N-十二烷基-2-羟基苯甲酰胺 | 10586-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-十二烷基-2-羟基苯甲酰胺
• 英文名称: N-dodecyl-2-hydroxybenzamide
• CAS: 10586-70-6
• 化学式: C₁₉H₃₁NO₂
• 分子量: 305.461
• InChiKey: ZETBIRNOTNNZCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-acetoxy-benzoic acid dodecylamide 在 sodium hydroxide 作用下， 生成 N-十二烷基-2-羟基苯甲酰胺
  参考文献：
  名称：

  Formation of domain structure of erythrocyte membrane in Wistar rat fed with CeCl3 per os

  摘要：

  To explore the possibility of absorption of lanthanides via digestive duct and their effects on the membrane structure and permeability of erythrocytes, the fine structure of erythrocyte membrane from Wistar rats, fed for 70 days of daily administration per os with 20 mg CeCl3/kg weight, was imaged by means of atomic force microscopy and FT-IR deconvolution spectra. The results show that, although the erythrocytes maintain the intact shape, the change of secondary structure, aggregation and crosslinking of the protein particles of membrane surface and the enlarged lipid regions lead to the domain structure formation. This structure might be responsible for the increasing permeability of erythrocyte membrane.

  DOI：

  10.1007/bf02884943

文献信息

• Fast synthesis of amides from ethyl salicylate under microwave radiation in a solvent-free system
  作者：Rafaely N. Lima、Valdenizia R. Silva、Luciano de S. Santos、Daniel P. Bezerra、Milena B. P. Soares、André L. M. Porto

  DOI：10.1039/c7ra11434f

  日期：——

  The reaction employing CAL-B also permitted a moderate conversion for the production of amides S-Ae-Aj (3–42%). However, in our efforts to reduce the amide synthesis time (24 h), the reactions were performed in the presence of microwave-MW radiation using a free-solvent system [60 °C, PBA (15 mol%) or WC], which reduced the time of the reaction by 32-fold (45 min) and afforded nine amides (S-Aa-Ah and

  在这项研究中，酰胺键的形成是有机化学中最重要的反应之一，使用水杨酸乙酯和十种不同的伯胺对其进行了评估。在最优化的实验条件下，即60°C，己烷，苯基硼酸-PBA（15 mol％），硼酸-BA（15 mol％）或不使用催化剂-WC的条件下，使用加热板放置24 h，可获得酰胺具有出色的孤立产量（WC，占S-Aa-Ad的77-94％； PBA，占S-Ae-Aj的11-94％；以及BA，占S-Ae-Aj的28-90％）。使用CAL-B的反应还允许适度转化生成酰胺S-Ae-Aj（3–42％）。但是，在我们减少酰胺合成时间（24小时）的努力中，反应是在微波-微波辐射存在下使用自由溶剂系统[60°C，PBA（15摩尔％）或WC]进行的，将反应时间减少了32倍（45分钟），得到了9种酰胺（S-Aa-Ah和S-Aj），分离产率为80-99％，S-Ai的产率为23％。细胞毒性分析表明，酰胺S-银是能够与IC抑制
• Salicylsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP0262587A2

  公开（公告）日：1988-04-06

  Die Erfindung betrifft als neue Substanzen N-Octyl­salicylsäureamid und N-Decyl-salicylsäureamid, ein Verfahren zur Herstellung der genannten Verbindungen aus Salicylsäuremethylester und einem primären Amin sowie die Verwendung der Amide in antimikrobiell wir­kenden Zusammensetzungen.

  本发明涉及的新物质包括 N-辛基水杨酸酰胺和 N-癸基水杨酸酰胺、从水杨酸甲酯和伯胺制备上述化合物的工艺以及这些酰胺在抗菌剂组合物中的用途。
• The Salol Reaction
  作者：James A. VanAllan

  DOI：10.1021/ja01203a509

  日期：1947.11
• Aminolysis of linoleic and salicylic acid derivatives with Candida antarctica lipase B: A solvent-free process to obtain amphiphilic amides for cosmetic application
  作者：Ana Maria Mouad、Delphine Taupin、Laurent Lehr、Florent Yvergnaux、André Luiz Meleiro Porto

  DOI：10.1016/j.molcatb.2016.01.002

  日期：2016.4

  In this biotechnological process, the fatty amides (9Z,12Z)-N-dodecyloctadeca-9,12-dienamide (3) and N-dodecy1-2-hydroxybenzamide (5), respectively derived from linoleic acid and salicylic acid were synthesized through aminolysis reactions catalyzed by Candida antarctica lipase B. These amphiphilic compounds receive great attention from cosmetic industry due to a range of beneficial properties for skin. The aminolysis reactions were performed with the esters ethyl linoleate (1) and ethyl salicylate (4) as acyl group donors and the fatty compound N-dodecylamine (2) as the nucleophilic substrate. The aminolysis reactions were carried out in a solvent-free process, which is beneficial from an environmental and economical perspective, at 65 degrees C and reduced pressure (50 mbar). Parameters as enzyme amount and substrates molar ratios were investigated and the products were monitored by HPLC analysis. The conversion rates were measured through disappearance of ethyl linoleate and ethyl salicylate. The best conversion rates (up to 95%) were obtained by adding an enzyme amount of 5.0 g/mol of acyl donor group substrate and an equimolar substrates ratio (1:1). The products characterization was performed by High Resolution Mass Spectrometry, Infrared spectroscopy and Nuclear Magnetic Ressonance. This work reveals that enzymatic synthesis provides an attractive way for the cosmetic industrial production of fatty amides, which may represent key ingredients to maintain and/or restore a healthy skin. (C) 2016 Elsevier B.V. All rights reserved.