2,4,6-三甲基-1,3,5-苯三乙酸 | 40207-09-8

• 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
• 中文名称: 2,4,6-三甲基-1,3,5-苯三乙酸
• 中文别名: (3,5-双羧基甲基-2,4,6-三甲基苯基)-乙酸
• 英文名称: (2,4,6-Trimethylbenzene)-1,3,5-triacetic acid
• 英文别名: 2,4,6-Trimethylbenzene-1,3,5-triacetic acid；(3,5-Bis-carboxymethyl-2,4,6-trimethyl-phenyl)-acetic acid；2-[3,5-bis(carboxymethyl)-2,4,6-trimethylphenyl]acetic acid
• CAS: 40207-09-8
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: DCUDJNRYVIOFHP-UHFFFAOYSA-N

物化性质

• 熔点：
  283-285℃
• 沸点：
  554℃
• 密度：
  1.334
• 闪点：
  303℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2917399090

反应信息

• 作为反应物：
  描述：

  2,4,6-三甲基-1,3,5-苯三乙酸 在 氯化亚砜 作用下， 生成 2-[3,5-Bis(2-chloro-2-oxoethyl)-2,4,6-trimethylphenyl]acetyl chloride
  参考文献：
  名称：

  基于无环吡啶基受体的碳水化合物的分子识别

  摘要：

  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。

  DOI：

  10.1021/jo048979k
• 作为产物：
  描述：

  2,4,6-三溴甲基三甲基苯 在 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 38.0h， 生成 2,4,6-三甲基-1,3,5-苯三乙酸
  参考文献：
  名称：

  Topological Correspondence Between Crystal Structure of 2,4,6-Trimethylbenzene-1,3,5-tris(methanaminium) 2,4,6-Trimethylbenzene-1,3,5-triacetate and Cesium Chloride

  摘要：

  2,4,6-三甲基苯-1,3,5-三(甲胺) 2,4,6-三甲基苯-1,3,5-三乙酸盐通过氢键介导固态自组装。它形成了三维氢键网络，其中每个三阳离子与八个三阴离子协同作用，反之亦然。所得到的晶体结构在拓扑上对应于简单的无机氯化铯型结构。

  DOI：

  10.1135/cccc20001587

文献信息

• 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。
• Artificial Receptors That Provides a Preorganized Hydrophobic Environment:  A Biomimetic Approach to Dopamine Recognition in Water
  作者：Jeongryul Kim、Balamurali Raman、Kyo Han Ahn

  DOI：10.1021/jo051630s

  日期：2006.1.1

  oxazoline-based artificial receptors, capable of providing a preorganized hydrophobic environment by rational design, which mimics a hydrophobic pocket predicted for a human D2 receptor. The receptors show an amphiphilic nature owing to the presence of hydrophilic sulfonate groups at the periphery of the tripodal oxazoline ligands, which seems to contribute in forming the preorganized hydrophobic environment

  水中多巴胺的识别已通过基于三脚架恶唑啉的人工受体实现，该人工受体能够通过合理的设计提供一个预先组织好的疏水环境，该环境模仿了人类D2受体的疏水口袋。由于三脚架恶唑啉配体的外围存在亲水性磺酸盐基团，因此该受体具有两亲性质，这似乎有助于形成预先组织好的疏水环境。人工受体识别水中多巴胺盐酸盐之间的各种有机铵客人合理的选择性。观察到的受体的结合行为是通过在预先组织好的疏水性口袋状环境中引起客体包涵而不是通​​过简单的离子对相互作用来解释的。理性预测1：1种夹杂物的结合模式受到结合研究（例如无法提供相似结合口袋的参考受体），Job和VT-NMR实验，电喷雾电离质量分析和客体选择性数据的支持。这项研究表明，即使从无环的小分子人工受体也可以产生有效的疏水环境。在生物系统中使用的这种预先组织的疏水环境可以有效地用作互补的结合力，以识别有机铵客人，例如水中的多巴胺盐酸盐。这项研究表明，即使从无环的小分子人工
• Enantioselective Michael addition catalyzed by chiral tripodal oxazoline–tBuOK complexes
  作者：Sung-Gon Kim、Kyo Han Ahn

  DOI：10.1016/s0040-4039(01)00681-5

  日期：2001.6

  Benzene-based tripodal oxazolines are found to be novel chiral ligands for the catalytic enantioselective Michael addition via potassium enolates. Thus, methyl phenylacetate undergoes 1,4-addition to methyl acrylate using a catalytic amount of a tBuOK–oxazoline complex in toluene at −78°C, and up to 82% ee is obtained.

  发现基于苯的三脚架恶唑啉是经由烯醇钾催化对映选择性迈克尔加成的新型手性配体。因此，在-78°C下，使用催化量的t BuOK-恶唑啉络合物在甲苯中的催化量，将乙酸苯酯甲酯加成1，4-丙烯酸甲酯，并获得高达82％的ee。
• Novel Artificial Receptors for Alkylammonium Ions with Remarkable Selectivity and Affinity
  作者：Sung-Gon Kim、Kyo Han Ahn

  DOI：10.1002/1521-3765(20000915)6:18<3399::aid-chem3399>3.0.co;2-m

  日期：2000.9.15

  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.
• Secondary Building Unit (SBU) Controlled Formation of a Catalytically Active Metal–Organic Polyhedron (MOP) Derived from a Flexible Tripodal Ligand
  作者：Mithun Paul、N. N. Adarsh、Parthasarathi Dastidar

  DOI：10.1021/cg4018322

  日期：2014.3.5

  A nanosized truncated octahedron-shaped metal-organic-polyhedron (MOP) namely [Cu-12(TMBTA)(8)(DMA)(4)(H2O)(8)}center dot 8H(2)O center dot X] MOP-TO (X = 48 H2O molecules as per SQUEEZE calculation and TGA data) was successfully derived from a flexible C-3-symmetric ligand (2,4,6-trimethylbenzene)-1,3,5-triacetic acid (TMBTA) and Cu(NO3)(2) in dimethyl acetamide (DMA) and EtOH under solvothermal conditions. The nanocage was well-characterized by single crystal X-ray diffraction (SXRD) and electron spray ionization mass spectrometry (ESI-MS). Remarkably, the nanocage molecules could be seen under high-resolution transmission electron microscope (HR-TEM). It was evident that the Cu(II) paddle wheel secondary building unit (CPWSBU) was responsible for the formation of the nanocage, as the corresponding reactions of TMBTA with other metal ions (e.g., Co(II) and Zn(II) resulted in the formation of two coordination polymers, namely [Co(mu-TMBTA)-(H2O)(4)}](alpha) TMBTA-Co(II) and [(H2O)(2)Zn(mu-TMBTA)Zn center dot K}center dot 2H(2)O](alpha) TMBTA-Zn(II). Interestingly, the nanocage MOP-TO was exploited in catalyzing (2,2,6,6-tetramethylpiperidin-1-yl)oxy (TEMPO)-assisted aerobic oxidation of benzyl alcohol to benzaldehyde.