N,N'-dihexyl-D-glucaramide | 156016-06-7

• 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,N'-dihexyl-D-glucaramide
• 英文别名: (2S,3S,4S,5R)-N,N'-dihexyl-2,3,4,5-tetrahydroxyhexanediamide
• CAS: 156016-06-7
• 化学式: C₁₈H₃₆N₂O₆
• 分子量: 376.494
• InChiKey: DAVZYOXZCYGLRT-YHUYYLMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-dihexyl-D-glucaramide 、 丙酰氯 在 吡啶 作用下， 以74.12%的产率得到2,3,4,5-tetra-O-propanoyl-N,N'-dihexyl-D-glucaramide
  参考文献：
  名称：

  MM3 Conformational Analysis and X‐ray Crystal Structure of 2,3,4,5‐Tetra‐O‐Acetyl‐N,N′‐Dimethyl‐D‐Glucaramide as a Conformational Model for the d‐Glucaryl Unit of Poly(Alkylene 2,3,4,5‐Tetra‐O‐Acetyl‐d‐Glucaramides)

  摘要：

  This report describes the MM3 conformational analysis and X-ray crystal structure of tetra-O-acetyl-N,N'-dimethyl-D-glucaramide as a conformational model for the D-glucaryl monomer unit of poly(alkylene tetra-O-acyl-glucaramides). The driving force for this study was to determine the conformational preferences for the diacid unit as a function of the increasing steric bulk of pendant O-acyl groups: acetyl, propanoyl, 2-methylpropanoyl, and 2,2-dimethylpropanoyl. The model dialkyl D-glucaramides all displayed a large vicinal proton coupling between the central backbone glucaryl hydrogens, indicating an essentially fixed anti conformational arrangement of these protons. The MM3 molecular mechanics program was then applied to calculate the corresponding low-energy conformations of the structurally simplest of these molecules, tetra-O-acetyl-N,N'-dimethyl-D-glucaramide (4). Given the large number of dihedral angles to be considered and the apparent rigidity of these molecules around the central carbons of the glucaryl backbone, a number of conformational approximations based upon model compounds were applied regarding the rotameric disposition of the pendant O-acetyl and terminal N-methyl groups. The calculated, and dominant, lowest energy conformer has a sickle structure very similar to the global minimum conformation previously calculated for unprotected d-glucaramide. The x-ray crystal structure data from 4 indicated an extended conformation in the solid state and gave solid-state torsion angle information that was comparable to that obtained computationally.

  DOI：

  10.1080/07328300601039310
• 作为产物：
  描述：

  正己胺 、 methyl D-glucarate 1,4-lactone 以 甲醇 为溶剂， 反应 1.0h， 以98.12%的产率得到N,N'-dihexyl-D-glucaramide
  参考文献：
  名称：

  MM3 Conformational Analysis and X‐ray Crystal Structure of 2,3,4,5‐Tetra‐O‐Acetyl‐N,N′‐Dimethyl‐D‐Glucaramide as a Conformational Model for the d‐Glucaryl Unit of Poly(Alkylene 2,3,4,5‐Tetra‐O‐Acetyl‐d‐Glucaramides)

  摘要：

  This report describes the MM3 conformational analysis and X-ray crystal structure of tetra-O-acetyl-N,N'-dimethyl-D-glucaramide as a conformational model for the D-glucaryl monomer unit of poly(alkylene tetra-O-acyl-glucaramides). The driving force for this study was to determine the conformational preferences for the diacid unit as a function of the increasing steric bulk of pendant O-acyl groups: acetyl, propanoyl, 2-methylpropanoyl, and 2,2-dimethylpropanoyl. The model dialkyl D-glucaramides all displayed a large vicinal proton coupling between the central backbone glucaryl hydrogens, indicating an essentially fixed anti conformational arrangement of these protons. The MM3 molecular mechanics program was then applied to calculate the corresponding low-energy conformations of the structurally simplest of these molecules, tetra-O-acetyl-N,N'-dimethyl-D-glucaramide (4). Given the large number of dihedral angles to be considered and the apparent rigidity of these molecules around the central carbons of the glucaryl backbone, a number of conformational approximations based upon model compounds were applied regarding the rotameric disposition of the pendant O-acetyl and terminal N-methyl groups. The calculated, and dominant, lowest energy conformer has a sickle structure very similar to the global minimum conformation previously calculated for unprotected d-glucaramide. The x-ray crystal structure data from 4 indicated an extended conformation in the solid state and gave solid-state torsion angle information that was comparable to that obtained computationally.

  DOI：

  10.1080/07328300601039310

文献信息

• US5478374A
  申请人：——

  公开号：US5478374A

  公开（公告）日：1995-12-26