3,4,5-tris(nonyloxy)benzoic acid | 125836-62-6

• 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: 3,4,5-tris(nonyloxy)benzoic acid
• 英文别名: 3,4,5-Tri(nonoxy)benzoic acid
• CAS: 125836-62-6
• 化学式: C₃₄H₆₀O₅
• 分子量: 548.847
• InChiKey: FOJVOPJYVZSUOW-UHFFFAOYSA-N

物化性质

• 沸点：
  624.4±50.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  39
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(nonyloxy)benzoic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以6.915 g的产率得到3,4,5-tris(nonyloxy)benzyl alcohol
  参考文献：
  名称：

  Room Temperature Liquid Porphyrins

  摘要：

  报道了5,10,15,20-四(3,4,5-三烷氧基苯基)卟啉的合成，这些化合物在室温下表现出流态行为。热物性和流变学测量表明，它们在25°C（298 K）时表现得像液体。

  DOI：

  10.1246/cl.2010.714
• 作为产物：
  描述：

  1-溴壬烷 在 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,4,5-tris(nonyloxy)benzoic acid
  参考文献：
  名称：

  Room Temperature Liquid Porphyrins

  摘要：

  报道了5,10,15,20-四(3,4,5-三烷氧基苯基)卟啉的合成，这些化合物在室温下表现出流态行为。热物性和流变学测量表明，它们在25°C（298 K）时表现得像液体。

  DOI：

  10.1246/cl.2010.714

文献信息

• Exceptional dual fluorescent, excited-state intramolecular proton-transfer (ESIPT) columnar liquid crystals characterized by J-stacking and large Stokes shifts
  作者：Madhu Babu Kanakala、Channabasaveshwar V. Yelamaggad

  DOI：10.1016/j.molliq.2021.115879

  日期：2021.6

  microscopic, calorimetric and powder X-ray diffraction (XRD) studies evidence the occurrence of hexagonal columnar (Colh) phase having p6mm symmetry where the constituent slices result from the self-assembly of a pair of mesogens in a side-by-side manner facilitated by intense longitudinal π-π interactions. X-ray data confirm the absence of both directionally correlated tilting of the slices and transverse

  激发态分子内质子转移（ESIPT）荧光团正在成为电子和生物技术应用中有希望的未来材料。ESIPT柱状（Col）液晶（LC）已被特别预测为先进技术的合适材料。但是，几乎没有朝这个方向进行任何探索，因此需要立即予以注意。在这里，我们报告的合成，表征和ESIPT活性的同源系列的新型Phasmidic双（N- salicylideneaniline）Col LCs的合成。光学显微镜，量热法和粉末X射线衍射（XRD）研究表明，出现了p 6 mm的六方柱状（Col h）相对称性是指，由强烈的纵向π-π相互作用促进并列排列的一对液晶元的自组装产生了组成层。X射线数据证实了切片之间没有方向相关的倾斜和柱内的横向核-核相互作用。荧光探测清楚地证明了ESIPT不仅在介晶的DCM溶液中发生，而且还在其固态，液晶和各向同性液相的三个缩合状态下发生。通常，在ESIPT现象中观察到两个原型发射带，分别在〜430 nm（弱）和〜630
• Controlling the enthalpy–entropy competition in supramolecular fullerene liquid crystals by tuning the flexible chain length
  作者：Tiantian Zhu、Xiaoyan Zhang、Zhikai Li、Chih-Hao Hsu、Wei Chen、Toshikazu Miyoshi、Xiaohong Li、Xiaoming Yang、Yingfeng Tu、Christopher Y. Li

  DOI：10.1039/c7cc03195e

  日期：——

  We present here that in the two-dimensional (2D) crystal formed supramolecular fullerene liquid crystals (SLCs), the phase diagram and lamella thickness of SLCs and 2D crystals can be tuned by the flexible alkyl tail and spacer length, which has different effect on enthalpy and entropy changes during SLC formation.

  我们在这里介绍，在二维（2D）晶体形成的超分子富勒烯液晶（SLC）中，SLC和2D晶体的相图和薄片厚度可以通过柔性烷基尾和间隔基长度来调节，这对不同的影响SLC形成过程中焓和熵的变化。
• Crown ethers with lateral ortho-terphenyl units: effect of ester groups and sodium salts on the mesomorphic properties
  作者：Nelli Steinke、Michael Jahr、Matthias Lehmann、Angelika Baro、Wolfgang Frey、Stefan Tussetschläger、Sven Sauer、Sabine Laschat

  DOI：10.1039/b814536a

  日期：——

  Unsymmetrical crown ether derivatives 7 and 12 with one lateral o-terphenyl unit bearing different ester substituents were synthesized starting from methoxymethyl (MOM) protected bromobenzenes 3 and 8 by conversion into the respective borolanes 4 and 9, twofold Suzuki coupling with dibromobenzo[15]crown-5, acidic deprotection and finally esterification either with various alkanoic chlorides or gallic acids. Reaction with NaI provided the complexes [NaI·(7a–g)] and [NaI·(12a–d)], respectively. Uncomplexed crown ethers as well as their complexes [NaI·7a–c] and [NaI·12a–d] are non-mesogenic. In the case of [NaI·(7d–g)], however, the complexation induced a mesophase formation. As exemplarily shown for [NaI·7d], different textures were observed upon cooling, a fan-shaped texture, which is typical for a columnar hexagonal mesophase, and a striped fan-shaped texture, indicating a second mesophase Colx at low-temperature. From the SAXS diffraction pattern this mesophase was assigned to be columnar rectangular. For [NaI·7g] a different diffraction pattern was found, from which the low-temperature mesophase might be attributed to a soft crystal or a highly ordered columnar mesophase with orthorhombic symmetry.

  合成了不对称的冠醚衍生物7和12，这些衍生物具有一个侧链o-三苯基单元，并带有不同的酯取代基。合成起始于甲氧甲基（MOM）保护的溴苯3和8，通过转换成相应的硼烯烃4和9，进行双重铃木偶联反应，与二溴苯并[15]冠-5反应，随后进行酸性去保护，最后用各种烷基氯化物或鞣酸酯化。与NaI反应分别生成复合物[NaI·(7a–g)]和[NaI·(12a–d)]。未配位的冠醚以及它们的复合物[NaI·7a–c]和[NaI·12a–d]均不具备介晶性。然而，对于[NaI·(7d–g)]，复合作用引发了介相的形成。如[NaI·7d]所示，冷却时观察到不同的纹理，包括典型于柱状六角介相的扇形纹理，以及指示低温下第二种介相Colx的条纹扇形纹理。从小角X射线散射（SAXS）衍射图谱来看，该介相被归类为柱状矩形。对于[NaI·7g]，发现了不同的衍射图案，从中可以推测低温下的介相归因于软晶体或具有正交对称性的高度有序柱状介相。
• Tailoring thermotropic cubic mesophases: amphiphilic polyhydroxy derivatives
  作者：Konstanze Borisch、Siegmar Diele、Petra Göring、Horst Kresse、Carsten Tschierske

  DOI：10.1039/a705359b

  日期：——

  Novel amphiphilic polyhydroxy compounds [N-(3,4-dialkoxybenzoyl)-1-amino-1-deoxy-d-glucitols (glucamides), N-(3,4-dialkoxybenzoyl)-1-deoxy-1-methylamino-d-glucitols, N-(3,4,5-trialkoxybenzoyl)-1-deoxy-1-methylamino-d-glucitols (N-methylgucamides), 1-benzoylaminopropane-2,3-diols, 2-benzoylaminopropane-1,3-diols, 2-(3,4,5-tridodecyloxybenzoylamino)-2-(hydroxymethyl)propane-1,3-diol and (3,4,5-tridodecyloxybenzoyl)bis(2,3-dihydroxypropyl)amine] have been synthesized. Their thermotropic liquid crystalline phases were investigated by means of polarizing microscopy, differential scanning calorimetry and X-ray diffraction. Depending on the chain length, and the size of the hydrophilic polyhydroxy units, different mesophases have been found: smectic A phases (SA), inverted bicontinuous cubic phases (CubV2 , Ia3d), hexagonal columnar phases (ColH2) and micellar cubic mesophases (CubI2 , Pn3m or P43n). In strong analogy to lyotropic systems, the type of thermotropic mesophase depends on the ratio between the volume of the lipophilic moiety and the surface area of the hydrophilic moiety at the hydrophilic–lipophilic interface. The crossing from zero interface curvature (SA phase) to the finite negative curvature of the inverted cylindrical aggregates of the columnar mesophase takes place via bicontinuous cubic mesophases. The cylindrical aggregates of the columnar mesophase are stable over a rather broad range of variation of the structural parameter. At a certain degree of the size of the lipophilic moiety in respect to the surface area of the hydrophilic group, however, the transition from the hexagonal columnar to a micellar cubic mesophase takes place. On the basis of proton conductivity measurements and from packing considerations we propose that this cubic lattice is built up by eight closed micelles per unit cell which have a rod-like shape and represent small segments of extended columns. Therefrom we can propose a model for the transformations between these different thermotropic mesophases.

  新型两亲聚羟基化合物[N-(3,4-二烷氧基苯甲酰)-1-氨基-1-脱氧-d-葡萄糖醇（葡萄糖酰胺）、N-(3,4-二烷氧基苯甲酰)-1-脱氧-1-甲基氨基-d-葡萄糖醇、N-(3,4,5-三烷氧基苯甲酰)-1-脱氧-1-甲基氨基-d-葡萄糖醇（N-甲基葡萄糖酰胺）、1-苯甲酰氨基-丙烷-2,3-二醇、2-苯甲酰氨基-丙烷-1,3-二醇、2-(3,4,5-三十二烷氧基苯甲酰氨基)-2-(羟甲基)丙烷-1,3-二醇以及(3,4,5-三十二烷氧基苯甲酰)双(2,3-二羟基丙基)胺]已被合成。通过偏光显微镜、差示扫描量热法和X射线衍射法研究了它们的热致液晶相。根据链长和亲水性聚羟基单元的大小，发现了不同的介相：斜方相（SA）、倒置双连续立方相（CubV2，Ia3d）、六角柱相（ColH2）和胶束立方介相（CubI2，Pn3m或P43n）。与液晶系统非常相似，热致介相的类型取决于亲脂部分的体积与亲水部分在亲水-亲脂界面的表面积之间的比率。从零界面曲率（SA相）到柱状介相的有限负曲率倒置圆柱聚集体的过渡，通过双连续立方介相进行。柱状介相的圆柱聚集体在结构参数变化的较宽范围内是稳定的。然而，在亲脂部分与亲水基团表面积的某个比率下，发生从六角柱相到胶束立方介相的转变。根据质子导电性测量和包装考虑，我们提出该立方格子由每个单元格的八个闭合胶束构成，这些胶束呈杆状，代表扩展柱的小段。由此，我们可以提出一个不同热致介相之间转变的模型。
• Fastener effect on magnetic properties of chain compounds of dinuclear ruthenium carboxylates
  作者：Hideaki Ishida、Makoto Handa、Ichiro Hiromitsu、Masahiro Mikuriya

  DOI：10.2478/s11696-013-0366-0

  日期：2013.1.1

  Chlorido-bridged chain complexes of dinuclear ruthenium benzoate analogues, [Ru23,4,5-(CmH2m+1O)3C6H2CO2}4Cl]n (mCl) (m = 3, 5–7, 9, 11, 13, 15, 17), were synthesised and the crystal structure of 3Cl · 2nH2O was revealed. The magnetic measurements for a series of the complexes mCl (m = 2–18) revealed that all the complexes show an antiferromagnetic interaction between the dinuclear unit, with a fastener effect giving the stronger interaction as the alkyl-chain length m increases.

  摘要：合成了二核钌苯甲酸盐类似物的氯桥链配合物，[Ru23,4,5-(CmH2m+1O)3C6H2CO2}4Cl]n（mCl）（m = 3, 5–7, 9, 11, 13, 15, 17），并揭示了3Cl · 2nH2O的晶体结构。对一系列配合物mCl（m = 2–18）进行的磁性测量显示，所有配合物之间都表现出二核单位之间的反铁磁相互作用，随着烷基链长度m的增加，出现了更强的相互作用。