(S)-2-(dodecyloxy)-1-methyl-2-oxoethylammonium 4-toluenesulfonate | 135424-88-3

• 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: (S)-2-(dodecyloxy)-1-methyl-2-oxoethylammonium 4-toluenesulfonate
• 英文别名: L-alanine dodecyl ester p-toluenesulfonate；(S)-1-(dodecyloxy)-1-oxopropan-2-aminium p-toluenesulfonate；dodecyl (2S)-2-aminopropanoate;4-methylbenzenesulfonic acid
• CAS: 135424-88-3
• 化学式: C₇H₈O₃S*C₁₅H₃₁NO₂
• 分子量: 429.621
• InChiKey: UXEFAGLBDTXGOA-UQKRIMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  106.69
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(dodecyloxy)-1-methyl-2-oxoethylammonium 4-toluenesulfonate 、 N-(S)-1-carboxyethyl-3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide 在 咪唑 、 盐酸 作用下， 反应 1.5h， 以66%的产率得到N-(S)-1-carboxyethyl-N'-(S)-2-dodecyloxy-1-methyl-2-oxoethyl-3,4,9,10-perylenetetracarboxyldiimide
  参考文献：
  名称：

  Facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides involving α-amino acids

  摘要：

  A facile synthesis of chiral unsymmetric perylene tetracarboxylic diimides (PDIs) has been developed and the first two nonracemic chiral amphiphilic PDIs have been synthesized. The key building blocks, AB bifunctional 3,4,9, 10-perylenetetracarboxylic-3,4-anhydride-9, 10-imides, were prepared conveniently from enantiomerically pure alpha-amino acids, which were introduced as the steric and stereochemical controlling units. Such building blocks allow the incorporation of sterically and stereochemically controlled PDI moieties into both terminal and inner positions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.099
• 作为产物：
  描述：

  L-丙氨酸 、 十二烷醇 、 对甲苯磺酸 以 甲苯 为溶剂， 以60%的产率得到(S)-2-(dodecyloxy)-1-methyl-2-oxoethylammonium 4-toluenesulfonate
  参考文献：
  名称：

  Stable supramolecular helical structure of C6-symmetric hydrogen-bonded hexakis(phenylethynyl)benzene derivatives with amino acid pendant groups and their unique fluorescence properties

  摘要：

  通过新型 C6 对称氢键盘状分子--带有手性丙氨酸部分的六(苯乙炔基)苯衍生物--的自组装，形成了高度稳定的超分子螺旋结构，并呈现出具有较大斯托克斯位移的橙色准分子发射。

  DOI：

  10.1039/b803532f

文献信息

• Efficient Microwave-Assisted Synthesis of Ionic Esterified Amino Acids
  作者：Ricardo Cerón-Camacho、Jorge Aburto、Luisa E. Montiel、Eugenio A. Flores、Frisia Cuellar、Rafael Martínez-Palou

  DOI：10.3390/molecules16108733

  日期：——

  In this work, an efficient microwave-assisted methodology for the esterification of unprotected α-amino acids is described. Ionic esterified amino acids were synthesized in satisfactory yields in a facile one-pot solventless protocol from unprotected amino acids and alcohols under acid catalysis (MsOH or p-TsOH) to afford the pure products after a simple work-up procedure. This procedure can also be extended to the preparation of long and short chain alkyl and benzyl esters.

  本研究描述了一种高效的微波辅助方法来酯化未受保护的α-氨基酸。在酸催化（MsOH 或 p-TsOH）条件下，以未保护的氨基酸和醇为原料，通过简便的单锅无溶剂方案合成了离子酯化氨基酸，产率令人满意。该方法还可用于制备长链和短链烷基酯和苄基酯。
• Gel-solution phase transition of organogels with photoreversibility: l-amino acid organogelators with azobenzene
  作者：Masahiro Suzuki、Yukari Maruyama、Kenji Hanabusa

  DOI：10.1016/j.tetlet.2016.06.111

  日期：2016.8

  Simple organogelators with organic salt structures by mixing of l-amino acid dodecyl esters and azobenzene-4-caroboxylic acid, were synthesized and their organogelation properties were examined. These gelators formed organogels in many organic fluids. The acetonitrile gels showed a reversibly photochemical phase transition; they changed into the solution under ultraviolet light (365 nm), and then it

  通过混合1-氨基酸十二烷基酯和偶氮苯-4-caroboxylic acid合成具有有机盐结构的简单有机胶凝剂，并研究了它们的有机胶凝性能。这些胶凝剂在许多有机流体中形成有机凝胶。乙腈凝胶显示出可逆的光化学相变；他们在紫外线（365 nm）下变成溶液，然后通过可见光（450 nm）重整。凝胶至溶液的相变取决于1-氨基酸的化学结构。这种依赖性是由偶氮苯部分的聚集模式的差异引起的。
• Development of furan-2,5-dicarboxylic acid (FDCA)-based organogelators
  作者：Dorian Rabaud、Paul Dussart、Guylaine Ducouret、Pierre-Antoine Albouy、Jérémy Forté、Benjamin Isare、Laurent Bouteiller

  DOI：10.1039/d3sm00771e

  日期：——

  Organogels are used in a wide range of applications for which the development of new bio-based organogelators is highly desirable. While furan-2,5-dicarboxylic acid (FDCA) is a promising molecule for the synthesis of bio-based polyesters, it has never been used in the context of organogels. This study explores the possibility to design FDCA-based organogelators that self-assemble into fibrillar networks

  有机凝胶具有广泛的应用，因此非常需要开发新型生物基有机凝胶剂。虽然呋喃-2,5-二甲酸 (FDCA) 是一种很有前景的生物基聚酯合成分子，但它从未用于有机凝胶。本研究探讨了设计基于 FDCA 的有机凝胶剂的可能性，该凝胶剂可自组装成通过氢键稳定的纤维网络。凝胶测试表明该凝胶剂系列具有多种凝胶液体（尤其是非极性液体）的多功能性。通过 FTIR 和 CD 光谱、晶体学、粉末 X 射线衍射和流变学研究了凝胶的结构。
• Molecular Assembly and Gelating Behavior of (<scp>l</scp>)‐Alanine Derivatives
  作者：Takahiro Soeta、Shota Kurobe、Yutaro Nirei、Naoto Kurokawa、Weilin Wei、Ayhan Yurtsever、Takeshi Fukuma、Yutaka Ukaji

  DOI：10.1002/chem.202300455

  日期：2023.7.11

  A low-molecular-weight organogelator derived from (L)-amino acids was designed and synthesized. The (L)-alanine derivatives were determined to be excellent gelators, forming good gels even when smaller amounts were added. Self-molecular aggregates were observed to be helical or sheet-like, and the gels were constructed by forming aggregates by self-molecular recognition.

  设计并合成了一种源自(L)-氨基酸的低分子量有机凝胶剂。(L)-丙氨酸衍生物被确定为优异的胶凝剂，即使添加量较少也能形成良好的凝胶。观察到自分子聚集体呈螺旋状或片状，通过自分子识别形成聚集体来构建凝胶。