N-dodecyl-4,13-diaza-18-crown-6 | 72535-47-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-dodecyl-4,13-diaza-18-crown-6
• 英文别名: 7-dodecyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 72535-47-8
• 化学式: C₂₄H₅₀N₂O₄
• 分子量: 430.672
• InChiKey: HCJWTOFLVUWAGC-UHFFFAOYSA-N

物化性质

• 沸点：
  539.1±45.0 °C(Predicted)
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.19
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-dodecyl-4,13-diaza-18-crown-6 在 sodium carbonate 作用下， 以 various solvent(s) 为溶剂， 反应 122.0h， 生成 N,N'-bis<12-(4'-dodecyl-4',13'-diaza-18-crown-6)-3,6,9-trioxaundec-1-yl>-4,13-diaza-18-crown-6
  参考文献：
  名称：

  Synthetic Models for Transmembrane Channels: Structural Variations That Alter Cation Flux

  摘要：

  Twelve novel bis- or tris(macrocyclic) compounds have been designed as models for cation-conducting channels that function in phospholipid bilayer vesicle membranes. In general, the channel model systems have the structure ''sidearm-crown-spacer-crown-spacer-crown-sidearm'', although certain features have been altered from compound to compound to assess the structure-activity relationship. Two additional compounds have been prepared exclusively as controls. The ionophores have been incorporated into the membranes either by warming the compound with the preformed vesicle or by incorporation during vesicle formation. The two methods gave identical results within experimental error. Cation flux was assessed by two different analytical methods. In one case, the fluorescent dye pyranine was encapsulated within vesicles containing ionophore. Proton transport was then monitored by changes in dye fluorescence with time following an acid pulse. Ionophoretic activity far most of the compounds was studied using a dynamic NMR method in which the flux rate of Na-23(+) through the bilayer was monitored. All NMR studies were done in conjunction with gramicidin as a control to minimize experimental variations from run to run. Several of the synthetic ionophores showed cation conduction of as much as 40% of the activity of gramicidin. Apparently, small structural changes significantly altered flux rates and two known carriers closely related to the channel formers failed to exhibit measurable transport under comparable conditions.

  DOI：

  10.1021/ja00134a011
• 作为产物：
  描述：

  在 氢气 、 钯 作用下， 反应 8.0h， 生成 N-dodecyl-4,13-diaza-18-crown-6
  参考文献：
  名称：

  Synthesis and characterization of an amphiphilic cobalt cage complex with aza-crown spacer

  摘要：

  The synthesis, spectrophotometric and surfactant properties of a novel amphiphilic cobalt cage metallosurfactant with an aza-oxa crown ether spacer and dodecyl hydrocarbon tail are reported. Surface pressure isotherms with Group I and Group II metal solution subphases indicate increasing interaction of the crown moiety with Ca2+, Na+, K+, Li+/Ba2+ and Mg2+ ions in that order, with mean molecular areas of the effective head group at the surface ranging from 141 angstrom(2) to 219 angstrom(2). The critical micelle concentrations determined by surface tension measurements of the unmetallated ligand and the metallosurfactant are 1.98 mM and 0.66 mM respectively. Wormlike micelles and vesicles are observed with atomic force microscopy after multilayer Langmuir Blodgett film deposition on a glass substrate. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2010.09.036

文献信息

• The influence of varied amide bond positions on hydraphile ion channel activity
  作者：Michelle E. Weber、Wei Wang、Sarah E. Steinhardt、Michael R. Gokel、W. Matthew Leevy、George W. Gokel

  DOI：10.1039/b510863m

  日期：——

  Hydraphile compounds have been prepared in which certain of the amine nitrogens have been replaced by amide residues. The amide bonds are present either in the sidearm, the side chain, or the central relay. Sodium cation transport through phospholipid vesicles mediated by each hydraphile was assessed. All of the amide-containing hydraphiles showed increased levels of Na(+) transport compared to the

  已经制备了亲水化合物，其中某些胺氮已被酰胺残基取代。酰胺键存在于侧臂、侧链或中央中继中。评估了由每个亲水物介导的通过磷脂囊泡的钠阳离子转运。与母体化合物相比，所有含酰胺的亲水物都显示出增加的 Na(+) 运输水平，但观察到侧臂胺到酰胺置换的速率增加最显着。我们将这种增强归因于双层中侧臂的稳定性，以实现更好的离子传导构象。用大肠杆菌和枯草芽孢杆菌对酰胺亲水菌进行的生物学研究表明，只有后者才具有显着的毒性。更远，
• Heterocyclic Amide Hydraphile Synthetic Cation Transporters
  作者：George W. Gokel、Wei Wang、Carl R. Yamnitz

  DOI：10.3987/com-07-s(u)62

  日期：——

  A family of hydraphile ionophores has been prepared in which various approximately CH(2)N approximately to approximately CON approximately replacements have been made to assess the effect on Na(+) transport through phospholipid bilayers. When the central relay (see graphical abstract) was a third macrocycle, symmetrical carbonyl for methylene replacements enhanced activity, but the presence of four or six amide residues diminished transport. When a pair of amides was incorporated into compounds having a 4,4'-bipiperidyl central relay, both significant increases and decreases were observed depending upon the amide positions. The presence of amides alters both the donor group type and strength and the conformation of the structural unit in which it occurs. These changes are shown to depend on the liposomes in which the Na(+) release studies were conducted. These changes are shown to affect the toxicity of the hydraphiles to E. coli.
• Nakano, Akio; Xie, Qingshan; Mallen, Jesus V., Journal of the American Chemical Society, 1990, vol. 112, # 3, p. 1287 - 1289
  作者：Nakano, Akio、Xie, Qingshan、Mallen, Jesus V.、Echegoyen, Luis、Gokel, George W.

  DOI：——

  日期：——
• The influence of aromatic residues in hydraphile spacer units: assay by ion selective electrode methods and in bacteria
  作者：Adam E. Meyer、W. Matthew Leevy、Robert Pajewski、Iwao Suzuki、Michelle E. Weber、George W. Gokel

  DOI：10.1016/j.bmc.2005.01.064

  日期：2005.5

  A small library of hydraphiles has been prepared that incorporates either 1,4-phenylenedioxy or 2,6-naphthalenedioxy within the spacer chains. The side chains attached to the distal macrocycles in these tris(macrocyclic) compounds are either n-dodecyl or benzyl. The presence of the arenes subunits significantly affect sodium cation release from vesicles. The efficacy of ion transport is paralleled by the toxicity of these compounds to Bacillus subtilis. (c) 2005 Elsevier Ltd. All rights reserved.
• A new type of surfactants. The annelides. Characterization of organized metal ion assemblies obtained by cationic complexation at the micelle subsurface
  作者：J. Le Moigne、J. Simon

  DOI：10.1021/j100439a010

  日期：1980.1