2-[3,5-Bis(2-chloro-2-oxoethyl)-2,4,6-trimethylphenyl]acetyl chloride | 797818-06-5

• 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: 2-[3,5-Bis(2-chloro-2-oxoethyl)-2,4,6-trimethylphenyl]acetyl chloride
• CAS: 797818-06-5
• 化学式: C₁₅H₁₅Cl₃O₃
• 分子量: 349.641
• InChiKey: QGVJBFGXADHVEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[3,5-Bis(2-chloro-2-oxoethyl)-2,4,6-trimethylphenyl]acetyl chloride 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 30.0h， 生成 2-{3,5-Bis-[(2-chloro-ethylcarbamoyl)-methyl]-2,4,6-trimethyl-phenyl}-N-(2-chloro-ethyl)-acetamide
  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：

  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

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。
• 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
• 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.