(10R,11R)-(-)-10-methyl-3,6,9-trioxa-1,11-dodecanediol | 133673-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (10R,11R)-(-)-10-methyl-3,6,9-trioxa-1,11-dodecanediol
• 英文别名: (2R,3R)-3-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]butan-2-ol
• CAS: 133673-60-6
• 化学式: C₁₀H₂₂O₅
• 分子量: 222.282
• InChiKey: PRLRSBLHAUSFSJ-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,6-bis[(tosyloxy)methyl]pyridine 、 (10R,11R)-(-)-10-methyl-3,6,9-trioxa-1,11-dodecanediol 在 sodium hydride 作用下， 生成 (4R,5R)-(-)-4,5-dimethyl-3,6,9,12,15-pentaoxa-21-azabicyclo<15.3.1>heneicosa-1(21),17,19-triene
  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：

  三乙二醇 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 水 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 溶剂黄146 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 100.0h， 生成 (10R,11R)-(-)-10-methyl-3,6,9-trioxa-1,11-dodecanediol
  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