1-hexadecyl-4-(4-pyridyl)pyridinium bromide | 76842-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-hexadecyl-4-(4-pyridyl)pyridinium bromide
• 英文别名: 4-(N-hexadecylpyridinium-4-yl)pyridine bromide；N-(n-hexadecyl)-4-(4'-pyridyl)pyridinium bromide；4-(4'-pyridyl)-1-hexadecyl-pyridinium bromide；1-hexadecyl-4,4'-bipyridinium bromide；1-hexadecyl-4,4'-dipyridinium bromide；1-Hexadecyl-4-pyridin-4-ylpyridin-1-ium;bromide
• CAS: 76842-00-7
• 化学式: Br*C₂₆H₄₁N₂
• 分子量: 461.529
• InChiKey: YMIBWDLXTPQMGH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  16.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-hexadecyl-4-(4-pyridyl)pyridinium bromide 以 甲醇 、 硝基甲烷 为溶剂， 反应 84.0h， 生成 DASP-(12-V-16)
  参考文献：
  名称：

  Synthesis and Characterization of Donor−Acceptor Chromophores for Unidirectional Electron Transfer

  摘要：

  A series of electron-transfer chromophores containing a donor and acceptor linked by an alkyl spacer were synthesized, and their electronic spectra were investigated. By inclusion with amylose, the supramolecularly encapsulated chromophores exhibit enhanced fluorescence quenching with discrete distance dependence and acquire the ability to sustain self-assemblies of a densely packed supramolecular array on a SiOH/Si substrate.

  DOI：

  10.1021/ol063000y
• 作为产物：
  描述：

  4,4'-联吡啶 、 溴代十六烷 生成 1-hexadecyl-4-(4-pyridyl)pyridinium bromide
  参考文献：
  名称：

  自组装两亲性紫精系统的新颖性质。1.胶束系统中电子交换反应的研究

  摘要：

  DOI：

  10.1021/j150606a001

文献信息

• New Photogeneration System of Dihydronicotinamide and Viologen Radical Using Ru(bpy)₃²⁺
  作者：Masahiro Suzuki、Mutsumi Kimura、Kenji Hanabusa、Hirofusa Shirai

  DOI：10.1246/cl.1999.337

  日期：1999.4

  Visible light irradiation (λ > 440 nm) on a methanol solution containing Ru(bpy)32+ and nicotinamide covalently bound to viologen produces both dihydronicotinamide and viologen radical.

  可见光照射（λ>440 nm）在含有Ru(bpy)32+和烟酰胺的甲醇溶液中，与紫精共价结合，产生二氢烟酰胺和紫精自由基。
• The antibacterial activity of 4,4′-bipyridinium amphiphiles with conventional, bicephalic and gemini architectures
  作者：Melissa C. Grenier、Robert W. Davis、Kelsey L. Wilson-Henjum、Jade E. LaDow、Jacob W. Black、Kevin L. Caran、Kyle Seifert、Kevin P.C. Minbiole

  DOI：10.1016/j.bmcl.2012.04.079

  日期：2012.6

  Dialkyl 4,4'-bipyridinium compounds are widely employed for their useful redox properties, and are commonly known as viologens due to their intense coloration upon reduction. Despite their prevalence and amphiphilic nature, the antibacterial activity of these compounds remains largely unreported. We have thus prepared a series of mono-and bis-alkylated analogs of 4,4'-bipyridine to investigate structure-activity relationships in their inhibition of a battery of Gram positive and Gram negative bacteria. The prepared cationic compounds were conventional (one cationic head, one non-polar tail), bicephalic (two heads, one tail), or gemini (two heads, two tails) in their amphiphilic structure. Additionally, an isomeric series of six bis-alkylated compounds ranging from symmetric (PQ-11,11) to highly asymmetric (PQ-20,2) were prepared. Four themes of bioactivity emerged: (1) the most bioactive compounds were gemini in structure; (2) 22 carbons in the alkyl chains, with little to modest asymmetry, led to optimal activity; (3) bicephalic compounds were generally comparable to conventional amphiphiles, though only about 12 carbons in the alkyl chains were solubilized in water by each cationic nitrogen; (4) the effects of counterion identity were not evident between chlorides and bromides; however, the presence of the iodide counterion inhibited dissolution in all compounds tested. Three isomeric compounds with little to no asymmetry in tail length, PQ-11,11, PQ-12,10, and PQ-14,8, prepared as the bromide salts, showed comparable and highly potent activity, with MIC levels around 2 mu M against 3 of 4 bacteria tested. The simple (one-to two-step) syntheses of potent antimicrobials portend well for future optimization. (C) 2012 Elsevier Ltd. All rights reserved.
• Mechanisms of transmembrane electron transfer: diffusion of uncharged redox forms of viologen, 4,4'-bipyridine, and nicotinamide with long alkyl chains
  作者：Leif Hammarstroem、Mats Almgren、Johan Lind、Gabor Merenyi、Thomas Norrby、Bjoern Aakermark

  DOI：10.1021/j100141a031

  日期：1993.9

  Transmembrane electron transfer in lecithin (phosphatidylcholine) vesicles was studied by pulse radiolysis. Upon reduction, cetylmethylviologen (N-hexadecyl-N'-methyl-4,4'-bipyridinium CMV), cetylbipyridine (4-(N-hexadecylpyridinium-4-yl)pyridine, CB), and cetylnicotinamide (N-hexadecyl-3-(aminocarbonyl)pyridinium, CNA) transferred electrons from the bulk water phase to Fe(CN)63- in the internal water phase of the vesicles. The transmembrane electron transfer was found in all cases to proceed through diffusion of uncharged forms of the redox mediators (CMV0, CB0, and CNA0, respectively) but the kinetic behavior varied considerably. The mechanisms for CB and CNA were simple, the reaction following first-order kinetics, and the transmembrane diffusion was rate limiting (k = (1.5 +/- 0.3) x 10(3) S-1 for CB and k = 3.2 +/- 0.5 s-1 for CNA). The mechanism for CMV was more complicated, and the reaction followed second-order kinetics. The rate-determining step was proposed to be the disproportionation of two viologen radicals formed by the radiation pulse (2CMV+ double-line arrow pointing left and right CMV0 + CMV2+), followed by rapid transmembrane diffusion of CMVO and its subsequent reoxidation by Fe(CN)63-. In pulse radiolysis, and in phosphorescence quenching experiments with Pt2(P2O5)4H84-, CB0 and CB+ were used as models in order to obtain the rates of transmembrane diffusion of CMV0 and CMV+, respectively. Our results exclude the possibility of electron tunneling between viologens on opposite sides of the membrane, and they provide strong arguments against transmembrane diffusion of viologen radical (CMV+).
• Redox active functionally polymerized surfactant vesicles. Syntheses and characterization
  作者：Pietro Tundo、Donald J. Kippenberger、Mario J. Politi、Patricia Klahn、Janos H. Fendler

  DOI：10.1021/ja00384a018

  日期：1982.10
• Novel properties of the self-assembling amphipathic viologen system. 1. A study of electron-exchange reactions in micellar systems
  作者：K. Takuma、T. Sakamoto、T. Nagamura、T. Matsuo

  DOI：10.1021/j150606a001

  日期：1981.3