N-(β-D-glucopyranosyl)-N-(4-butyl-4-phenyl)acrylamide | 201482-04-4

• 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-(4-butyl-4-phenyl)acrylamide
• 英文别名: N-(4-phenylbutyl)-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]prop-2-enamide
• CAS: 201482-04-4
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: DYGLQPNOJRYNNK-IQZDNPOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  乙酰氯 、 N-(β-D-glucopyranosyl)-N-(4-butyl-4-phenyl)acrylamide 以 吡啶 为溶剂， 反应 1.0h， 以69.6%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-phenylbutyl(prop-2-enoyl)amino]oxan-2-yl]methyl acetate
  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
• 作为产物：
  描述：

  苯基-4-丁胺 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-(4-butyl-4-phenyl)acrylamide
  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.