(4S,14S)-(+)-4,14-di-tert-butyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene-2,16-dione | 127102-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (4S,14S)-(+)-4,14-di-tert-butyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene-2,16-dione
• 英文别名: (4S,14S)-4,14-ditert-butyl-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]henicosa-1(21),17,19-triene-2,16-dione
• CAS: 127102-68-5
• 化学式: C₂₃H₃₅NO₇
• 分子量: 437.533
• InChiKey: DTQLAFIRAUWAFY-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-methyl-benzenesulfonic acid [(2S)-2-hydroxy-3,3-dimethyl-butyl]ester 在 4-甲基苯磺酸吡啶 4 A molecular sieve 、 sodium methylate 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (4S,14S)-(+)-4,14-di-tert-butyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene-2,16-dione
  参考文献：
  名称：

  Recognition by new symmetrically substituted chiral diphenyl- and di-tert-butylpyridino-18-crown-6 and asymmetrically substituted chiral dimethylpyridino-18-crown-6 ligands of the enantiomers of various organic ammonium perchlorates

  摘要：

  Three new chiral pyridino-18-crown-6 ligands have been prepared. These ligands contain either two phenyl, two tert-butyl, or two methyl substituents on chiral macroring carbon atoms. The chiral di-tert-butyl-substituted diester crown analogue was also prepared. The starting chiral di-tert-butyl-substituted tetraethylene glycol needed to prepare the two di-tert-butyl-substituted crowns was obtained from chiral tert-butyl-1,2-ethanediol, which was resolved from its bis(hydrogen phthalate) brucine salt. A high degree of chiral recognition in CD2Cl2 of the enantiomers of [alpha-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) was shown by the diphenyl- and di-tert-butyl-substituted crowns as measured by differences in the free energy of activation (DELTA-G(c) double-ended-dagger) values determined by temperature-dependent H-1 NMR spectroscopy. The diphenyl- and di-tert-butyl-substituted crowns also exhibited high chiral recognition for the enantiomers of NapEt and other chiral organic ammonium salts in methanol and methanol-chloroform mixtures as shown by a large difference in the log K values determined by a direct H-1 NMR technique.

  DOI：

  10.1021/jo00010a028

文献信息

• Recognition by new symmetrically substituted chiral diphenyl- and di-tert-butylpyridino-18-crown-6 and asymmetrically substituted chiral dimethylpyridino-18-crown-6 ligands of the enantiomers of various organic ammonium perchlorates
  作者：Peter Huszthy、Jerald S. Bradshaw、Cheng Y. Zhu、Reed M. Izatt、Shneior Lifson

  DOI：10.1021/jo00010a028

  日期：1991.5

  Three new chiral pyridino-18-crown-6 ligands have been prepared. These ligands contain either two phenyl, two tert-butyl, or two methyl substituents on chiral macroring carbon atoms. The chiral di-tert-butyl-substituted diester crown analogue was also prepared. The starting chiral di-tert-butyl-substituted tetraethylene glycol needed to prepare the two di-tert-butyl-substituted crowns was obtained from chiral tert-butyl-1,2-ethanediol, which was resolved from its bis(hydrogen phthalate) brucine salt. A high degree of chiral recognition in CD2Cl2 of the enantiomers of [alpha-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) was shown by the diphenyl- and di-tert-butyl-substituted crowns as measured by differences in the free energy of activation (DELTA-G(c) double-ended-dagger) values determined by temperature-dependent H-1 NMR spectroscopy. The diphenyl- and di-tert-butyl-substituted crowns also exhibited high chiral recognition for the enantiomers of NapEt and other chiral organic ammonium salts in methanol and methanol-chloroform mixtures as shown by a large difference in the log K values determined by a direct H-1 NMR technique.