sodium 2-(1-decyloxycarbonyl-2S-phenyl-ethylcarbamoyl)-benzene sulfonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: sodium 2-(1-decyloxycarbonyl-2S-phenyl-ethylcarbamoyl)-benzene sulfonate
• 英文别名: sodium;N-[(2S)-1-decoxy-1-oxo-3-phenylpropan-2-yl]-2-sulfobenzenecarboximidate
• 化学式: C₂₆H₃₄NO₆S*Na
• 分子量: 511.615
• InChiKey: SZBSKFMSUARPFZ-BQAIUKQQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  癸醇 在 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 sodium 2-(1-decyloxycarbonyl-2S-phenyl-ethylcarbamoyl)-benzene sulfonate
  参考文献：
  名称：

  New amino acid-based anionic surfactants and their use as enantiodiscriminating lyotropic liquid crystalline NMR solvents

  摘要：

  New amino acid-based anionic surfactants have been synthesized and their use as chiral oriented NMR solvents studied. A series of sulfonated amphiphilic L-Phe or L-Ala derivatives with pentyl to tetradecyl tails were prepared by reacting the corresponding amino acid esters with o-sulfobenzoic anhydride. Their critical micelle concentrations (CMCs) range from 1.6 x 10(-5) to 1.4 x 10(-2) mol/L and depend on the alkyl chain length as well as on the nature of the amino acid block. These values are comparatively lower than those of classical surfactants such as alkylbenzenesulfonates and N-acylamino-acid carboxylates. Their use as chiral liquid crystals (CLC) for analytical purposes is reported. In particular, it is shown that aqueous solutions of these chiral sulfonates in the presence of chlorinated solvents (CHCl3, CH2Cl2, C2H2Cl4, or CCl4) provide homogeneous oriented NMR solvents able to differentiate between enantiomers of D,L-alanine-2-d(1) using proton and deuterium NMR spectroscopy. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.022

文献信息

• New amino acid-based anionic surfactants and their use as enantiodiscriminating lyotropic liquid crystalline NMR solvents
  作者：Krystyna Baczko、Chantal Larpent、Philippe Lesot

  DOI：10.1016/j.tetasy.2004.01.022

  日期：2004.3

  New amino acid-based anionic surfactants have been synthesized and their use as chiral oriented NMR solvents studied. A series of sulfonated amphiphilic L-Phe or L-Ala derivatives with pentyl to tetradecyl tails were prepared by reacting the corresponding amino acid esters with o-sulfobenzoic anhydride. Their critical micelle concentrations (CMCs) range from 1.6 x 10(-5) to 1.4 x 10(-2) mol/L and depend on the alkyl chain length as well as on the nature of the amino acid block. These values are comparatively lower than those of classical surfactants such as alkylbenzenesulfonates and N-acylamino-acid carboxylates. Their use as chiral liquid crystals (CLC) for analytical purposes is reported. In particular, it is shown that aqueous solutions of these chiral sulfonates in the presence of chlorinated solvents (CHCl3, CH2Cl2, C2H2Cl4, or CCl4) provide homogeneous oriented NMR solvents able to differentiate between enantiomers of D,L-alanine-2-d(1) using proton and deuterium NMR spectroscopy. (C) 2004 Elsevier Ltd. All rights reserved.