(9S,17S)-9,17-diisobutyl-1,4,7,13-tetraoxa-10,16-diazacyclooctadecane-2,6,11,15-tetraone | 1252023-09-8

• 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: (9S,17S)-9,17-diisobutyl-1,4,7,13-tetraoxa-10,16-diazacyclooctadecane-2,6,11,15-tetraone
• 英文别名: (9S,17S)-9,17-bis(2-methylpropyl)-1,4,7,13-tetraoxa-10,16-diazacyclooctadecane-2,6,11,15-tetrone
• CAS: 1252023-09-8
• 化学式: C₂₀H₃₄N₂O₈
• 分子量: 430.499
• InChiKey: JKWPJNQMNHHKRP-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,2'-氧化二乙酰氯 、 N-((S)-1-Hydroxymethyl-3-methyl-butyl)-2-[((S)-1-hydroxymethyl-3-methyl-butylcarbamoyl)-methoxy]-acetamide 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 120.0h， 以32%的产率得到(9S,17S)-9,17-diisobutyl-1,4,7,13-tetraoxa-10,16-diazacyclooctadecane-2,6,11,15-tetraone
  参考文献：
  名称：

  Synthesis of rigid and C2-symmetric 18-crown-6 type macrocycles bearing diamide–diester groups: enantiomeric recognition for α-(1-naphthyl)ethylammonium perchlorate salts

  摘要：

  A series of rigid and chiral C-2-symmetric 18-crown-6 type macrocycles (S,S)-4, (S,S)-5, (S,S)-6 and (R,R)-2 bearing diamide-ester groups were synthesized. The binding properties of these macrocycles were examined for ot-(1-naphthypethylammonium perchlorates salts by an 1H NMR titration method. Taking into account the host employed, important differences were observed in the Ka values of (R)- and (S)-enantiomers of guests for macrocycles (S,S)-4 and (S,S)-6, Ks/KR = 3.6, and Ks/KR = 0.1 (KR/Ks = 10.3).6.,6,G= 3.19 and Delta Delta G= -5.77 kJ mol(-1), respectively. The results indicated excellent enantioselectivity of macrocyclic (S,S)-6 towards the enantiomers of alpha-(1-naphthyl)ethylammonium perchlorate salts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.051

文献信息

• Synthesis of rigid and C2-symmetric 18-crown-6 type macrocycles bearing diamide–diester groups: enantiomeric recognition for α-(1-naphthyl)ethylammonium perchlorate salts
  作者：Deniz Barış、Sevil Şeker、Halil Hoşgören、Mahmut Toğrul

  DOI：10.1016/j.tetasy.2010.05.051

  日期：2010.8

  A series of rigid and chiral C-2-symmetric 18-crown-6 type macrocycles (S,S)-4, (S,S)-5, (S,S)-6 and (R,R)-2 bearing diamide-ester groups were synthesized. The binding properties of these macrocycles were examined for ot-(1-naphthypethylammonium perchlorates salts by an 1H NMR titration method. Taking into account the host employed, important differences were observed in the Ka values of (R)- and (S)-enantiomers of guests for macrocycles (S,S)-4 and (S,S)-6, Ks/KR = 3.6, and Ks/KR = 0.1 (KR/Ks = 10.3).6.,6,G= 3.19 and Delta Delta G= -5.77 kJ mol(-1), respectively. The results indicated excellent enantioselectivity of macrocyclic (S,S)-6 towards the enantiomers of alpha-(1-naphthyl)ethylammonium perchlorate salts. (C) 2010 Elsevier Ltd. All rights reserved.