2,3,6,7,10,11-hexabutoxytriphenylene | 70351-85-8

• 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: 2,3,6,7,10,11-hexabutoxytriphenylene
• 英文别名: 2,3,6,7,10,11-hexabutyloxytriphenylene
• CAS: 70351-85-8
• 化学式: C₄₂H₆₀O₆
• 分子量: 660.935
• InChiKey: KNEJSELDOYMNMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  48
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,6,7,10,11-hexabutoxytriphenylene 在 四(三苯基膦)钯 溴 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 2,3,6,7,10,11-hexabutoxy-1,4,8-tris(3,4-dichlorophenyl)triphenylene
  参考文献：
  名称：

  Facile Synthesis of Janus “Double-Concave” Tribenzo[a,g,m]coronenes

  摘要：

  [GRAPHICS]Hexabutoxytribenzo[a,g,m]coronenes have been prepared in three steps from readily accessible hexabutoxytriphenylene. Single-crystal X-ray diffraction analysis reveals that these molecules can adopt an extraordinary "double-concave" conformation that makes them ideal hosts for the binding of different guest molecules at each face.

  DOI：

  10.1021/jo0701029
• 作为产物：
  描述：

  1,2-二丁氧基苯 在 五氯化钼 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以95%的产率得到2,3,6,7,10,11-hexabutoxytriphenylene
  参考文献：
  名称：

  Oxidative trimerization of o-dialkoxybenzenes to hexaalkoxytriphenylenes: molybdenum(v) chloride as a novel reagent

  摘要：

  对称取代的六烷氧基三苯ylene可通过与MoCl₅的氧化三聚反应，以高产率从o-二烷氧基苯获得；3,3′,4,4′-四烷氧基联苯与1,2-二烷氧基苯的氧化偶联反应生成不对称取代的三苯ylene衍生物，而3,3′,4,4′-四烷氧基联苯与烷氧基酚的直接偶联，则产生单功能化的三苯ylene。

  DOI：

  10.1039/a704130f

文献信息

• Synthesis and mesomorphism of triphenylene-based dimers with a highly ordered columnar plastic phase
  作者：Yifei Wang、Chunxiu Zhang、Hao Wu、Jialing Pu

  DOI：10.1039/c3tc31986e

  日期：——

  were confirmed by proton nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, high-resolution mass spectrometry and elemental analysis. The mesomorphic properties of these compounds were investigated by differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction. It was found that these dimers for which n > 4 formed a highly ordered columnar plastic

  一系列基于苯并菲盘状二聚体已被合成，每个三亚苯核的带有5β-OC 4个H ^ 9取代基，其通过柔性o通过剩余的β位连接（CH 2）Ñ ø聚亚甲基链（Ñ = 2–12）。通过质子核磁共振光谱，傅立叶变换红外光谱，高分辨率质谱和元素分析证实了它们的化学结构。通过差示扫描量热法，偏振光学显微镜和X射线衍射研究了这些化合物的介晶性质。结果发现，这些二聚体为此ñ> 4形成高度有序的柱状塑性相，其中一些（n = 6、7、10、11和12）表现出多个中间相。这是我们首次将矩形柱状塑性相定义为化合物4d（n = 5）的新型液晶相。在相邻分子之间引入单个互连链不会显着干扰柱状塑性相的形成，但会丰富盘状分子的中间相并阻碍结晶。可以将4e–k（n = 6–12）的中间相过冷至玻璃状态，其中保留了自组装柱状结构。
• Synthesis and specific features of mesomorphic behavior of new polysubstituted triphenylenes
  作者：O. V. Zemtsova、K. N. Zheleznov

  DOI：10.1007/s11172-005-0028-7

  日期：2004.8

  Previously unknown 2,3,6,7,10,11-hexakis(dodecyloxy)triphenylene and -(tetradecyloxy)triphenylene were synthesized. The structures of the synthesized compounds were proved by elemental analysis and spectral methods. Polymesomorphism was found for the first time and studied for substances of the hexaalkoxytriphenylene homologic series, as well as liotropic mesomorphism in a series of organic solvents

  合成了以前未知的 2,3,6,7,10,11-hexakis(dodecyloxy)triphenylene 和 -(tetradecyloxy)triphenylene。通过元素分析和光谱方法证实了合成化合物的结构。首次发现并研究了六烷氧基三亚苯基同系物质的多介晶现象，以及一系列有机溶剂中的异致介晶现象。
• Oxidative trimerization of o-dialkoxybenzenes to hexaalkoxytriphenylenes: molybdenum(v) chloride as a novel reagent
  作者：Sandeep Kumar、M. Manickam

  DOI：10.1039/a704130f

  日期：——

  Symmetrically substituted hexaalkoxytriphenylenes are obtained from o-dialkoxybenzenes by oxidative trimerization with MoCl 5 in high yields; oxidative coupling of a 3,3′,4,4′-tetraalkoxybiphenyl and 1,2-dialkoxybenzenes yields unsymmetrically substituted derivatives of triphenylene and a direct coupling of a 3,3′,4,4′-tetraalkoxybiphenyl with alkoxyphenol produces the monofunctionalized triphenylenes.

  对称取代的六烷氧基三苯ylene可通过与MoCl₅的氧化三聚反应，以高产率从o-二烷氧基苯获得；3,3′,4,4′-四烷氧基联苯与1,2-二烷氧基苯的氧化偶联反应生成不对称取代的三苯ylene衍生物，而3,3′,4,4′-四烷氧基联苯与烷氧基酚的直接偶联，则产生单功能化的三苯ylene。
• Triazacoronene Derivatives with Three <i>peri</i> -Benzopyrano Extensions: Synthesis, Structure, and Properties
  作者：Bo Liu、Donghui Shi、Yihui Yang、Dayong Liu、Ming Li、Ernu Liu、Xiaogang Wang、Qiang Zhang、Mingyu Yang、Jing Li、Xianying Shi、Wenliang Wang、Junfa Wei

  DOI：10.1002/ejoc.201701386

  日期：2018.2.21

  New π-extended triazacoronene derivatives containing three peri-benzopyrano extensions were successfully synthesized through tandem triflic acid catalyzed threefold Pictet–Spengler cyclization and K2CO3-catalyzed ipso-aromatic substitution in one pot. The structure was verified by X-ray diffraction analysis and was found to form a sandwich-type π trimer in the crystalline state. The π-extended triazacoronenes

  通过串联三氟甲磺酸催化的三重 Pictet-Spengler 环化和 K2CO3 催化的同位芳族取代在一锅中成功合成了含有三个 peri-benzopyrano 延伸的新型 π 延伸的三氮杂可酮衍生物。通过X射线衍射分析证实了该结构，并发现在结晶状态下形成夹心型π三聚体。π 扩展的三氮杂可酮表现出合理的溶解度、高热稳定性和显着可重复的电致发光发射。
• 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。