11-trimethylammonium-1-undecene bromide | 123349-44-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 11-trimethylammonium-1-undecene bromide
• 英文别名: N,N,N-trimethylundec-10-en-1-ammonium bromide；N,N,N-trimethylundec-10-enamonnium bromide；N,N,N-Trimethylundec-10-en-1-aminium bromide；trimethyl(undec-10-enyl)azanium;bromide
• CAS: 123349-44-0
• 化学式: Br*C₁₄H₃₀N
• 分子量: 292.303
• InChiKey: IIOQHMGYTCXYRH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-trimethylammonium-1-undecene bromide 在 硫代乙酸 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以85%的产率得到N,N,N-trimethyl-(11-mercaptaundecyl)ammonium chloride
  参考文献：
  名称：

  Preparation and antimicrobial behaviour of quaternary ammonium thiol derivatives able to be grafted on metal surfaces

  摘要：

  New thiol derivatives containing a quaternary ammonium group bearing variable hydrocarbon chains via an amide connector or not between the sulphur and nitrogen atoms were synthesised with the future aim to be grafted on metal surfaces for obtaining contact-active auto-bactericidal surfaces. Their biostatic and bactericidal activities were evaluated against four microbial strains (Pseudomonas aeruginosa, Staphylococcus aureus, Aspergillus niger and Candida albicans). The presence of the thiol and amide functions in these surfactants was discussed in relation with the antimicrobial activity along with the influence of the length of alkyl chains in order to determine which molecular parameters are 'critical' for biological activity, and consequently what molecules must be chosen for grafting on metal surface. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.05.007
• 作为产物：
  描述：

  11-溴-1-十一烯 、 三甲胺 以 乙醇 为溶剂， 以86%的产率得到11-trimethylammonium-1-undecene bromide
  参考文献：
  名称：

  Hybrid nanoreceptors for high sensitivity detection of small molecules by NMR chemosensing

  摘要：

  自组装的金纳米颗粒在胶体二氧化硅纳米颗粒上表现出更高的磁化转移效率，在NMR化学传感实验中可以检测到低至10μM的分析物。

  DOI：

  10.1039/d0cc07559k

文献信息

• Influence of the Spatial Distribution of Cationic Functional Groups at Nanoparticle Surfaces on Bacterial Viability and Membrane Interactions
  作者：Yongqian Zhang、Natalie V. Hudson-Smith、Seth D. Frand、Meghan S. Cahill、Larissa S. Davis、Z. Vivian Feng、Christy L. Haynes、Robert J. Hamers

  DOI：10.1021/jacs.0c02737

  日期：2020.6.17

  While positively charged nanomaterials induce cytotoxicity in many organisms, much less is known about how the spatial distribution and presentation of molecular surface charge impact nanoparticle-biological interactions. We systematically functionalized diamond nanoparticle surfaces with five different cationic surface molecules having different molecular structures and conformations, including four small ligands and one polymer, and we then probed the molecular-level interaction between these nanoparticles and bacterial cells. Shewanella oneidensis MR-1 was used as a model bacterial cell system to investigate how the molecular length and conformation of cationic surface charges influence their interactions with the Gram-negative bacterial membranes. Nuclear magnetic resonance (NMR) and X-ray photoelectron spectroscopy (XPS) demonstrate the covalent modification of the nanoparticle surface with the desired cationic organic monolayers. Surprisingly, bacterial growth-based viability (GBV) and membrane damage assays both show only minimal biological impact by the NPs functionalized with short cationic ligands within the concentration range tested, yet NPs covalently linked to a cationic polymer induce strong cytotoxicity, including reduced cellular viability and significant membrane damage at the same concentration of cationic groups. Transmission electron microscopy (TEM) images of these NP-exposed bacterial cells show that NPs functionalized with cationic polymers induce significant membrane distortion and the production of outer membrane vesicle-like features, while NPs bearing short cationic ligands only exhibit weak membrane association. Our results demonstrate that the spatial distribution of molecular charge plays a key role in controlling the interaction of cationic nanoparticles with bacterial cell membranes and the subsequent biological impact. Nanoparticles functionalized with ligands having different lengths and conformations can have large differences in interactions even while having nearly identical zeta potentials. While the zeta potential is a convenient and commonly used measure of nanoparticle charge, it does not capture essential differences in molecular-level nanoparticle properties that control their biological impact.
• Kaschierklebemassen mit Barriereeigenschaften gegenüber Gasen und Dämpfen
  申请人：Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.

  公开号：EP1217052B1

  公开（公告）日：2005-10-26
• Preparation and antimicrobial behaviour of quaternary ammonium thiol derivatives able to be grafted on metal surfaces
  作者：Pascal Thebault、Elisabeth Taffin de Givenchy、Richard Levy、Yves Vandenberghe、Frédéric Guittard、Serge Géribaldi

  DOI：10.1016/j.ejmech.2008.05.007

  日期：2009.2

  New thiol derivatives containing a quaternary ammonium group bearing variable hydrocarbon chains via an amide connector or not between the sulphur and nitrogen atoms were synthesised with the future aim to be grafted on metal surfaces for obtaining contact-active auto-bactericidal surfaces. Their biostatic and bactericidal activities were evaluated against four microbial strains (Pseudomonas aeruginosa, Staphylococcus aureus, Aspergillus niger and Candida albicans). The presence of the thiol and amide functions in these surfactants was discussed in relation with the antimicrobial activity along with the influence of the length of alkyl chains in order to determine which molecular parameters are 'critical' for biological activity, and consequently what molecules must be chosen for grafting on metal surface. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Hybrid nanoreceptors for high sensitivity detection of small molecules by NMR chemosensing
  作者：Federico De Biasi、Daniele Rosa-Gastaldo、Fabrizio Mancin、Federico Rastrelli

  DOI：10.1039/d0cc07559k

  日期：——

  Self-assembled gold nanoparticles onto colloidal silica nanoparticles exhibited higher magnetization transfer efficiencies in NMR chemosensing experiments, allowing the detection of analytes as low as 10 μM.

  自组装的金纳米颗粒在胶体二氧化硅纳米颗粒上表现出更高的磁化转移效率，在NMR化学传感实验中可以检测到低至10μM的分析物。