1-tridecylimidazole | 18994-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-tridecylimidazole
• 英文别名: 1-tridecyl-1H-imidazole；1-Tridecyl-1H-imidazole
• CAS: 18994-74-6
• 化学式: C₁₆H₃₀N₂
• 分子量: 250.428
• InChiKey: BBCHAGTYLQSTCK-UHFFFAOYSA-N

物化性质

• 沸点：
  378.9±11.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-tridecylimidazole 在 氢溴酸 作用下， 以 乙醚 为溶剂， 以78%的产率得到1-tridecylimidazolium bromide
  参考文献：
  名称：

  On the Mesophase Formation of 1,3-Dialkylimidazolium Ionic Liquids

  摘要：

  A series of seven different 1,3-dialkylimidazolium-based ion-pair salts with the same molecular weight and size but different symmetries was synthesized. For all salts, bromide was chosen as the counterion, giving the series ([CnIMCm][Br]), where IM = imidazolium and Cn and Cm are varying N-alkyl substituents with n + m = 13. Thus, the effect of symmetry on the physicochemical properties, such as thermal transitions, densities and viscosities and particularly mesophase formation, is investigated herein. All salts are fully characterized by NMR spectroscopy and mass spectrometry, and their physicochemical properties such as thermal transitions, densities, and viscosities are reported. Single crystal X-ray structure analysis is reported for 1-tridecylimidazolium bromide ([C0IMC13][Br]) and 1-ethyl-3-undecylimidazolium bromide ([C2IMC11][Br]). Salts 1-tridecylimidazolium bromide ([C0IMC13][Br]) and 1-dodecyl-3-methylimidazolium bromide ([C1IMC12][Br]) exhibit thermotropic liquid crystal behavior, confirmed by differential scanning calorimetry, polarized optical microscopy, and small-angle X-ray diffraction to be the SmA mesophase. A structure with interdigitation of alkyl chains is observed for all of [C0IMC13][Br], [C1IMC12][Br], and [C2IMC11][Br], despite the absence of thermotropic liquid crystalline behavior for the latter (and all other isomers with an alkyl chain length less than 12 carbon atoms). This allows us to draw the conclusion that for the liquid crystal phase of an ionic liquid to exist, not only are the calamitic shape and integral length of a molecule important but a minimal alkyl chain length of n = 12 is also required. Therefore, a dodecyl group could be considered as the functional group responsible for liquid crystalline behavior.

  DOI：

  10.1021/cg4004593
• 作为产物：
  描述：

  咪唑 、 1-溴十三烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以85%的产率得到1-tridecylimidazole
  参考文献：
  名称：

  On the Mesophase Formation of 1,3-Dialkylimidazolium Ionic Liquids

  摘要：

  A series of seven different 1,3-dialkylimidazolium-based ion-pair salts with the same molecular weight and size but different symmetries was synthesized. For all salts, bromide was chosen as the counterion, giving the series ([CnIMCm][Br]), where IM = imidazolium and Cn and Cm are varying N-alkyl substituents with n + m = 13. Thus, the effect of symmetry on the physicochemical properties, such as thermal transitions, densities and viscosities and particularly mesophase formation, is investigated herein. All salts are fully characterized by NMR spectroscopy and mass spectrometry, and their physicochemical properties such as thermal transitions, densities, and viscosities are reported. Single crystal X-ray structure analysis is reported for 1-tridecylimidazolium bromide ([C0IMC13][Br]) and 1-ethyl-3-undecylimidazolium bromide ([C2IMC11][Br]). Salts 1-tridecylimidazolium bromide ([C0IMC13][Br]) and 1-dodecyl-3-methylimidazolium bromide ([C1IMC12][Br]) exhibit thermotropic liquid crystal behavior, confirmed by differential scanning calorimetry, polarized optical microscopy, and small-angle X-ray diffraction to be the SmA mesophase. A structure with interdigitation of alkyl chains is observed for all of [C0IMC13][Br], [C1IMC12][Br], and [C2IMC11][Br], despite the absence of thermotropic liquid crystalline behavior for the latter (and all other isomers with an alkyl chain length less than 12 carbon atoms). This allows us to draw the conclusion that for the liquid crystal phase of an ionic liquid to exist, not only are the calamitic shape and integral length of a molecule important but a minimal alkyl chain length of n = 12 is also required. Therefore, a dodecyl group could be considered as the functional group responsible for liquid crystalline behavior.

  DOI：

  10.1021/cg4004593

文献信息

• Synthesis of N-Alkylated derivatives of imidazole as antibacterial agents
  作者：S. Khabnadideh、Z. Rezaei、A. Khalafi-Nezhad、R. Bahrinajafi、R. Mohamadi、A.A. Farrokhroz

  DOI：10.1016/s0960-894x(03)00591-2

  日期：2003.9

  N-Alkylation of imidazole, 2-methylimidazole and 2-methyl-4-nitroimidazole have been carried out to achieve effective antibacterial agents. The products were then investigated for antibacterial activity against Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa. Antibacterial effects of 1-alkylimidazole derivatives increase as the number of carbons in alkyl chain increases up to nine carbons. Also substitution of 2-methyl and 2-methyl-4-nitro groups on imidazole ring increases the antibacterial activity. (C) 2003 Elsevier Ltd. All rights reserved.
• Chemo-Immunotherapeutic Antimalarials Targeting Isoprenoid Biosynthesis
  作者：Yonghui Zhang、Wei Zhu、Yi-Liang Liu、Hong Wang、Ke Wang、Kai Li、Joo Hwan No、Lawrence Ayong、Anmol Gulati、Ran Pang、Lucio Freitas-Junior、Craig T. Morita、Eric Oldfield

  DOI：10.1021/ml4000436

  日期：2013.4.11

  We synthesized 30 lipophilic bisphosphonates and tested them in malaria parasite killing (targeting parasite geranylgeranyl diphosphate synthase, GGPPS) and human gamma delta T cell activation (targeting human farnesyl diphosphate synthase, FPPS). Similar patterns of activity were seen in inhibiting human FPPS and Plasmodium GGPPS, with short to medium chain-length species having most activity. In cells, shorter chain-length species had low activity, due to poor membrane permeability, and longer chain length species were poor enzyme inhibitors. Optimal activity was thus seen with similar to C-10 side-chains, which have the best combination of enzyme inhibition and cell penetration. We also solved the crystal structure of one potent inhibitor, bound to FPPS. The results are of interest since they suggest the possibility of a combined chemo/immuno-therapeutic approach to antimalarial development in which both direct parasite killing and gamma delta T cell activation can be achieved with a single compound.
• Synthèse et propriétés antibactériennes et antifongiques d'une série de 1-alkylimidazoles
  作者：A de Savignac、C Roques、M Hinedi、G Michel、A Lattes

  DOI：10.1016/0223-5234(90)90009-r

  日期：1990.6
• Metal Oxide Dispersion, Metal Oxide Electrode Film, and Dye Sensitized Solar Cell
  申请人：Kayama Susumu

  公开号：US20090014062A1

  公开（公告）日：2009-01-15

  A metal oxide dispersion comprising metal oxide particles with a necking structure, and a solvent, wherein the liquid droplet contact angle of the metal oxide dispersion to an ITO film (Indium-Tin Oxide type film) formed is from 0 to 60°. A metal oxide dispersion for the production of a dye-sensitized solar cell electrode, comprising Metal Oxide Particle Group F having a necking structure formed by m connected particles, Metal Oxide Particle Group G having only 0.2 m or less connected particles, and a solvent, and being formable into a film at 200° C. or less. A metal oxide electrode comprising an electrically conducting substrate having thereon a metal oxide layer comprising metal oxide particles bound by a binder, wherein the binder content is from 0.005 to 5 mass % based on the metal oxide film and the metal oxide layer has a pencil scratch strength of H or more according to JIS5600.
• [EN] IMPROVED METAL-LIGAND COMPLEX CATALYZED PROCESSES<br/>[FR] PROCEDES AMELIORES A CATALYSE PAR COMPLEXE METAL-LIGAND
  申请人：UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY CORPORATION

  公开号：WO1997020798A1

  公开（公告）日：1997-06-12

  (EN) This invention relates to a method of stabilizing a metal-organopolyphosphite ligand complex catalyst against deactivation in a process which comprises reacting one or more reactants in the presence of a metal-organopolyphosphite ligand complex catalyst and optionally free organopolyphosphite ligand to produce a reaction product fluid comprising one or more products, which method comprises conducting said process in the presence of one or more free heterocyclic nitrogen compounds sufficient to prevent and/or lessen deactivation of the metal-organopolyphosphite ligand complex catalyst.(FR) Procédé de stabilisation d'un catalyseur constitué d'un complexe métal-ligand organopolyphosphite pour empêcher sa désactivation dans un procédé consistant à faire réagir un ou plusieurs réactifs en présence d'un catalyseur constitué d'un complexe métal-ligand organopolyphosphite et d'un ligand organopolyphosphite éventuellement libre de façon à obtenir un fluide produit par une réaction constitué d'un ou de plusieurs produits. Le procédé consiste à effectuer cette opération en présence d'un ou plusieurs composés d'azote hétérocycliques, en quantité suffisante pour prévenir et/ou diminuer la désactivation du catalyseur constitué d'un complexe métal-ligand organopolyphosphite.