2-octanoylamido-2-deoxy-β-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-octanoylamido-2-deoxy-β-D-glucopyranose
• 英文别名: Octanoyl B-D-glucosylamine；N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]octanamide
• 化学式: C₁₄H₂₇NO₆
• 分子量: 305.371
• InChiKey: DOPGJHMBFNGSTK-DKTYCGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-deoxy-2-amino glucose 、 辛酰氯 反应 3.0h， 生成 2-octanoylamido-2-deoxy-β-D-glucopyranose 、 2-octanoylamido-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  Sugar-based anionic surfactants: synthesis and micelle formation of sodium methyl 2-acylamido-2-deoxy-6-O-sulfo-d-glucopyranosides

  摘要：

  The following sequence of reactions has been employed to synthesize the title anionic surfactants:[GRAPHICS]where R=C7H15; C11H23; and C15H31, respectively, and Py refers to pyridine. Aggregation of the surfactants synthesized (predominantly alpha anomers) in water was studied at 40 degreesC by conductivity measurements. Increasing the chain length of R decreases the critical micelle concentration (CMC) and the degree of counter-ion dissociation. The dependence of the Gibbs free energy of micellization and CMC on the length of R is similar to other ionic surfactants, but the head-group, i.e., the sulfated sugar moiety is less hydrophilic than the structurally related group -(OCH2-CH2)(2)-OSO3-Na+, most probably because of intermolecular H-bonding in the micellar pseudo-phase (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00077-5

文献信息

• Sugar-based anionic surfactants: synthesis and micelle formation of sodium methyl 2-acylamido-2-deoxy-6-O-sulfo-d-glucopyranosides
  作者：Reinaldo C Bazito、Omar A El Seoud

  DOI：10.1016/s0008-6215(01)00077-5

  日期：2001.5

  The following sequence of reactions has been employed to synthesize the title anionic surfactants:[GRAPHICS]where R=C7H15; C11H23; and C15H31, respectively, and Py refers to pyridine. Aggregation of the surfactants synthesized (predominantly alpha anomers) in water was studied at 40 degreesC by conductivity measurements. Increasing the chain length of R decreases the critical micelle concentration (CMC) and the degree of counter-ion dissociation. The dependence of the Gibbs free energy of micellization and CMC on the length of R is similar to other ionic surfactants, but the head-group, i.e., the sulfated sugar moiety is less hydrophilic than the structurally related group -(OCH2-CH2)(2)-OSO3-Na+, most probably because of intermolecular H-bonding in the micellar pseudo-phase (C) 2001 Elsevier Science Ltd. All rights reserved.