5-((4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)oxy)-2-nitrobenzyl 1H-imidazole-1-carboxylate | 1548722-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-((4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)oxy)-2-nitrobenzyl 1H-imidazole-1-carboxylate
• CAS: 1548722-99-1
• 化学式: C₂₂H₁₄F₁₇N₃O₅
• 分子量: 723.343
• InChiKey: CQWFRNUYYCPIHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.14
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  96.49
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-((4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)oxy)-2-nitrobenzyl 1H-imidazole-1-carboxylate 在 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 26.33h， 生成 (2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-((((5-((4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)oxy)-2-nitrobenzyl)oxy)carbonyl)amino)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines

  摘要：

  Two new fluorous photolabile-protecting groups (FNBC and FNB) and a new base-labile protecting group (FOC) for the masking of amines are reported. The protecting groups survive a wide range of common reaction conditions used in oligosaccharide synthesis and render the attached molecules amenable to fluorous solid-phase extraction (FSPE). A glycosyl acceptor containing the FNB group is shown to be useful in the synthesis of carbohydrates tagged with free deactivated secondary amines.

  DOI：

  10.1021/ol500023y
• 作为产物：
  描述：

  4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl methanesulfonate 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成 5-((4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)oxy)-2-nitrobenzyl 1H-imidazole-1-carboxylate
  参考文献：
  名称：

  Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines

  摘要：

  Two new fluorous photolabile-protecting groups (FNBC and FNB) and a new base-labile protecting group (FOC) for the masking of amines are reported. The protecting groups survive a wide range of common reaction conditions used in oligosaccharide synthesis and render the attached molecules amenable to fluorous solid-phase extraction (FSPE). A glycosyl acceptor containing the FNB group is shown to be useful in the synthesis of carbohydrates tagged with free deactivated secondary amines.

  DOI：

  10.1021/ol500023y