n-dodecyldimethylferrocenylmethylammonium bromide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: n-dodecyldimethylferrocenylmethylammonium bromide
• 英文别名: (ferrocenylmethyl)dodecyldimethylammonium bromide；(Ferrocenylmethyl)dodecyldimethylammoniumBromide
• 化学式: Br*C₂₅H₄₂FeN
• 分子量: 492.366
• InChiKey: NCFVAYLOZTVJBB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,N-dimethylaminomethylferrocene 、 溴代十二烷 以 乙腈 为溶剂， 反应 72.0h， 以73.4%的产率得到n-dodecyldimethylferrocenylmethylammonium bromide
  参考文献：
  名称：

  茂金属QAC：将二茂铁部分结合到monoQAC和bisQAC结构中

  摘要：

  受到将茂金属官能团结合到各种生物活性结构，特别是抗菌肽中的启发，我们努力通过结合二茂铁部分来拓宽季铵化合物 (QAC) 的结构多样性。因此，以高产率制备了 23 种含二茂铁的单 QAC 和双 QAC，并测试了其对多种细菌的活性，包括革兰氏阴性菌株和一组临床分离的 MRSA 菌株。二茂铁 QAC 被证明是有效的防腐剂，其中一些对所有测试的细菌显示出个位数的微摩尔活性，这表明在扩展防腐 QAC 的结构多样性方面又迈出了一步。

  DOI：

  10.1002/cmdc.202000605

文献信息

• Metallocene QACs: The Incorporation of Ferrocene Moieties into monoQAC and bisQAC Structures
  作者：Kyle J. Sommers、Brian S. Bentley、Robert G. Carden、Savannah J. Post、Ryan A. Allen、Renee C. Kontos、Jacob W. Black、William M. Wuest、Kevin P. C. Minbiole

  DOI：10.1002/cmdc.202000605

  日期：2021.2.4

  ammonium compounds (QACs) by the incorporation of the ferrocene moiety. Accordingly, 23 ferrocene‐containing mono‐ and bisQACs were prepared in high yields and tested for activity against a variety of bacteria, including Gram‐negative strains and a panel of clinically isolated MRSA strains. Ferrocene QACs were shown to be effective antiseptics with some displaying single‐digit micromolar activity against

  受到将茂金属官能团结合到各种生物活性结构，特别是抗菌肽中的启发，我们努力通过结合二茂铁部分来拓宽季铵化合物 (QAC) 的结构多样性。因此，以高产率制备了 23 种含二茂铁的单 QAC 和双 QAC，并测试了其对多种细菌的活性，包括革兰氏阴性菌株和一组临床分离的 MRSA 菌株。二茂铁 QAC 被证明是有效的防腐剂，其中一些对所有测试的细菌显示出个位数的微摩尔活性，这表明在扩展防腐 QAC 的结构多样性方面又迈出了一步。
• Reversible formation and disruption of micelles by control of the redox state of the head group
  作者：T. Saji、K. Hoshino、S. Aoyagui

  DOI：10.1021/ja00310a020

  日期：1985.11

  Etudes electrochimiques et spectroscopiques dans le cas du bromure de (ferrocenyl-methyl) dodecyl dimethylammonium

  Etudeselectrochimiques et spectroscopiques dans le cas du bromure de（二茂铁甲基）十二烷基二甲基铵
• Adsorption-Desorption Dynamics of Amphiphilic Ferrocenes on Electrodes Studied by Flow Voltammetry
  作者：Wenfeng Peng、Deling Zhou、James F. Rusling

  DOI：10.1021/j100018a035

  日期：1995.5

  Adsorption-desorption kinetics and equilibria were measured by using flow voltammetry. The principle involves flowing an adsorbate-free blank electrolyte solution past a working electrode and switching the flow to a solution of adsorbate, or beginning with the adsorbate solution and switching to the blank. Changes in surface concentration of adsorbate with time are monitored by fast cyclic voltammetry. Mathematical models assuming the Langmuir isotherm were developed for adsorption-desorption kinetics under hydrodynamic conditions and employed for nonlinear regression of peak current versus time data to obtain adsorption parameters. Alkylammonium surfactants having ferrocene (Fc) attached to cationic head groups and alkyl chain lengths from C8 to C16 were investigated. Results suggest that these adsorbates achieve monolayer coverage from submicromolar solutions under flow conditions. Adsorption rates are controlled by both intrinsic adsorption kinetics and diffusion rates, Residence times on the electrode were 14s for Fc-C8 and Fc-C12 and 66s for Fc-C16. Free energies of adsorption (Delta G(ads)(o) ) increased with the length of the hydrocarbon chain by about 0.75 kJ mol(-1) per CH2 group, in accord with a hydrophobic component to the driving force. Delta G(ads)(o) depended weakly on electrode potential.
• Pankratov, V. A.; Kucherova, N. L.; Abramzon, A. A., Journal of applied chemistry of the USSR, 1988, vol. 61, p. 300 - 303
  作者：Pankratov, V. A.、Kucherova, N. L.、Abramzon, A. A.

  DOI：——

  日期：——
• Charge Density Overcomes Steric Hindrance of Ferrocene Surfactant in Switchable Oil‐in‐Dispersion Emulsions
  作者：Yunshan Liu、Haojie Zhang、Wanqing Zhang、Bernard P. Binks、Zhenggang Cui、Jianzhong Jiang

  DOI：10.1002/anie.202210050

  日期：2023.1.26

  oil-in-dispersion emulsions in combination with positively charged alumina nanoparticles. Not only can reversible formation/destabilization of oil-in-dispersion emulsions be achieved by redox reactions, but also reversible transformation between oil-in-dispersion emulsions and Pickering emulsions can be achieved by pH trigger.

  双头二茂铁表面活性剂 (Fc + N + C 12 ) 可以与带正电荷的氧化铝纳米粒子结合稳定可切换的分散油包乳液。不仅可以通过氧化还原反应实现分散油包油乳液的可逆形成/失稳，而且可以通过pH触发实现分散油包油乳液和皮克林乳液之间的可逆转化。