(4R)-4-methyl-2-[[2,4,6-trimethyl-3,5-bis[[(4R)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]methyl]phenyl]methyl]-4,5-dihydro-1,3-oxazole | 264187-28-2

• 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: (4R)-4-methyl-2-[[2,4,6-trimethyl-3,5-bis[[(4R)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]methyl]phenyl]methyl]-4,5-dihydro-1,3-oxazole
• CAS: 264187-28-2
• 化学式: C₂₄H₃₃N₃O₃
• 分子量: 411.544
• InChiKey: NNERVXNVNTURMM-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-苯甘氨醇 、 (4R)-4-methyl-2-[[2,4,6-trimethyl-3,5-bis[[(4R)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]methyl]phenyl]methyl]-4,5-dihydro-1,3-oxazole 在 zinc(II) chloride 作用下， 以 氯苯 为溶剂， 反应 6.0h， 以34%的产率得到(4R,4'R)-2,2'-((2,4,6-Trimethyl-5-(((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methyl)-1,3-phenylene)bis(methylene))bis(4-methyl-4,5-dihydrooxazole)
  参考文献：
  名称：

  Synthesis of C1-symmetric chiral tripodal oxazolines through an oxazoline exchange reaction with amino alcohols

  摘要：

  Various C-1-symmetric chiral tripodal tris(oxazolines) with two different oxazoline units were synthesized from chiral C-3-symmetric tris(oxazolines) through an oxazoline exchange reaction with amino alcohols in the presence of zinc chloride. Evaluation of the new oxazolines as chiral molecular receptor showed that some of the receptors have chiral discrimination ability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.107
• 作为产物：
  描述：

  2-{3,5-Bis-[((R)-2-chloro-1-methyl-ethylcarbamoyl)-methyl]-2,4,6-trimethyl-phenyl}-N-((R)-2-chloro-1-methyl-ethyl)-acetamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (4R)-4-methyl-2-[[2,4,6-trimethyl-3,5-bis[[(4R)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]methyl]phenyl]methyl]-4,5-dihydro-1,3-oxazole
  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

文献信息

• Selective Recognition of NH₄⁺over K⁺with Tripodal Oxazoline Receptors
  作者：Kyo Han Ahn、Sung-Gon Kim、Junyang Jung、Kyung-Hyun Kim、Jaheon Kim、Jik Chin、Kimoon Kim

  DOI：10.1246/cl.2000.170

  日期：2000.2

  Benzene-based tripodal tris(oxazolines) are found to be promising receptors for the selective recognition of NH4+ over K+ with high binding affinities.

  研究发现，苯基三元三（恶唑啉）是一种很有前途的受体，可选择性地识别 NH4+ 而不是 K+，并具有很高的结合亲和力。
• Synthesis of C1-symmetric chiral tripodal oxazolines through an oxazoline exchange reaction with amino alcohols
  作者：Sung-Gon Kim、Hye Ran Seong、Jeongryul Kim、Kyo Han Ahn

  DOI：10.1016/j.tetlet.2004.07.107

  日期：2004.9

  Various C-1-symmetric chiral tripodal tris(oxazolines) with two different oxazoline units were synthesized from chiral C-3-symmetric tris(oxazolines) through an oxazoline exchange reaction with amino alcohols in the presence of zinc chloride. Evaluation of the new oxazolines as chiral molecular receptor showed that some of the receptors have chiral discrimination ability. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.