N-cetyl-N-methylmorpholinium bromide | 13316-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-cetyl-N-methylmorpholinium bromide
• 英文别名: 4-Hexadecyl-4-methylmorpholin-4-ium bromide；4-hexadecyl-4-methylmorpholin-4-ium;bromide
• CAS: 13316-71-7
• 化学式: Br*C₂₁H₄₄NO
• 分子量: 406.49
• InChiKey: MDDMJLVYCDPTPQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基吗啉 、 溴代十六烷 以 甲苯 为溶剂， 反应 48.0h， 以79.3%的产率得到N-cetyl-N-methylmorpholinium bromide
  参考文献：
  名称：

  水溶液中表面活性剂N-烷基-N-甲基吗啉鎓溴化物的表面吸附和胶束形成

  摘要：

  本文研究了N-烷基-N-甲基吗啉溴化物（[Mor 1，n ] Br n = 12、14、16）在水溶液中的表面吸附和胶束形成。通过表面张力的测量，表面张力降低的（Π有效性CMC），最大表面过量浓度（Γ最大）和最小面积（A分钟）每个表面活性剂分子所占据在空气/水界面，在25℃下可以推导出。此外，临界胶束浓度（CMC）和各种热力学参数（标准Gibbs能（ΔG米0），焓（Δħ米0），和熵（Δ小号米0））是在不同温度下通过电导率测量得出的。热力学参数的结果表明，胶束化过程是由熵驱动的。

  DOI：

  10.1016/j.molliq.2016.04.112
• 作为试剂：
  描述：

  O-p-nitrophenyl O-n-hexyl chloromethylphosphonate 在 水 、 N-cetyl-N-methylmorpholinium bromide 、 sodium hydroxide 作用下， 生成 4-nitrophenol sodium salt 、 chloromethyl(hexoxy)phosphinic acid
  参考文献：
  名称：

  Supramolecular Catalytic Systems Based on a Cationic Amphiphile and Sodium Polystyrene Sulfonate for Decomposition of Organophosphorus Pollutants

  摘要：

  A supramolecular catalytic system for hydrolytic decomposition of toxic phosphorus acid esters has been obtained on the basis of a cationic surfactant with a morpholinium head group and sodium polystyrene sulfonate. Self-organization of the new binary catalytic system has been studied by tensiometry, conductometry, pH-metry, spectrophotometry, and dynamic and electrophoretic light scattering, and its aggregation thresholds have been determined. High solubilizing ability of the system with respect to a hydrophobic guest has been revealed. The morpholinium surfactant has been found to accelerate the hydrolysis of phosphonates up to 50 times in comparison to the reaction in water. The apparent hydrolysis rate constant in the presence of the polyelectrolyte decreases threefold due to reduction of the reactant binding constants.

  DOI：

  10.1134/s1070428019010032

文献信息

• Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: Effect of phosphate group and environment of the ammonium cation on their biological activity
  作者：Miloš Lukáč、Ján Mojžiš、Gabriela Mojžišová、Martin Mrva、František Ondriska、Jindra Valentová、Ivan Lacko、Marián Bukovský、Ferdinand Devínsky、Janka Karlovská

  DOI：10.1016/j.ejmech.2009.08.011

  日期：2009.12

  dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimethylammonium bromide have been synthesized. The prepared compounds exhibit significant cytotoxic, antifungal and antiprotozoal activities. Alkylphosphocholines possess higher antifungal activity against Candida albicans in comparison with quaternary ammonium compounds. However, quaternary ammonium compounds exhibit

  已经合成了十六烷基磷胆碱和十六烷基三甲基溴化铵的一系列二烷基氨基和氮杂环类似物。制备的化合物显示出显着的细胞毒性，抗真菌和抗原生动物活性。与季铵化合物相比，烷基磷酸胆碱对白色念珠菌具有更高的抗真菌活性。然而，与烷基磷酸胆碱相比，季铵化合物对人肿瘤细胞和卢氏棘阿米巴具有显着更高的活性。另外，已经研究了它们的溶血毒性。讨论了被测化合物的结构与生物学活性之间的关系。
• Polyfunctional supramolecular systems based on surfactants containing the hydroxyalkyl moiety in the head group
  作者：E. I. Yackevich、A. B. Mirgorodskaya、S. S. Lukashenko、L. Ya. Zakharova

  DOI：10.1007/s11172-014-0669-5

  日期：2014.8

  hydroxyethyl moiety in the head group were determined using a complex of physicochemical methods. The aggregation behavior of these compounds was found to vary insignificantly, whereas the catalytic effect of the hydroxyethyl derivative on the hydrolysis of carboxylic acid esters more than an order of magnitude exceeds the effect of the non-functionalized surfactant. One of the reasons for this phenomenon

  N-十六烷基-N-甲基吗啉溴化物及其类似物的胶束水溶液中的临界胶束浓度、表面电位和抗衡离子的结合程度使用物理化学方法的复合物来确定。发现这些化合物的聚集行为变化不大，而羟乙基衍生物对羧酸酯水解的催化作用超过非官能化表面活性剂的作用一个数量级以上。这种现象的原因之一可能是荧光光谱检测到的化学反应区的微极性增加。
• Self-organization and lipoplex formation of cationic surfactants with morpholinium head group
  作者：A.B. Mirgorodskaya、E.I. Yackevich、D.R. Gabdrakhmanov、S.S. Lukashenko、Yu.F. Zuev、L.Ya. Zakharova

  DOI：10.1016/j.molliq.2016.05.010

  日期：2016.8

  increases and the aggregation number decreases upon the transition from a monocationic to a gemini analog. Morpholinium surfactants demonstrate a much higher solubilizing capacity toward the hydrophobic probe Orange OT as compared to the typical trimethylammonium surfactant. Both morpholinium surfactants form lipoplexes with a DNA decamer, which is strongly supported by the ethidium bromide exclusion

  合成了具有吗啉鎓头基和十六烷基尾巴的新型两性表面活性剂（MP 16-6-16）。已经评估了两亲物的自组装性质，并将其与它们的单阳离子对应物（MP-16）和三甲基铵类似物进行了比较。与MP-16相比，双子蛋白的临界胶束浓度（0.01 mM）较低，而与常规双子蛋白16-6-16相比则略低。结果表明，当胶束表面电势从单阳离子向双生子类似物过渡时，其胶束表面电势增加而聚集数减少。与典型的三甲基铵表面活性剂相比，吗啉表面活性剂对疏水探针Orange OT的溶解能力要高得多。两种吗啉鎓表面活性剂都与DNA十聚体形成脂复合物，溴化乙锭排除试验和电荷中和数据有力地支持了这一点。高增溶和络合活性以及与脂质双层结合的能力使我们推荐吗啉鎓表面活性剂作为药物和基因载体的候选物。
• Quaternary Ammonium Salts as Germicides. III. Quaternary Ammonium Salts Derived from Cyclic Amines
  作者：R. S. Shelton、M. G. van Campen、C. H. Tilford、H. C. Lang、L. Nisonger、F. J. Bandelin、H. L. Rubenkoenig

  DOI：10.1021/ja01209a014

  日期：1946.5
• Investigation of Novel Triple-Responsive Wormlike Micelles
  作者：Mingwei Zhao、Mingwei Gao、Caili Dai、Chenwei Zou、Zhe Yang、Xuepeng Wu、Yifei Liu、Yining Wu、Sisi Fang、Wenjiao Lv

  DOI：10.1021/acs.langmuir.7b01011

  日期：2017.5.2

  Smart wormlike micelles with stimuli-tunable rheological properties may be useful in a variety of applications, such as in molecular devices and sensors. The formation of triplestimuli-responsive systems so far has been a challenging and important issue. In this work, a novel triplestimuli (photo-, pH-, and thermoresponsive) wormlike micelle is constructed with N-cetyl-N-methylmorpholinium bromide and trans-cinnamic acid (CA). The corresponding multiresponsive behaviors of wormlike micellar system were revealed using cryogenic transmission electron microscopy, a rheometer, and H-1 NMR. The rheological properties of wormlike micellar system under different temperatures, pH conditions, and UV irradiation times are measured. As confirmed by H-1 NMR, chemical structure of a CA molecule can be altered by the multiple stimulation from an exotic environment. We expect it to be a good model for triple-responsive wormlike micelles, which is helpful to understand the mechanism of triple-responsiveness and widen their applications.