N-benzyl-4,13-diaza-18-crown-6 | 94605-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-4,13-diaza-18-crown-6
• 英文别名: monobenzyldiaza-18-crown-6；1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane, 7-(phenylmethyl)-；7-benzyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 94605-71-7
• 化学式: C₁₉H₃₂N₂O₄
• 分子量: 352.474
• InChiKey: SPCITAITJXDNPB-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C(Solv: hexane (110-54-3))
• 沸点：
  490.2±40.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  52.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyl-4,13-diaza-18-crown-6 在 palladium on activated charcoal 氢气 、 sodium carbonate 、 potassium iodide 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、482.63 kPa 条件下， 反应 96.0h， 生成 N,N'-bis[12-(diaza-18-crown-6)dodecyl]-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：

  9-[(4-methylphenyl)sulfonyl]-3,6,12,15-tetraoxa-9-aza-1,17-heptadecanediol 在 吡啶 、 lithium aluminium tetrahydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 168.0h， 生成 N-benzyl-4,13-diaza-18-crown-6
  参考文献：
  名称：

  Ditopic receptors capable of hydrogen bonding: Synthesis and complexation behaviour of diaza crown-ethers having melamine sidearms

  摘要：

  The new ditopic receptors 1-3 (Figure 1) have been synthesized and their binding ability for alkaline and transition metal cations has ben investigated by halide and W-Vis titrations. The recognition of complementary molecules through hydrogen bonding has been studied by H-1-NMR. The simultaneous recognition of these two guests is an anti-cooperative event. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00573-6

文献信息

• Syntheses of unsymmetrically N,N'-bis(substituted)-4,13-diaza-18-crown-6-ether derivatives as a new electron donor-spacer-acceptor triad
  作者：Minoru Morimoto、Keijiro Fukui、Norioki Kawasaki、Tomokazu Iyoda、Takeo Shimidzu

  DOI：10.1016/s0040-4039(00)60066-7

  日期：1993.1

  A simple and general synthetic strategy potentially applicable for the preparation of a wide variety of unsymmetrically N,N'-bis(substituted)-4, 13-diaza-18-crown-6-ether derivatives was reported.

  报道了一种简单且通用的合成策略，该策略可能适用于制备各种不对称的N，N'-双（取代）-4，13-二氮杂-18-皇冠-6-醚衍生物。
• Evidence for multiple alkali metal cation complexation in membrane-spanning ion transporters
  作者：Hossein Shabany、Clare L. Murray、George W. Gokel、Charles A. Gloeckner、Michael A. Grayson、Michael L. Gross

  DOI：10.1039/b005442i

  日期：——

  The polynitrogen-containing cation transporters 1–4 are shown by electrospray mass spectrometry to form multi-cationic species. In the absence of Na+, protonated species dominate but increasing the sodium concentration leads to all binding sites being occupied.

  多氮含阳离子转运蛋白1–4通过电喷雾质谱法被显示形成多阳离子物种。在没有Na+的情况下，质子化物种占主导地位，但增加钠浓度会导致所有结合位点被占据。
• [EN] COMPOSITIONS AND METHODS FOR SYNTHETIC AMPHIPHILE-INDUCED CHANGES IN PLANT ROOT MORPHOLOGY<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR MODIFICATIONS DE MORPHOLOGIE DE RACINES DE PLANTE INDUITES PAR AMPHIPHILE SYNTHÉTIQUE
  申请人：UNIV MISSOURI

  公开号：WO2016022991A1

  公开（公告）日：2016-02-11

  The disclosure provides a method for increasing the lateral root development of a plant by exposing said plant to a composition containing a synthetic amphiphile. By increasing the number of lateral roots, the surface area of the root structure is increased, making the plants better able to survive such stresses as drought or low nutrients

  该公开提供了一种通过将植物暴露在含有合成两性分子的组合物中来增加植物侧根发育的方法。通过增加侧根的数量，根结构的表面积增加，使植物更能够抵抗干旱或低营养等压力。
• Synthetic Ion Channel Activity Documented by Electrophysiological Methods in Living Cells
  作者：W. Matthew Leevy、James E. Huettner、Robert Pajewski、Paul H. Schlesinger、George W. Gokel

  DOI：10.1021/ja046626x

  日期：2004.12.1

  Hydraphiles are synthetic ion channels that use crown ethers as entry portals and that span phospholipid bilayer membranes. Proton and sodium cation transport by these compounds has been demonstrated in liposomes and planar bilayers. In the present work, whole cell patch clamp experiments show that hydraphiles integrate into the membranes of human embryonic kidney (HEK 293) cells and significantly

  Hydraphiles 是合成离子通道，使用冠醚作为入口并跨越磷脂双层膜。这些化合物的质子和钠阳离子传输已在脂质体和平面双层中得到证实。在目前的工作中，全细胞膜片钳实验表明亲水胶整合到人胚胎肾 (HEK 293) 细胞的膜中并显着增加膜电导。膜通透性的改变是可逆的，研究中的细胞在实验过程中仍然至关重要。太短（C(8)-苄基通道）无法跨越双层或由于中央继电器缺陷而处于非活动状态的对照化合物不会引起类似的电导增加。对照实验证实非活性通道类似物不显示非特异性效应，例如激活天然通道。
• The effect of twin-tailed sidearms on sodium cation transport in synthetic hydraphile cation channels
  作者：Hossein Shabany、Robert Pajewski、Ernesto Abel、Anindita Mukhopadhyay、George W. Gokel

  DOI：10.1002/jhet.5570380623

  日期：2001.11

  The preparation of novel tris(macrocycle)s that transport Na+ through phospholipid bilayers is reported. All of the reported structures have the following structural elements: sidechain-macrocycle-spacer-macro-cycle-spacer-macrocycle-sidechain. The overall extension of the channel system is defined by the lengths of the spacer chains. The flexible sidearms are thought to be aligned with the lipid axis

  据报道，新型Tris（大环）可通过磷脂双层转运Na +。所有报告的结构均具有以下结构元素：侧链-大环-间隔子-大环-循环-大环-侧链。通道系统的整体延伸范围由间隔链的长度决定。柔性侧臂被认为与脂质轴对齐并且与间隔链相反。在一定程度上，间隔链有助于结构的组织以及将含阳离子的孔与周围的脂质链隔离，更多的疏水链有望增强阳离子的运输。C 12 H 25 （CH 2）12 （CH2）12 Ç 12 ħ 25，1，用（C 12 H ^ 25）2 N（CH 2）2 （CH 2）12 （CH 2）12 （CH 2） 2N（C 12 H ^ 25）2，图11，示出了的Na +转运，着实增强。