N-(β-D-glucopyranosyl)-N-octylacrylamide | 178261-62-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(β-D-glucopyranosyl)-N-octylacrylamide
• 英文别名: N-(beta-D-glucopyranosyl)-N-octylacrylamide；N-octyl-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]prop-2-enamide
• CAS: 178261-62-6
• 化学式: C₁₇H₃₁NO₆
• 分子量: 345.436
• InChiKey: ZPFTWPWASUUZPU-USACIQFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4,8,11-四氮杂环十四烷 、 N-(β-D-glucopyranosyl)-N-octylacrylamide 在 sodium hydroxide 、 sodium nitrite 作用下， 反应 15.0h， 以90%的产率得到N-octyl-3-[8-[3-[octyl-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-3-oxopropyl]-1,4,8,11-tetrazacyclotetradec-1-yl]-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]propanamide
  参考文献：
  名称：

  大环糖基表面活性剂：结合自我聚集和络合特性的嵌段分子。

  摘要：

  DOI：

  10.1002/anie.200353484
• 作为产物：
  描述：

  D-葡萄糖 在 sodium carbonate 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 0.42h， 生成 N-(β-D-glucopyranosyl)-N-octylacrylamide
  参考文献：
  名称：

  Synthesis, Structural Analysis, and Properties of N-Alkylglucosyl(meth)acrylamides:  New Reactive Sugar Surfactants

  摘要：

  New reactive-surfactants, N-alkylglucosylacrylamides and N-alkylglucosylmethacrylamides, are easily prepared in two steps from glucose without protection. The complete structural analysis of these compounds by 1D and 2D NMR spectroscopy shows the existence of a rotational isomerism that is strongly dependent on the steric hindrance of the carbonyl substituent: whatever the alkyl chain length, both endo and exo rotamers are observed for N-alkylglucosylacrylamides 1 while the endo rotamer is the sole species observed in the case of N-alkylglucosylmethacrylamides 2. For acrylamido derivatives 1, the exo-endo equilibrium is solvent-dependent: the endo isomer is favored in polar nonaqueous solvents (endo-exo isomeric ratio R = 70/30) while the equilibrium is shifted toward the exo rotamer in protic acidic medium (R = 50/50 in water and 80/20 in acidic medium). An intramolecular hydrogen bond is assumed to be responsible for the increased stability of the endo rotamer. Furthermore, for tetra-O-acetylated derivatives the exo rotamer becomes favored in aprotic solvents. Surface tension measurements demonstrate that N-octyl- to -tetradecyl-substituted compounds 1 and 2 are surfactants with critical micelle concentrations ranging from 1.2 x 10(-2) to 1.7 x 10(-5) mol/L.

  DOI：

  10.1021/jo971486d

文献信息

• Glycosylated particle of latex or of inorganic oxide and process for the
  申请人：Societe Prolabo

  公开号：US05814407A1

  公开（公告）日：1998-09-29

  The invention relates to a glycosylated particle of latex or of inorganic oxide, exhibiting functional radicals at the surface. At least a proportion of said functional radicals is joined to a glycosyl residue. The particles preferably consist either of polymers obtained by polymerization of ethylenically unsaturated monomers or of silica. The invention finds an application as a detection agent in biology.

  本发明涉及一种具有表面功能基团的乳胶或无机氧化物的糖基化颗粒。至少一部分所述功能基团连接到糖基残基。颗粒物质优选由聚合乙烯类不饱和单体得到的聚合物或硅胶组成。本发明在生物学中作为检测试剂应用。
• Particule de latex ou d'oxyde minéral glycosylée, procédé de préparation d'une telle particule et utilisation de celle-ci en tant qu'agent de détection biologique ou de chromatographie d'affinité
  申请人：MERCK EUROLAB S.A.

  公开号：EP0709402B1

  公开（公告）日：2002-06-26
• US5814407A
  申请人：——

  公开号：US5814407A

  公开（公告）日：1998-09-29
• Synthesis, Structural Analysis, and Properties of <i>N</i>-Alkylglucosyl(meth)acrylamides:  New Reactive Sugar Surfactants
  作者：Laurence Retailleau、Annabelle Laplace、Hélène Fensterbank、Chantal Larpent

  DOI：10.1021/jo971486d

  日期：1998.2.1

  New reactive-surfactants, N-alkylglucosylacrylamides and N-alkylglucosylmethacrylamides, are easily prepared in two steps from glucose without protection. The complete structural analysis of these compounds by 1D and 2D NMR spectroscopy shows the existence of a rotational isomerism that is strongly dependent on the steric hindrance of the carbonyl substituent: whatever the alkyl chain length, both endo and exo rotamers are observed for N-alkylglucosylacrylamides 1 while the endo rotamer is the sole species observed in the case of N-alkylglucosylmethacrylamides 2. For acrylamido derivatives 1, the exo-endo equilibrium is solvent-dependent: the endo isomer is favored in polar nonaqueous solvents (endo-exo isomeric ratio R = 70/30) while the equilibrium is shifted toward the exo rotamer in protic acidic medium (R = 50/50 in water and 80/20 in acidic medium). An intramolecular hydrogen bond is assumed to be responsible for the increased stability of the endo rotamer. Furthermore, for tetra-O-acetylated derivatives the exo rotamer becomes favored in aprotic solvents. Surface tension measurements demonstrate that N-octyl- to -tetradecyl-substituted compounds 1 and 2 are surfactants with critical micelle concentrations ranging from 1.2 x 10(-2) to 1.7 x 10(-5) mol/L.
• Macrocyclic Sugar-Based Surfactants: Block Molecules Combining Self-Aggregation and Complexation Properties
  作者：Chantal Larpent、Annabelle Laplace、Thomas Zemb

  DOI：10.1002/anie.200353484

  日期：2004.6.14