N-(β-D-glucopyranosyl)-N-dodecylacrylamide | 201482-02-2

• 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-dodecylacrylamide
• 英文别名: N-dodecyl-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]prop-2-enamide
• CAS: 201482-02-2
• 化学式: C₂₁H₃₉NO₆
• 分子量: 401.544
• InChiKey: FHSFDGLGUJMUCE-QNDFHXLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  二氮杂18-冠醚-6 、 N-(β-D-glucopyranosyl)-N-dodecylacrylamide 在 2,4-二叔丁基苯酚 、 四甲基氢氧化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 168.0h， 以70%的产率得到7,16-bis[N-β-D-glucopyranosyl-N-dodecyl-2-(carboxamidoethyl)]-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
  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：

  十二烷基伯胺 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-dodecylacrylamide
  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

• 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