(4-perfluorohexylsulfanyl-phenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 551935-38-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4-perfluorohexylsulfanyl-phenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexylsulfanyl)phenoxy]oxan-2-yl]methyl acetate
• CAS: 551935-38-7
• 化学式: C₂₆H₂₃F₁₃O₁₀S
• 分子量: 774.508
• InChiKey: AEJPKSJBHIUUFU-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (4-perfluorohexylsulfanyl-phenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到p-perfluorohexylsulfanyl-phenyl-β-D-glucopyranoside
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents

  摘要：

  The perfluorohexyl-aryl-thioethers 3 and 4, building blocks for the synthesis of the chiral target mesogens 12-15, were prepared by dithionite-mediated S-perfluoroalkylation of the p-substituted thiophenols 1 and 2. The phenolic HO- group of 3 was O-glucosylated with pentaacetyl-D-glucopyranose to 5 followed by deacetylation forming the tetrol 6 and by acetalizing with 4-(4-perfluorohexylsulfanylbenzoyloxy)-benzaldehyde-dimethylacetal (8) generating the dihydroxy-intermediate 9. The latter contains two perfluorohexylthio chains. Alternatively, the dimethylacetal 8 was linked to p-octylphenyl-beta-(D)-glucopyranoside (10) giving the mixed octyl/perfluorohexyl substituted p-octylphenyl-4,6-O-[4'-(4"-perfluorohexylsulfanyl)-benzoyloxy]-benzylidene-beta-(D)-glucopyranoside (11). Compound 8 was obtained via esterification of 4 with p-hydroxy-benzaldehyde to 4-(4-perfluorohexylsulfanyl-benzoyloxy)-benzaldehyde (7). Finally, the diols 9 and 11 were dehydroxylated to 12 and 13 followed by hydrogenation yielding 14 and 15, respectively. Tetrol 6, diols 9, 11 and the non-amphiphilic compounds 7, 12-15 are thermotropic liquid crystals. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00310-x
• 作为产物：
  描述：

  全氟己基碘烷 在 sodium dithionite 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 (4-perfluorohexylsulfanyl-phenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents

  摘要：

  The perfluorohexyl-aryl-thioethers 3 and 4, building blocks for the synthesis of the chiral target mesogens 12-15, were prepared by dithionite-mediated S-perfluoroalkylation of the p-substituted thiophenols 1 and 2. The phenolic HO- group of 3 was O-glucosylated with pentaacetyl-D-glucopyranose to 5 followed by deacetylation forming the tetrol 6 and by acetalizing with 4-(4-perfluorohexylsulfanylbenzoyloxy)-benzaldehyde-dimethylacetal (8) generating the dihydroxy-intermediate 9. The latter contains two perfluorohexylthio chains. Alternatively, the dimethylacetal 8 was linked to p-octylphenyl-beta-(D)-glucopyranoside (10) giving the mixed octyl/perfluorohexyl substituted p-octylphenyl-4,6-O-[4'-(4"-perfluorohexylsulfanyl)-benzoyloxy]-benzylidene-beta-(D)-glucopyranoside (11). Compound 8 was obtained via esterification of 4 with p-hydroxy-benzaldehyde to 4-(4-perfluorohexylsulfanyl-benzoyloxy)-benzaldehyde (7). Finally, the diols 9 and 11 were dehydroxylated to 12 and 13 followed by hydrogenation yielding 14 and 15, respectively. Tetrol 6, diols 9, 11 and the non-amphiphilic compounds 7, 12-15 are thermotropic liquid crystals. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00310-x