2-(Dimethylamino)ethyl-hexadecyl-dimethylazanium;bromide | 14866-59-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(Dimethylamino)ethyl-hexadecyl-dimethylazanium;bromide
• 英文别名: 2-(dimethylamino)ethyl-hexadecyl-dimethylazanium;bromide
• CAS: 14866-59-2
• 化学式: Br*C₂₂H₄₉N₂
• 分子量: 421.548
• InChiKey: HGDOCVNHNFXRFW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(Dimethylamino)ethyl-hexadecyl-dimethylazanium;bromide 、 溴代十二烷 以 乙腈 为溶剂， 反应 20.0h， 以77%的产率得到
  参考文献：
  名称：

  [EN] BISCATIONIC AND TRISCATIONIC AMPHILES AS ANTIMICROBIAL AGENTS
  [FR] COMPOSÉS AMPHIPHILES BISCATIONIQUES ET TRISCATIONIQUES UTILISÉS COMME AGENTS ANTIMICROBIENS

  摘要：

  本公开提供了一种抗微生物组合物，包括一种双阳离子或三阳离子两性分子，以及制备此类抗微生物组合物的方法，以及使用此类化合物或组合物进行抗微生物用途的方法。抗微生物组合物可以包括具有以下结构式(I)的化合物，其中R是未取代或可选择取代的亚甲基基团，s是在1到6范围内的整数，R1、R2、R3或R4是H或未取代或可选择取代的C1-4烷基，X是卤素，m和n是在5到25范围内的整数，且m不等于n。或者，抗微生物组合物可以包括具有以下结构式(III)或(IV)的化合物，其中R1、R2、R3、R4、R5或R6是H或未取代或可选择取代的C1-4烷基，X或Y是卤素，m和n是在5到25范围内的整数。

  公开号：

  WO2015069760A1
• 作为产物：
  描述：

  四甲基乙二胺 、 溴代十六烷 以 丙酮 为溶剂， 反应 3.0h， 以97%的产率得到2-(Dimethylamino)ethyl-hexadecyl-dimethylazanium;bromide
  参考文献：
  名称：

  [EN] BISCATIONIC AND TRISCATIONIC AMPHILES AS ANTIMICROBIAL AGENTS
  [FR] COMPOSÉS AMPHIPHILES BISCATIONIQUES ET TRISCATIONIQUES UTILISÉS COMME AGENTS ANTIMICROBIENS

  摘要：

  本公开提供了一种抗微生物组合物，包括一种双阳离子或三阳离子两性分子，以及制备此类抗微生物组合物的方法，以及使用此类化合物或组合物进行抗微生物用途的方法。抗微生物组合物可以包括具有以下结构式(I)的化合物，其中R是未取代或可选择取代的亚甲基基团，s是在1到6范围内的整数，R1、R2、R3或R4是H或未取代或可选择取代的C1-4烷基，X是卤素，m和n是在5到25范围内的整数，且m不等于n。或者，抗微生物组合物可以包括具有以下结构式(III)或(IV)的化合物，其中R1、R2、R3、R4、R5或R6是H或未取代或可选择取代的C1-4烷基，X或Y是卤素，m和n是在5到25范围内的整数。

  公开号：

  WO2015069760A1

文献信息

• [EN] BISCATIONIC AND TRISCATIONIC AMPHILES AS ANTIMICROBIAL AGENTS<br/>[FR] COMPOSÉS AMPHIPHILES BISCATIONIQUES ET TRISCATIONIQUES UTILISÉS COMME AGENTS ANTIMICROBIENS
  申请人：UNIV TEMPLE

  公开号：WO2015069760A1

  公开（公告）日：2015-05-14

  The present disclosure provides an antimicrobial composition including a compound which is a biscationic or triscationic amphiphile, and the method of making such an antimicrobial composition, and the method of using such a compound or composition for antimicrobial use. The antimicrobial composition can include a compound having the formula (I) wherein R is a methylene group unsubstituted or optionally substituted, s is an integer in the range from 1 to 6, R1, R2, R3 or R4 is H or a C 1-4 alkyl unsubstituted or optionally substituted, X is a halogen, m and n are integers in the range from 5 to 25, and m is not equal to n. Alternatively, the antimicrobial composition can comprise a compound having the formula (III) or (IV) wherein R1, R2, R3, R4 R5, or R6 is H or a C1-4 alkyl unsubstituted or optionally substituted, X or Y is a halogen, and m and n are integers in the range from 5 to 25.

  本公开提供了一种抗微生物组合物，包括一种双阳离子或三阳离子两性分子，以及制备此类抗微生物组合物的方法，以及使用此类化合物或组合物进行抗微生物用途的方法。抗微生物组合物可以包括具有以下结构式(I)的化合物，其中R是未取代或可选择取代的亚甲基基团，s是在1到6范围内的整数，R1、R2、R3或R4是H或未取代或可选择取代的C1-4烷基，X是卤素，m和n是在5到25范围内的整数，且m不等于n。或者，抗微生物组合物可以包括具有以下结构式(III)或(IV)的化合物，其中R1、R2、R3、R4、R5或R6是H或未取代或可选择取代的C1-4烷基，X或Y是卤素，m和n是在5到25范围内的整数。
• Effects of Structure Dissymmetry on Aggregation Behaviors of Quaternary Ammonium Gemini Surfactants in a Protic Ionic Liquid EAN
  作者：Xudong Wang、Qintang Li、Xiao Chen、Zhihong Li

  DOI：10.1021/la304004u

  日期：2012.12.4

  The aggregation behaviors of a series of dissymmetric cationic Gemini surfactants, [CmH2m+1(CH3)(2)N(CH2)(2)N(CH3)(2)CnH2n+1]Br-2, designated as m-2-n (with a fixed m + n = 24, m = 16, 14, 12) have been investigated in a protic ionic liquid, ethylammonium nitrate (EAN). Surface tension, polarized optical microscopy (POM), small-angle X-ray scattering (SAXS), and rheological measurements are adopted to investigate the micellization and lyotropic liquid crystal (LLC) formation. The obtained results indicate that the structure dissymmetry plays an important role in aggregation process of m-2-n. With increasing degree of dissymmetry, the critical micellization concentration, the maximum reduction of solvent surface tension, and the minimum area occupied per surfactant molecule at the air/EAN interface all become smaller. The thermostability of formed LLCs is therefore improved because of the more compact molecules. These characteristics can be explained by the enhancement of solvophobic effect due to the increased structure dissymmetry of Gemini surfactants.
• TMEDA-derived biscationic amphiphiles: An economical preparation of potent antibacterial agents
  作者：Jacob W. Black、Megan C. Jennings、Julianne Azarewicz、Thomas J. Paniak、Melissa C. Grenier、William M. Wuest、Kevin P.C. Minbiole

  DOI：10.1016/j.bmcl.2013.11.070

  日期：2014.1

  Bis-alkylated derivatives of N,N,N',N'-tetramethylethylenediamine (TMEDA) represent a well-known class of versatile biscationic amphiphiles, owing to their low cost and ease of preparation. Asymmetric TMEDA derivatives, however, have been studied significantly less, particularly in regards to their antimicrobial properties. We have thus prepared a series of 36 mono-and bis-alkylated TMEDA derivatives to evaluate their inhibition of bacterial growth. This series of compounds showed low micromolar activity against a panel of four bacteria. Optimal inhibition was observed when the biscationic amphiphiles possessed modest asymmetry and were composed of between 20 and 24 total carbon atoms in the side chains. These amphiphiles were prepared in a simple two-step procedure, utilizing inexpensive materials and atom-economical reactions, making them practical for further development. (C) 2013 Elsevier Ltd. All rights reserved.