4-(4-perfluorohexylsulfanyl-benzyloxy)-benzaldehyde-dimethylacetal | 551935-41-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(4-perfluorohexylsulfanyl-benzyloxy)-benzaldehyde-dimethylacetal
• 英文别名: [4-(dimethoxymethyl)phenyl] 4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexylsulfanyl)benzoate
• CAS: 551935-41-2
• 化学式: C₂₂H₁₅F₁₃O₄S
• 分子量: 622.404
• InChiKey: ZNYLLAMHWRAFPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(4-perfluorohexylsulfanyl-benzyloxy)-benzaldehyde-dimethylacetal 在 咪唑 、 甲烷磺酸 、 tri-iodoimidazole 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 xylene 为溶剂， 60.0~130.0 ℃ 、4.5 kPa 条件下， 反应 6.0h， 生成 (4-octylphenyl)-(R)-4,6-O-[4'-(4-perfluorohexylsulfanyl)-benzoyloxy]-benzylidene-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
  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：

  甲醇 、 4-(4-perfluorohexylsulfanyl-benzyloxy)-benzaldehyde 在 Amberlite IR-120 、 原甲酸三甲酯 作用下， 反应 4.0h， 以98.4%的产率得到4-(4-perfluorohexylsulfanyl-benzyloxy)-benzaldehyde-dimethylacetal
  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