(S,S)-(+)-1,11-di-tert-butyl-3,6,9-trioxaundecane-1,11-diol | 133673-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S,S)-(+)-1,11-di-tert-butyl-3,6,9-trioxaundecane-1,11-diol
• 英文别名: (2S)-1-[2-[2-[(2S)-2-hydroxy-3,3-dimethylbutoxy]ethoxy]ethoxy]-3,3-dimethylbutan-2-ol
• CAS: 133673-59-3
• 化学式: C₁₆H₃₄O₅
• 分子量: 306.443
• InChiKey: UUKGYGKGIRPEOC-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  吡啶-2.6-二羧酸二甲酯 、 (S,S)-(+)-1,11-di-tert-butyl-3,6,9-trioxaundecane-1,11-diol 在 4 A molecular sieve 、 sodium methylate 作用下， 以 苯 为溶剂， 以15%的产率得到(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
• 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 作用下， 以 二氯甲烷 为溶剂， 生成 (S,S)-(+)-1,11-di-tert-butyl-3,6,9-trioxaundecane-1,11-diol
  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

• Enantioseparation of racemic organic ammonium perchlorates by a silica gel bound optically active di-tert-butylpyridino-18-crown-6 ligand
  作者：Zoltán Köntös、Péter Huszthy、Jerald S. Bradshaw、Reed M. Izatt

  DOI：10.1016/s0957-4166(99)00163-9

  日期：1999.6

  Both enantiomers of the novel chiral di-tert-butylpyridino-18-crown-6 ligand (R,R)-7 and (S,S)-7 containing an allyloxy group on the pyridine subcyclic unit were prepared by the reaction of 4-allyloxy-2,6-pyridinedimethyl ditosylate 9 and the enantiomers of di-tert-butyl-substituted tetraethylene glycol (R,R)-8 and (S,S)-8 in the presence of a strong base. One of them, (R,R)-7, was covalently attached to silica gel, and this chiral stationary phase (CSP) separated four selected racemic organic ammonium perchlorates into their enantiomers by column chromatography. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.