyanilines or trialkoxyanilines. H-1 NMR and H-1-H-1 COSY NMR studies revealed their existence as an inseparable mixture of two keto-enamine tautomeric forms with C-3h and C-s rotational symmetries instead of the expected enol-imine form. The influence of the number of peripheral alkoxy tails on the columnar mesomorphic behavior is investigated by using polarizing optical microscopy, differential scanning calorimetry, and X-ray scattering. The fluid/glassy columnar states probed for a number of representative compounds confirmed the D-6h (hexagonal) or D-2h (rectangular) symmetry of the columns. The electronic absorption and emission characteristics of these compounds have been studied in both mesomorphic and solution states. Of special interest, the photoluminescence spectra of solution and fluid/ glassy two-dimensional structure evidently disclose the promising light generating capability of these new discotics systems.