1-amino-1-deoxy-N-(2-hydroxy-4,4,5,5,6,6,7,7,7-nonafluoroheptyl)-N-methyl-D-glucitol | 1232237-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-amino-1-deoxy-N-(2-hydroxy-4,4,5,5,6,6,7,7,7-nonafluoroheptyl)-N-methyl-D-glucitol
• 英文别名: [N-Me-D-glucamine-N-yl]-CH2CH(OH)CH2-C4F9；(2R,3R,4R,5S)-6-[methyl-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)amino]hexane-1,2,3,4,5-pentol
• CAS: 1232237-23-8
• 化学式: C₁₄H₂₂F₉NO₆
• 分子量: 471.317
• InChiKey: YEDXIMZZNUAVSJ-DEMCRKGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  30
• 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：
  125
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  N-甲基-D-葡胺 、 3-(全氟正丁烷)-1,2-环氧丙烷 以 乙醇 为溶剂， 反应 6.0h， 以91%的产率得到1-amino-1-deoxy-N-(2-hydroxy-4,4,5,5,6,6,7,7,7-nonafluoroheptyl)-N-methyl-D-glucitol
  参考文献：
  名称：

  Perfluoroalkylated derivatives of 6-deoxy-6-ethylamino-d-galactose, 1-deoxy-1-methylamino-d-glucitol, and 1-amino-1-deoxy-d-glucitol: syntheses, hemocompatibility, and effect on perfluorocarbon emulsion

  摘要：

  N-Polyfluoroalkyl derivatives of 6-deoxy-6-ethylamino-1,2,3,4-di-O-isopropylidene-alpha-D-galactopyranose (8-10), 1-deoxy-1-methylamino-D-glucitol (13-15), and 1-amino-1-deoxy-D-glucitol (16-18), all possessing perfluoroalkyl segment, were prepared using nucleophilic epoxide ring opening of 2-[(perfluoroalkyl)methyl] oxiranes 1-3. Co-emulsifying properties and hemolytic activity of the new perfluoroalkylated amphiphiles were tested. Both types of the polyol derivatives 8-10 and 13-18 generally displayed good to excellent co-emulsifying properties on testing on perfluorodecalin/Pluronic F-68 microemulsions Mono-perfluoroalkylated compounds 8-10 and 13-15 displayed high hemolysis, whereas acyclic bis-perfluoroalkylated compounds 16-18 were non-hemolytic even for short perfluorobutyl segment (16) The properties were generally improving with increasing perfluoroalkyl chain length. (C) 2010 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.carres.2010.03.023

文献信息

• Perfluoroalkylated derivatives of 6-deoxy-6-ethylamino-d-galactose, 1-deoxy-1-methylamino-d-glucitol, and 1-amino-1-deoxy-d-glucitol: syntheses, hemocompatibility, and effect on perfluorocarbon emulsion
  作者：Robert Kaplánek、Radek Polák、Oldřich Paleta、Karel Kefurt、Jitka Moravcová、Iva Křenová、Milan Kodíček

  DOI：10.1016/j.carres.2010.03.023

  日期：2010.5

  N-Polyfluoroalkyl derivatives of 6-deoxy-6-ethylamino-1,2,3,4-di-O-isopropylidene-alpha-D-galactopyranose (8-10), 1-deoxy-1-methylamino-D-glucitol (13-15), and 1-amino-1-deoxy-D-glucitol (16-18), all possessing perfluoroalkyl segment, were prepared using nucleophilic epoxide ring opening of 2-[(perfluoroalkyl)methyl] oxiranes 1-3. Co-emulsifying properties and hemolytic activity of the new perfluoroalkylated amphiphiles were tested. Both types of the polyol derivatives 8-10 and 13-18 generally displayed good to excellent co-emulsifying properties on testing on perfluorodecalin/Pluronic F-68 microemulsions Mono-perfluoroalkylated compounds 8-10 and 13-15 displayed high hemolysis, whereas acyclic bis-perfluoroalkylated compounds 16-18 were non-hemolytic even for short perfluorobutyl segment (16) The properties were generally improving with increasing perfluoroalkyl chain length. (C) 2010 Elsevier Ltd. All rights reserved