(2S)-2-methyl-3,6,9,12-tetraoxa-15,22-diazatricyclo[13.7.0.016,21]docosa-1(22),16,18,20-tetraene | 1447023-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (2S)-2-methyl-3,6,9,12-tetraoxa-15,22-diazatricyclo[13.7.0.016,21]docosa-1(22),16,18,20-tetraene
• CAS: 1447023-07-5
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: UHNCBMDNTKBKCY-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-methyl-3,6,9,12-tetraoxa-15,22-diazatricyclo[13.7.0.016,21]docosa-1(22),16,18,20-tetraene 、 (S)-α-phenylethylammonium perchlorate 以 乙腈 为溶剂， 生成 perchloric acid compound with (S)-1-phenylethan-1-amine and (S)-1-methyl-3,4,6,7,9,10,12,13-octahydro-1H-benzo[4,5]imidazo[2,1-l][1,4,7,10]tetraoxa[13]azacyclopentadecine (1:1:1)
  参考文献：
  名称：

  Chiral benzimidazole-derived mono azacrowns: synthesis and enantiomer recognition studies with chiral amines and their ammonium salts

  摘要：

  Benzimidazole fused chiral mono aza-15-crown-5 2, was obtained in a single step from (S)-(-)-2-(alpha-hydroxyethyl) benzimidazole 1. This new class of aza-crown has a unique structure with the chiral unit being held in a stable conformation due to adjacent benzimidazole ring contributing to its stereodiscrimination ability. The interactions between the host aza-crown and enantiomerically pure amine guests in ionic and neutral forms exhibited the enantio-discrimination ability. The preliminary evaluation of the chiral sensing was monitored using H-1 NMR and circular dichroism (CD) analysis of the complexes at their molar equivalence. The binding parameters were determined using electronic absorption spectroscopy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.021
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 (alphas)-(9ci)-alpha-甲基-1H-苯并咪唑-2-甲醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 以48%的产率得到(2S)-2-methyl-3,6,9,12-tetraoxa-15,22-diazatricyclo[13.7.0.016,21]docosa-1(22),16,18,20-tetraene
  参考文献：
  名称：

  Chiral benzimidazole-derived mono azacrowns: synthesis and enantiomer recognition studies with chiral amines and their ammonium salts

  摘要：

  Benzimidazole fused chiral mono aza-15-crown-5 2, was obtained in a single step from (S)-(-)-2-(alpha-hydroxyethyl) benzimidazole 1. This new class of aza-crown has a unique structure with the chiral unit being held in a stable conformation due to adjacent benzimidazole ring contributing to its stereodiscrimination ability. The interactions between the host aza-crown and enantiomerically pure amine guests in ionic and neutral forms exhibited the enantio-discrimination ability. The preliminary evaluation of the chiral sensing was monitored using H-1 NMR and circular dichroism (CD) analysis of the complexes at their molar equivalence. The binding parameters were determined using electronic absorption spectroscopy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.021