N,N'-dimethyl-D-glucaramide | 156016-05-6

• 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'-dimethyl-D-glucaramide
• 英文别名: Dimethyl D-glucaramide；D-glucaric acid bis-methylamide；D-Glucarsaeure-bis-methylamid；(2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-N,N'-dimethylhexanediamide
• CAS: 156016-05-6
• 化学式: C₈H₁₆N₂O₆
• 分子量: 236.225
• InChiKey: AMXUWQVGWZSGSC-OMMKOOBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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'-dimethyl-D-glucaramide 、 乙酸酐 在 吡啶 作用下， 以50.07%的产率得到2,3,4,5-tetra-O-acetyl-N,N'-dimethyl-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：

  糖质酸-1,4-内酯 在 氢氧化钾 、 甲基亚硝基脲 作用下， 以 甲醇 、 乙醚 、 水 、 丙酮 为溶剂， 反应 2.17h， 生成 N,N'-dimethyl-D-glucaramide
  参考文献：
  名称：

  Chen, Liang; Kiely, Donald E., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 4, p. 585 - 602

  摘要：

  DOI：

文献信息

• MM3(96) CONFORMATIONAL ANALYSIS OF <scp>d</scp>-GLUCARAMIDE AND X-RAY CRYSTAL STRUCTURES OF THREE <scp>d</scp>-GLUCARIC ACID DERIVATIVES—MODELS FOR SYNTHETIC POLY(ALKYLENE <scp>d</scp>-GLUCARAMIDES)
  作者：Susan D. Styron、Alfred D. French、Joyce D. Friedrich、Charles H. Lake、Donald E. Kiely

  DOI：10.1081/car-120003736

  日期：2002.5.31

  An exhaustive conformational analysis Of D-glucaramide was carried out using MM3(96) [MM3(96). Molecular Mechanics Software used with permission from N.L. Allinger; University of Georgia]. Nine torsion angles were each driven in increments of 120degrees, generating 19,683 starting conformations. Each conformation was then fully energy-minimized using MM3's block diagonal/full matrix optimization option at dielectric constants of both 3.5 and 6.5. Conformer populations were calculated based on the modeling results and calculated theoretical average H-1 vicinal coupling constants were compared to experimental values obtained in D2O solution. Crystal structures of three acyclic D-glucaric acid derivatives (N,N'-dimethyl-D-glucaramide, dipotassium D-glucarate, and sodium potassium D-glucarate) are reported. These structures and that of previously reported monopotassiurn olucarate correspond closely with model conformations that were within one kcal/mol of the global minimum.
• Kurtz; Wilson, Journal of Biological Chemistry, 1939, vol. 129, p. 695
  作者：Kurtz、Wilson

  DOI：——

  日期：——