N-辛基-D-谷氨酰胺 | 18375-61-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: N-辛基-D-谷氨酰胺
• 中文别名: N-辛基-D-葡萄酰胺
• 英文名称: N-n-octyl-D-gluconamide
• 英文别名: N-(1-octyl)-D-gluconamide；n-octyl-D-gluconamide；(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxy-N-octylhexanamide
• CAS: 18375-61-6
• 化学式: C₁₄H₂₉NO₆
• 分子量: 307.387
• InChiKey: KTMBZDQOFPBYBL-FVCCEPFGSA-N

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

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  N-辛基-D-谷氨酰胺 在 吡啶 作用下， 以 氯仿 为溶剂， 25.0~50.0 ℃ 、1500.0 MPa 条件下， 反应 65.0h， 生成 6-deoxy-6-(1-imidazolyl)-N-(octyl)-D-gluconamide tetraacetate
  参考文献：
  名称：

  Organogels from Carbohydrate Amphiphiles

  摘要：

  Gluconamides can be easily functionalized to give a variety of compounds that form organogels with a high viscosity. N-n-octyl-D-gluconamide-6-benzoate gelates a large variety of organic solvents, including 1,2-xylene, chloroform, ethyl acetate, and ethanol, to form gels which are, in some cases, stable even above the boiling point of the pure solvent; The 2-methoxy, 6-imidazolyl, 6-acetyl, and 6-cyclohexanoyl derivatives also show gelation, but the 2,4;3,5-dimethylene-protected derivatives do not. Detailed H-1 NMR, TR, and X-ray powder diffraction studies reveal that the molecules of most gelators are packed in a head-to-tail fashion. If there is, however, the possibility to form interlayer hydrogen bonds, as in the case of N-n-octyl-D-gluconamide or N-n-octyl-D-gluconamide-6-(3-pyridyl carboxylate), the molecules are packed head-to-head. Some gluconamides, e.g., those with aliphatic substituents, express their molecular chirality in the supramolecular structures, whereas others, in particular those containing a large aromatic substituent on carbon atom C-6, yield nonchiral aggregates, probably due to interfering pi-pi stacking interactions of the substituents. DSC experiments show that the formation of the gels is an entropy-driven process.

  DOI：

  10.1021/jo981158t
• 作为产物：
  描述：

  辛胺 、 葡糖酸 以 甲醇 为溶剂， 反应 4.0h， 生成 N-辛基-D-谷氨酰胺
  参考文献：
  名称：

  Baeyens-Volant, D.; Fornasier, R.; Szalai, E., Molecular Crystals and Liquid Crystals (1969-1991), 1986, vol. 135, p. 93 - 110

  摘要：

  DOI：

文献信息

• Synthesis and interfacial properties of new 6-sulfate sugar-based anionic surfactants
  作者：Bemba Abdellahi、Rémy Bois、Sema Golonu、Gwladys Pourceau、David Lesur、Vincent Chagnault、Audrey Drelich、Isabelle Pezron、Alla Nesterenko、Anne Wadouachi

  DOI：10.1016/j.tetlet.2021.153113

  日期：2021.6

  chain. Twelve of the as-synthesized anionic glycolipids, including nine novel sulfated compounds, were investigated for their surface activity at the air/liquid interface and for their self-assembling properties. These sugar-based surfactants show surface properties similar to those of commercial anionic surfactants (SDS and SLES) with good ability to reduce surface tension. The obtained results confirm

  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。
• Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes
  作者：Rudi J. H. Hafkamp、Bas P. A. Kokke、Iris M. Danke、Hubertus P. M. Geurts、Alan E. Rowan、Martinus C. Feiters、Roeland J. M. Nolte

  DOI：10.1039/a608266a

  日期：——

  Functionalized gluconamides and their metal complexes are shown to give supramolecular assemblies, in some cases chiral, and to form organogels in a large variety of organic solvents, e.g. methacrylate mixtures which can be polymerized, as well as o-xylene, chloroform, ethyl acetate, ethanol and tetrahydrofuran.

  研究表明，功能化葡糖酰胺及其金属络合物可形成超分子组装体，在某些情况下具有手性，并可在多种有机溶剂中形成有机凝胶，例如可聚合的甲基丙烯酸酯混合物，以及邻二甲苯、氯仿、乙酸乙酯、乙醇和四氢呋喃。
• The chiral bilayer effect stabilizes micellar fibers
  作者：Juergen Hinrich Fuhrhop、Peter Schnieder、Joerg Rosenberg、Egbert Boekema

  DOI：10.1021/ja00245a032

  日期：1987.5

  Dihelical fibers several micrometers in length and gels were obtained by spontaneous aggregation of octyl L- and D-gluconamides. The single strands have the thickness of a bimolecular layer. No fibers are formed from the racemate. The tendency of the chiral amphiphiles to aggregate to very long fibers instead of three-dimensional crystals is rationalized with a “chiral bilayer effect”. This effect is caused

  通过辛基L-和D-葡糖酰胺的自发聚集获得几微米长的双螺旋纤维和凝胶。单链具有双分子层的厚度。外消旋体不形成纤维。手性两亲物聚集成非常长的纤维而不是三维晶体的趋势被“手性双层效应”合理化。这种效应是由从尾对尾疏水双层到晶体的重排缓慢引起的，其中分子片以头对尾的方式排列。还报告了表明老化凝胶中缓慢重排的热谱图。
• Face specific surface properties of pharmaceutical crystals
  作者：Tim H. Muster、Clive A. Prestidge

  DOI：10.1002/jps.10125

  日期：2002.6

  adhesion properties have been shown to correlate strongly with the face specific surface chemistry. This, in turn, is controlled by the molecular arrangement at the specific crystal face, which has been characterized by time-of-flight secondary-ion mass spectrometry (ToF SIMS) and inferred from molecular models. Of specific note, the magnitude of the adhesion force between a crystal face and a hydrophobic

  各种表面特定技术已用于确定模型药物晶体的表面特定结构，化学性质和润湿性，即N，n-辛基-d-葡糖酰胺和磺胺噻唑（多晶型I和III）。通过使用胶体探针原子力显微镜（AFM）研究了单个晶体面的润湿特性以及与化学修饰的二氧化硅球的相互作用，研究了它们的表面能。接触角（动态和静态），相互作用力和粘附特性已显示出与面部特定表面化学性质密切相关。反过来，这又受特定晶面上分子排列的控制，这已通过飞行时间二次离子质谱（ToF SIMS）进行了表征，并可以从分子模型中推断出来。需要特别注意的是 晶体表面和疏水性胶体探针之间的粘附力的大小与表面特定的平衡接触角呈线性关系。这些研究进一步加深了我们对药用晶体表面特性的理解，并在考虑加工，配制和运输时具有一定的意义。
• Spectral insights into gelation microdynamics of N-octyl-D-gluconamide in water
  作者：Shengtong Sun、Peiyi Wu

  DOI：10.1039/c1sm05548h

  日期：——

  tail to the chiral carbohydrate head followed by the final immobilization of the solvent, which meanwhile, is actually a continuous dehydration process from the hydrophobic core to the outer hydrophilic chiral head. The driving force of the gelation process in microdynamics can only be the dehydration process of hydrophobic octyl chains, but with final helical superstructures being stabilized by amide-associated

  近红外光谱结合二维相关光谱法（2Dcos）和微扰相关移动窗（PCMW）技术来说明水凝胶器的凝胶化微观动力学机理 N-辛基-D-葡糖酰胺（8-GA），当从球形胶束冷却后，可迅速自团聚成螺旋双层胶束纤维。Boltzmann拟合和PCMW可以轻松确定胶凝温度大约为。72°C，转变温度范围为70–75°C。此外，可以观察到CH相关的泛音出现谱带移动和分裂现象，表明由辛基尾巴形成了许多有序且紧密的疏水核。另一方面，使用2Dcos识别胶凝过程中的顺序，得出的结论是，所有的基团运动都从辛基尾部连续转移到手性碳水化合物头上，然后最终固定了溶剂，这是实际上是从疏水核到外部亲水性手性头的连续脱水过程。微观动力学中凝胶化过程的驱动力只能是疏水性辛基链的脱水过程，