N-dodecyl D-galactonamide

• 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-dodecyl D-galactonamide
• 英文别名: (2R,3S,4S,5R)-N-dodecyl-2,3,4,5,6-pentahydroxyhexanamide
• 化学式: C₁₈H₃₇NO₆
• 分子量: 363.495
• InChiKey: WUTZOLDBWJNAMI-LTIDMASMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  130
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-dodecyl D-galactonamide 在 吡啶 、 三氧化硫吡啶 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 7.0h， 以42%的产率得到sodium N-dodecyl D-galactonamide 6-sulfate
  参考文献：
  名称：

  新型6-硫酸盐糖基阴离子表面活性剂的合成及界面性质

  摘要：

  合成了三族在单糖的主要位置上带有硫酸盐官能团的阴离子糖基表面活性剂，并比较了它们的理化性质。第一家庭对应于市售的八- 6-硫酸衍生物和十二烷基β- d -葡糖- 和吡喃半乳糖苷。第二个和第三个家族在硫酸化单糖（半乳糖、葡萄糖或木糖）和疏水性烷基链之间包含一个酰胺接头。研究了 12 种合成的阴离子糖脂（包括 9 种新型硫酸化化合物）在空气/液体界面的表面活性和自组装性能。这些糖基表面活性剂的表面特性与商业阴离子表面活性剂（SDS 和 SLES）相似，具有良好的降低表面张力的能力。获得的结果证实了人们对这些新的生物基分子在各种配方中潜在替代阴离子表面活性剂的兴趣。

  DOI：

  10.1016/j.tetlet.2021.153113
• 作为产物：
  描述：

  十二烷基伯胺 、 D-半乳糖酸-1,4-内酯 以 甲醇 为溶剂， 生成 N-dodecyl D-galactonamide
  参考文献：
  名称：

  Supramolecular Assemblies of Diacetylenic Aldonamides

  摘要：

  The study of novel amphiphiles that form nonspheroidal assemblies upon hydration is fundamental to understanding the relationship between molecular structure and supramolecular morphology. Structural components of previously reported amphiphiles were used to design the single chain diacetylenic aldonamides reported here. Open chain sugar headgroups were linked via an amide bond to a hydrophobic tail. Diacetylenes were incorporated in the alkyl chain both as a structural component and as a reactive unit. Photopolymerization was used to test the molecular ordering of the hydrophobic region of the assemblies and to enhance their thermal and chemical stability. The electron density of the diacetylenes allowed direct imaging of the assemblies by TEM. The morphology and reactivity of a series of N-dodeca-5,7-diynylaldonamides were determined. The aldonamides were derived from two aldoheptoses, D-glycero-D-gluconamide and D-glycero-L-mannonamide; four aldohexoses, D-galactonamide, D-gluconamide, L-mannonamide, and D-gulonomide; two aldopentoses, L-arbanonamide and L-lyxonamide; and two aldotetroses, L-threonamide and D-erythronamide. N-Dodecylaldonamide analogues were prepared and examined to evaluate the importance of the diacetylene group on the morphology. The microscopy and molecular modeling data indicate that at least two packing arrangements for these assemblies are possible. One is the head-to-head bilayer packing typical of most amphiphilic molecules; the other is a head-to-tail arrangement. The head-to-head packing results in assemblies which are planar, helical, or tubular. The head-to-tail packing arrangement and ''dromic'' hydrogen-bonding patterns are associated with fiber-like supramolecular assemblies. Numerous potential applications of tubule microstructures have been proposed. The relative ease of preparation of many of these aldonamide molecules and their assemblies recommends them for many of these applications.

  DOI：

  10.1021/ja00101a026