3,3',4,4'-tetrabutoxy-biphenyl | 197313-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3',4,4'-tetrabutoxy-biphenyl
• 英文别名: 1,2-Dibutoxy-4-(3,4-dibutoxyphenyl)benzene
• CAS: 197313-05-6
• 化学式: C₂₈H₄₂O₄
• 分子量: 442.639
• InChiKey: DBXWIDHAZDDCPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3',4,4'-tetrabutoxy-biphenyl 在 盐酸 、 bi(cyclopentadienyl)platinum dichloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 150.0h， 生成 1,3-bis-[3-(3-methoxy-6,7,10,11-tetrabutoxy-triphenylen-2-yloxy)-propyl]-1,1,3,3-tetrahydroxy-disiloxane supramolecule
  参考文献：
  名称：

  通过使用pi堆积和H键结合的超结构进行顺式等规梯形聚倍半硅氧烷的受限合成。

  摘要：

  DOI：

  10.1002/anie.200504474
• 作为产物：
  描述：

  1,2-二丁氧基苯 在 铜 作用下， 以 氯仿 为溶剂， 生成 3,3',4,4'-tetrabutoxy-biphenyl
  参考文献：
  名称：

  The creation of long-lasting glassy columnar discotic liquid crystals using ‘dimeric’ discogens

  摘要：

  “二聚体”圆盘状分子已被合成，它们包含两个联苯并环己三烯核，每个核带有五个β-OC6H13取代基，通过剩余的β位点由柔性的O(CH2)nO聚甲撑链（n=3-16）连接。计算显示，这些化合物在Colh相中桥接列之间的最小链长为O(CH2)7O。研究发现，只有那些n>7的二聚体形成了Colh相。这种介相能过冷成相对坚硬且保持柱状有序和方向性的亚稳玻璃态。这些玻璃在几小时内会恢复到结晶态，但我们已证明，通过使“二聚体”微妙地不对称化，从而在玻璃中引入额外程度的无序，可以实现更持久Colh玻璃。这些“二聚体”在连接链的两端具有不同取代的联苯并环己三烯环，或在链本身内具有酰胺基团。它们生成的Colh有序玻璃在室温下可持续数月。

  DOI：

  10.1039/a810045d

文献信息

• 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。
• 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。
• Bushby; Lu, Synthesis, 2001, # 5, p. 763 - 767
  作者：Bushby、Lu

  DOI：——

  日期：——
• π-Conjugated Triphenylene Twins Exhibiting Polymesomorphism Including the Nematic Phase
  作者：Sanjay Kumar Varshney、Hideo Takezoe、Veena Prasad、D. S. Shankar Rao

  DOI：10.1080/15421400902987677

  日期：2009.12.7

  Novel discotic liquid crystals possessing two triphenylene (TP) mesogenic cores covalently connected via a rigid spacer, i.e., -conjugated ethynyl- or butadiynyl-bridge, (TP twins) are reported. The TP twins are categorized by the lengths of -substituted chains (R2 and R3) and peripheral alkoxy or branched aliphatic chains (R1 and R4). Three varieties of TP twins are prepared: A) TP twins having identical -substituted and peripheral chains (R1=R2=R3=R4), B) equivalent TP entities having a -substituted chain (R2=R3) and peripheral chains (R1=R4) of different length from the substitution, and C) TP twins with different TP entities having the same -substituted and peripheral alkoxy chains (R1=R2, R3=R4). The phase behavior is characterized by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (XRD) studies. These TP twins exhibit a discotic nematic (N) and/or columnar rectangular (Colr) mesophases over a wide temperature range. We found that the relative length of rigid spacer and -substituted alkoxy chains play an important role in the creation of the molecular self-assembly and formation of the mesophases. To the best of our knowledge, this is the first report of TP twins exhibiting polymesomorphism.