(5S,10S)-5,10-bis(2-methylpropyl)-3,12-dioxa-6,9,18-triazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,7,8,13-tetraone | 1597413-16-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (5S,10S)-5,10-bis(2-methylpropyl)-3,12-dioxa-6,9,18-triazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,7,8,13-tetraone
• 英文别名: (5S,10S)-5,10-bis(2-methylpropyl)-3,12-dioxa-6,9,18-triazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,7,8,13-tetrone
• CAS: 1597413-16-5
• 化学式: C₂₁H₂₉N₃O₆
• 分子量: 419.478
• InChiKey: SBCZSRCRQPBIBV-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S,10S)-5,10-bis(2-methylpropyl)-3,12-dioxa-6,9,18-triazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,7,8,13-tetraone 、 (S)-α-(1-naphthyl)ethylammonium perchlorate 以 氘代二甲亚砜 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide–diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts

  摘要：

  Four novel C-2-symmetric macrocyclic compounds with a pyridine function and possessing amide and ester lingeages were prepared. The enantiomeric discrimination abilities of these macrocycles against alpha-phenylethylammonium and alpha-(1-naphthyl)ethylammonium perchlorate salts were measured by standard H-1 NMR titration techniques in DMSO-d(6). A binding constant ratio of 31 (Kbind(S)/Kbind(R)) for two enantiomers of alpha-(1-naphthyl)ethylammonium salt with the macrocyclic host (S,S)-4 bearing phenyl arms was observed, which corresponds to an enantiomeric discrimination of approximately 94%. Molecular dynamic calculations were performed for some of the supramolecular complexes to in order to gain insight into the mode of molecular recognition between the macrocyclic compounds and ammonium salts; these results were consistent with experimental observations, which may be relevant to those in biochemical processes occurring in organisms. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.009
• 作为产物：
  描述：

  2,6-氯甲酰吡啶 、 N,N'-双[(2S)-1-羟基-4-甲基戊-2-基]草酰胺 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 120.0h， 以44%的产率得到(5S,10S)-5,10-bis(2-methylpropyl)-3,12-dioxa-6,9,18-triazabicyclo[12.3.1]octadeca-1(18),14,16-triene-2,7,8,13-tetraone
  参考文献：
  名称：

  Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide–diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts

  摘要：

  Four novel C-2-symmetric macrocyclic compounds with a pyridine function and possessing amide and ester lingeages were prepared. The enantiomeric discrimination abilities of these macrocycles against alpha-phenylethylammonium and alpha-(1-naphthyl)ethylammonium perchlorate salts were measured by standard H-1 NMR titration techniques in DMSO-d(6). A binding constant ratio of 31 (Kbind(S)/Kbind(R)) for two enantiomers of alpha-(1-naphthyl)ethylammonium salt with the macrocyclic host (S,S)-4 bearing phenyl arms was observed, which corresponds to an enantiomeric discrimination of approximately 94%. Molecular dynamic calculations were performed for some of the supramolecular complexes to in order to gain insight into the mode of molecular recognition between the macrocyclic compounds and ammonium salts; these results were consistent with experimental observations, which may be relevant to those in biochemical processes occurring in organisms. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.009

文献信息

• Synthesis of rigid and C2-symmetric pyridino-15-crown-5 type macrocycles bearing diamide–diester functions: enantiomeric recognition for chiral primary organoammonium perchlorate salts
  作者：Sevil Şeker、Deniz Barış、Nevin Arslan、Yılmaz Turgut、Necmettin Pirinççioğlu、Mahmut Toğrul

  DOI：10.1016/j.tetasy.2014.01.009

  日期：2014.3

  Four novel C-2-symmetric macrocyclic compounds with a pyridine function and possessing amide and ester lingeages were prepared. The enantiomeric discrimination abilities of these macrocycles against alpha-phenylethylammonium and alpha-(1-naphthyl)ethylammonium perchlorate salts were measured by standard H-1 NMR titration techniques in DMSO-d(6). A binding constant ratio of 31 (Kbind(S)/Kbind(R)) for two enantiomers of alpha-(1-naphthyl)ethylammonium salt with the macrocyclic host (S,S)-4 bearing phenyl arms was observed, which corresponds to an enantiomeric discrimination of approximately 94%. Molecular dynamic calculations were performed for some of the supramolecular complexes to in order to gain insight into the mode of molecular recognition between the macrocyclic compounds and ammonium salts; these results were consistent with experimental observations, which may be relevant to those in biochemical processes occurring in organisms. (C) 2014 Elsevier Ltd. All rights reserved.