(2,4,6-Triethylbenzene)-1,3,5-triacetic acid | 220759-05-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2,4,6-Triethylbenzene)-1,3,5-triacetic acid
• 英文别名: 2,2',2''-(2,4,6-Triethylbenzene-1,3,5-triyl)triacetic acid；2-[3,5-bis(carboxymethyl)-2,4,6-triethylphenyl]acetic acid
• CAS: 220759-05-7
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: WEVUDBFKCZMZAX-UHFFFAOYSA-N

物化性质

• 沸点：
  518.1±45.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2,4,6-Triethylbenzene)-1,3,5-triacetic acid 在 N,N-二甲基甲酰胺 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Novel Artificial Receptors for Alkylammonium Ions with Remarkable Selectivity and Affinity

  摘要：

  The benzene-based tripodal tris(oxazolines) have been developed as the most selective and strong receptors toward linear alkylammonium ions reported to date. Among six tris(oxazolines) based on 2,4,6-trimethylbenzene framework, the phenylglycinol-derived receptor 4 exhibits the largest association constant toward nBuNH(3)(+) (logK(ass) = 6.65 +/- 0.02), while a similar value toward tBuNH(3)(+) (logK(ass) = 3.80 +/- 0.01) compared with others, which corresponds to the selectivity ratio of nBuNH(3)(+)/tBuNH(3)(+) as high as approximate to 700. The tris(oxazoline) 6 that has bare oxazoline ring exhibits still a large association hindered constant tBuNH(3)(+) toward sterically (logK(ass) = 5.26 +/- 0.02). Both receptors 4 and 6 extract beta-phenethylammonium ion from water into chloroform almost completely. When the benzene frame is changed from 2,4,6-trimethylbenzene to 2,4,6-triethylbenzene, dramatic changes in the affinity as well as in the selectivity are observed. The association constant observed by tris(oxazoline) 8 toward nBuNH(3)(+) approaches 10(8) M-1 and the selectivity ratio of nBuNH(3)(+)/tBuNH(3)(+) is increased to 2700. This selectivity is even more enhanced to 4000 with tris(oxazoline) 9. The enhanced binding affinity and high selectivity observed with receptors 4 and related derivatives 7-9 compared with others can be explained by an optimized steric and electronic environment provided by the phenyl substituents, which has been unambiguously demonstrated by X-ray crystallographic and H-1 NMR spectroscopic studies on the host-guest complexes. The new receptor system has several unique features such as ready availability, structural simplicity, and in particular versatility in derivatization. By virtue of these advantages, it can be readily tailored as selective receptors toward biologically important amines.

  DOI：

  10.1002/1521-3765(20000915)6:18<3399::aid-chem3399>3.0.co;2-m
• 作为产物：
  描述：

  1,3,5-三乙基苯 在 盐酸 、 氢溴酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2,4,6-Triethylbenzene)-1,3,5-triacetic acid
  参考文献：
  名称：

  “Flexiball”工具包：自组装胶囊的模块化方法

  摘要：

  我们报告了新的自组装分子胶囊的合成和表征。模块化策略利用与芳香族间隔元素相结合的多克量的甘脲结构单元。避免了早期胶囊遇到的冗长合成，现在可以使用几个纳米尺寸的胶囊。间隔物和甘脲模块之间的单键连接导致单体作为二聚体胶囊，其刚性低于早期对应物。使用 NMR 和 ESI 质谱的组合研究了同源和异源二聚体胶囊的主客体特性。它们对不同尺寸的客人表现出不太明显的选择性，并且当中央间隔单元上没有刚性元件时，它们增加的灵活性可以防止自组装。一些新胶囊带有向内定向的仲酰胺 NH 质子。这些可以进一步官能化，如它们的甲基化所示，得到叔类似物。这些结构对于在凹分子表面上放置官能团具有更广泛的意义。

  DOI：

  10.1021/ja011651d

文献信息

• Molecular Recognition of Carbohydrates with Acyclic Pyridine-Based Receptors
  作者：Monika Mazik、Wolfgang Radunz、Roland Boese

  DOI：10.1021/jo048979k

  日期：2004.10.1

  The recognition capabilities of acyclic pyridine-based receptors toward monosaccharides were evaluated. Aminopyridine receptors based on the 2,4,6-trimethyl- or 2,4,6-triethylbenzene frame show high β vs α binding selectivity in the recognition of glucopyranosides. Amidopyridine receptors, which are sterically less hindered at nitrogen, display high efficiency and an inverse selectivity. The 2-aminopyridine

  评估了基于无环吡啶的受体对单糖的识别能力。基于2,4,6-三甲基或2,4,6-三乙苯骨架的氨基吡啶受体在识别吡喃葡萄糖苷方面表现出高的β对α结合选择性。在氮上空间受阻较少的氨基吡啶受体显示出高效率和相反的选择性。已经建立了2-氨基吡啶基团作为单糖结合中的高效识别基团。影响受体的结合性能的因素1 - 15，这在本质上和用作建筑块结合和间隔物亚单位数目不同，进行了讨论。
• Synthesis and Binding Studies of Bowl-Shaped Hosts for Quaternary Ammoniums
  作者：Kyu-Sung Jeong、Kwang Hoon Shin、Soong-Hyun Kim

  DOI：10.1246/cl.2002.1166

  日期：2002.12

  Two bowl-shaped hosts for quaternary ammonium salts were synthesized and their binding properties, along with the anion effect, were systematically examined and compared in CDCl3.

  合成了两种碗状主客体用于季铵盐，并系统地检查和比较了它们的结合特性及阴离子效应，实验在CDCl3中进行。
• Tripodal oxazoline-based homochiral coordination cages with internal binding sites
  作者：Jeongryul Kim、Dowook Ryu、Yoshihisa Sei、Kentaro Yamaguchi、Kyo Han Ahn

  DOI：10.1039/b514697f

  日期：——

  Homochiral coordination cages, which have two well-defined internal binding sites for ammonium and organoammonium ions, have been constructed by Pd(II)-mediated self-assembly of preorganized tripodal oxazolines containing pyridine pendant groups.

  同手性配位笼通过Pd(II)介导的自组装构建而成，这些配位笼具有两个明确定义的内部结合位点，用于铵离子和有机铵离子，所用的原料是含有吡啶侧链的预组装三支氧佐啉。
• A synthetic receptor for hydrogen-bonding to fluorines of trifluoroborates
  作者：Per Restorp、Orion B. Berryman、Aaron C. Sather、Dariush Ajami、Julius Rebek Jr.

  DOI：10.1039/b914171e

  日期：——

  A tripodal receptor featuring three inwardly-directed hydrogen-bond donors binds covalently bound fluorine atoms of trifluoroborates through hydrogen-bonding.

  一种三足受体，具有三个向内的氢键供体，通过氢键与三氟硼酸盐中的共价结合氟原子结合。
• Chiral Discrimination of α-Chiral Ammonium Ions by Sterically Geared Chiral Tripodal Oxazolines
  作者：Sung-Gon Kim、Sunderraman Sambasivan、Kyo-Han Ahn

  DOI：10.5012/bkcs.2010.31.03.724

  日期：2010.3.20

  ” conformation (“1,3,5-up/2,4,6-down” conformation) to avoid otherwise increased steric repulsion between the vicinal substituents of the benzene frame. Use of such sterically bulky subunits within a molecule to enable it to adopt a thermodynamically favored conformation with mini-mum steric interactions has been dubbed as “steric gearing.”

  ”构象（“1,3,5-up/2,4,6-down”构象）以避免苯框架的邻位取代基之间的空间排斥增加。在分子中使用这种空间庞大的亚基，使其能够采用具有最小空间相互作用的热力学有利构象，被称为“空间传动”。