N-hexadecylglucosamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-hexadecylglucosamine
• 英文别名: (2R,3R,4S,5S,6R)-2-(hexadecylamino)-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol；(2R,3R,4S,5S,6R)-2-(hexadecylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₂H₄₅NO₅
• 分子量: 403.603
• InChiKey: SYUBNBITHGKZMU-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-hexadecylglucosamine 、 草酸 以81%的产率得到
  参考文献：
  名称：

  SANDKUEHLER, P.;LEHMANN, R.;HASE, C.

  摘要：

  DOI：
• 作为产物：
  描述：

  可得然胶 、 十六胺 以 甲醇 为溶剂， 以72%的产率得到N-hexadecylglucosamine
  参考文献：
  名称：

  Influence of the Variation of the Alkyl Chain Length ofN-Alkyl-β-d-glycosylamine Derivatives on Antifungal Properties

  摘要：

  Twelve new glucosidic and galactosidic derivatives of N-alkylaminosugars with different alkylamines from 6 to 18 carbons were synthesized and characterized by H-1 and C-13 NMR. Their antifungal activity against the food fungal pathogen Aspergillus niger was evaluated using the radial growth assay. The influence of the variation of the alkyl chain length of N-alkylaminosugars on the mycelium growth was then discussed. Inhibition by the different alkylamines is shown as a biostatic effect rather than a biocidal effect. It was observed that alkylamines keep their antifungal properties after a thermal treatment compatible with food packaging and processing.

  DOI：

  10.1021/jf3015798

文献信息

• A designed bi-functional sugar-based surfactant: micellar catalysis for C–X coupling reaction in water
  作者：Xin Ge、Shihui Zhang、Xinzhi Chen、Xuemin Liu、Chao Qian

  DOI：10.1039/c9gc00964g

  日期：——

  A bi-functional sugar-based surfactant ALA14 was designed as the ligand and micelle constructor and demonstrated to promote the copper-catalyzed C–X coupling reaction in water. The nature of this micelle, formed by sugar-based surfactants, was investigated with CMC, DLS, and TEM, by which encapsulation and aggregation of the substrates in micelles were verified. Additionally, it was addressed by 1H-NMR

  一种双功能糖基表面活性剂ALA14被设计为配体和胶束构造剂，并被证明能促进水中铜的C-X偶联反应。用CMC，DLS和TEM研究了由糖基表面活性剂形成的胶束的性质，从而验证了胶束中底物的包封和聚集。另外，通过1 H-NMR分析发现底物的富集位置在亲脂性烷基链中。最后，在这项工作中获得了中等至极高的目标产品收率。这种非常简单的策略扩大了水中C–X偶联反应的范围。最值得注意的是，水和ALA14都可以回收再利用。
• The aggregation behaviour of two structurally isomeric glycolipids
  作者：George S. Attard、Wesley P. Blackaby、Andrew R. Leach

  DOI：10.1016/0009-3084(94)90114-7

  日期：1994.10

  The two structurally isomeric glycolipids N-octyl-(1-hexadecylamido)-beta-D-glucopyranoside (Glc-N-[8/16]) and N-hexadecyl-(1-octylamido)-beta-D-glucopyranoside (Glc-N[16/8]) were synthesized. The lyotropic phase behaviour of these isomers was investigated in order to determine the extent to which the relative disposition of the alkyl chains with respect to the amide unit affects the aggregation properties

  两个结构异构的糖脂N-辛基-（1-十六烷基酰胺基）-β-D-吡喃葡萄糖苷（Glc-N- [8/16]）和N-十六烷基-（1-辛基酰胺基）-β-D-吡喃葡萄糖苷（Glc-合成了N 16/8。为了确定烷基链相对于酰胺单元的相对位置影响两亲物的聚集性质的程度，研究了这些异构体的溶致相行为。两种异构体均显示出层状和逆拓扑立方中间相。相对于Glc-N- [16/8]异构体，非层状相的程度和多态性在Glc-N- [8/16]异构体中似乎更明显。为了使这种行为合理化，进行了分子力学研究。