(9S,14S)-9,14-bis[(2S)-butan-2-yl]-1,4,7-trioxa-10,13-diazacyclopentadecane-2,6,11,12-tetrone | 1019203-02-1

• 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,14S)-9,14-bis[(2S)-butan-2-yl]-1,4,7-trioxa-10,13-diazacyclopentadecane-2,6,11,12-tetrone
• CAS: 1019203-02-1
• 化学式: C₁₈H₃₀N₂O₇
• 分子量: 386.445
• InChiKey: VLDHBLYEKXOBFR-IGQOVBAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N'-bis[(1S)-1-(S)-sec-butyl-2-hydroxyethyl]ethanediamide 、 2,2'-氧化二乙酰氯 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(9S,14S)-9,14-bis[(2S)-butan-2-yl]-1,4,7-trioxa-10,13-diazacyclopentadecane-2,6,11,12-tetrone
  参考文献：
  名称：

  Novel C₂-Symmetric Macrocycles Bearing Diamide−Diester Groups:  Synthesis and Enantiomeric Recognition for Primary Alkyl Ammonium Salts

  摘要：

  We synthesized a series of novel macrocycles with diamide-diester groups (S,S)-1, (S,S)-2, (S,S)-3, and (R,R)-1, derived from dimethyloxalate and amino alcohols by high dilution technique, and evaluated enantiomeric recognition properties of these macrocycles toward primary alkyl ammonium salts by H-1 NMR titration. Taking into account the host employed, important differences were observed in the K-a values of (R)-Am and (S)-Am for (S,S)-1 and (R,R)-1 hosts, K-S/K-R = 5.55 and K-R/K-S = 3.65, Delta Delta G(o) = 0.43 and -0.32 kJ mol(-1), respectively. There seems a general tendency for the host to include the guests with the same absolute configuration.

  DOI：

  10.1021/jo702210c

文献信息

• Novel <i>C</i>₂-Symmetric Macrocycles Bearing Diamide−Diester Groups:  Synthesis and Enantiomeric Recognition for Primary Alkyl Ammonium Salts
  作者：Murat Sunkur、Deniz Baris、Halil Hosgoren、Mahmut Togrul

  DOI：10.1021/jo702210c

  日期：2008.4.1

  We synthesized a series of novel macrocycles with diamide-diester groups (S,S)-1, (S,S)-2, (S,S)-3, and (R,R)-1, derived from dimethyloxalate and amino alcohols by high dilution technique, and evaluated enantiomeric recognition properties of these macrocycles toward primary alkyl ammonium salts by H-1 NMR titration. Taking into account the host employed, important differences were observed in the K-a values of (R)-Am and (S)-Am for (S,S)-1 and (R,R)-1 hosts, K-S/K-R = 5.55 and K-R/K-S = 3.65, Delta Delta G(o) = 0.43 and -0.32 kJ mol(-1), respectively. There seems a general tendency for the host to include the guests with the same absolute configuration.