N-(1-octyl)-D-gulonamide | 114275-85-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(1-octyl)-D-gulonamide
• 英文别名: N-(n-Octyl)-D-gulonamide；N-(octyl)-D-gulonamide；(2R,3R,4S,5R)-2,3,4,5,6-pentahydroxy-N-octylhexanamide
• CAS: 114275-85-3
• 化学式: C₁₄H₂₉NO₆
• 分子量: 307.387
• InChiKey: KTMBZDQOFPBYBL-YVECIDJPSA-N

物化性质

• 沸点：
  631.5±55.0 °C(predicted)
• 密度：
  1.207±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  130
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-gulo-1,5-lactone 、 辛胺 以 甲醇 为溶剂， 生成 N-(1-octyl)-D-gulonamide
  参考文献：
  名称：

  The crystal packing of N-(n-octyl)-d-gulonamide containing tail-to-tail sheets compared to its gluconamide diastereomer showing head-to-tail arrangement

  摘要：

  N-Octylamides of diastereomeric gluconic and gulonic acids form molecular aggregates of extremely different curvature, namely helical micellar rods with a diameter of 4 nm and planar bilayers. In the crystal structure of the gulonamide compound, symmetric ''tail-to-tail'' bilayer sheets are observed, whereas the gluconamide derivative (whose crystal structure was determined previously) forms an unusual ''head-to-tail'' arrangement. These differences are unexpected because both diastereomers contain one pair each of syn- and anti-oriented hydroxyl groups in 1,3-positions of the extended aldonic acid chains. The experimental results are explained by the occurrence of hydrogen-bond patterns between hydroxyl groups, either within one crystal sheet or hydrophobic bilayer (gluconamide) or between the end groups of neighboring sheets (gulonamide).

  DOI：

  10.1016/s0008-6215(00)90511-1