1,11-bis(4-hydroxyphenoxy)-3,6,9-trioxaundecane | 14556-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,11-bis(4-hydroxyphenoxy)-3,6,9-trioxaundecane
• 英文别名: 4-[2-[2-[2-[2-(4-Hydroxyphenoxy)ethoxy]ethoxy]ethoxy]ethoxy]phenol
• CAS: 14556-10-6
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: VMJYZHIKFOGCHO-UHFFFAOYSA-N

物化性质

• 沸点：
  551.2±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,11-bis(4-hydroxyphenoxy)-3,6,9-trioxaundecane 在 咪唑 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,11-bis<4-<2-(2-(2-(2-triisopropylsilyloxyethoxy)ethoxy)ethoxy)ethoxy>phenoxy>-3,6,9-trioxaundecane
  参考文献：
  名称：

  分子穿梭机

  摘要：

  本通讯中描述的分子穿梭机是构建更复杂分子组装的原型，其中组件将被设计为以高度可控的方式接收、存储、传输和传输信息，并在超分子水平上进行自发自组装. 越来越多地，我们可以期待一种“自下而上”的纳米技术方法，其目标是开发分子级信息处理系统

  DOI：

  10.1021/ja00013a096
• 作为产物：
  描述：

  1,11-bis<4-(benzyloxy)phenoxy>-3,6,9-trioxaundecane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 以99%的产率得到1,11-bis(4-hydroxyphenoxy)-3,6,9-trioxaundecane
  参考文献：
  名称：

  Molecular meccano. 1. [2]Rotaxanes and a [2]catenane made to order

  摘要：

  A new synthetic strategy for the elaboration of supramolecular species and molecular compounds containing noncovalently interacting components is described, with the long-term objective of constructing highly ordered, wholly synthetic assemblies from readily available starting materials. These could serve as a basis for the future development of mechanoelectrical and photoelectrical communication systems and devices capable of storing and processing information. The approach was conceived against a background of a quarter of a century's experience in supramolecular, alias host-guest, chemistry. It is based on the use of irreversibly interlocked molecular systems that take the form of catenanes and rotaxanes. Such compounds are seen to be the ideal vehicles through which to transfer from supramolecular and host-guest chemistry the knowledge and experience gained from studying complexes between small chemical entities to very much larger molecular assemblies. Once we know how to interlock molecular components irreversibly and efficiently, we shall have a very much clearer idea on how to intertwine related polymer chains reversibly. A number of template-directed syntheses of [2]rotaxanes and a [2]catenane is discussed. They illustrate that there are inherently simple ways of making apparently complex unnatural products from appropriate substrates without the need for reagent control or catalysis. The noncovalent bonding interactions that are used to self-assemble the 1:1 complexes, which serve as precursors to the rotaxanes and the catenane, as well as to the [2]rotaxanes and the [2]catenane themselves, ''live on'' in their structures and superstructures after the self-assembly process is complete. A variety of methods, including X-ray crystallography, fast atom bombardment mass spectrometry, ultra violet-visible, luminescence, nuclear magnetic resonance, and electron spin resonance spectroscopies, and electrochemistry, demonstrate the high structural order that is incorporated into these new molecular assemblies in both the solid and solution states.

  DOI：

  10.1021/ja00027a027

文献信息

• Towards mechanically linked polyrotaxanes by sequential deprotection–coupling steps of bifunctional rotaxanes
  作者：Michel P. L. Werts、Maarten van den Boogaard、Georges Hadziioannou、Gerasimos M. Tsivgoulis

  DOI：10.1039/a900914k

  日期：——

  The monomer rotaxane 13, bearing two protected functional groups, is used to obtain a dimer, following a new approach of sequential deprotection–coupling steps which can lead to mechanically linked polyrotaxanes.

  单体旋转烷（rotaxane）13，含有两个保护的功能团，用于获取一个二聚体，采用一种新的顺序去保护-耦合步骤的方法，这可以导致机械连接的聚旋转烷（polyrotaxanes）的形成。
• The template-directed synthesis of porphyrin-stoppered [2]rotaxanes
  作者：Peter R. Ashton、Martin R. Johnston、J. Fraser Stoddart、Malcolm S. Tolley、John W. Wheeler

  DOI：10.1039/c39920001128

  日期：——

  Two [2]rotaxanes, composed of (i) a polyether chain intercepted by (a) one centrally-located and (b) two symmetrically-located π-electron-rich hydroquinol rings and terminated by free-base and metallated (Zn) tetraaryl-porphyrin groups respectively and (ii) a tetracationic cyclophane constructed of two π-electron-deficient bipyridinium units linked by paraphenylenedimethyl residues, have been self-assembled by a clipping procedure.

  两种[2]旋转烷，由以下部分组成：(i) 一个聚醚链，中间位置有一个和两个对称位置的富 π 电子的氢醌环，末端分别为游离碱和金属化（锌）四芳基卟啉基团；(ii) 一个四阳离子环烷，由两个富 π 电子缺陷的二吡啶单元通过对苯二甲基残基连接而成。通过夹持过程自组装而成。
• Self-Assembly of Novel [3]- and [2]Rotaxanes with Two Different Ring Components:  Donor−Acceptor and Hydrogen Bonding Interactions and Molecular-Shuttling Behavior
  作者：Xin Zhao、Xi-Kui Jiang、Min Shi、Yi-Hua Yu、Wei Xia、Zhan-Ting Li

  DOI：10.1021/jo010497a

  日期：2001.10.1

  Three of the first kind of hetero[3]rotaxanes, which comprise one linear component and one neutral and one tetracationic ring component, have been assembled by using the intermolecular hydrogen bonding and donor-acceptor interactions. Three neutral [2]rotaxanes and three tetracationic [2]rotaxanes have also been synthesized as intermediate products or for the sake of property comparison. The linear

  通过使用分子间氢键和供体-受体相互作用，组装了三种第一类杂[3]轮烷，它们分别包含一个线性成分和一个中性及一个四阳离子环成分。为了中间性或出于性能比较的目的，还合成了三种中性[2]轮烷和三种四阳离子[2]轮烷。线性分子中掺有两个甘氨酸亚基，用于中性四酰胺环烷的模板化；以及一个或两个氢醌亚基，用于诱导四阳离子环烷的形成。可变温度（1）H NMR研究表明，四阳离子环组分沿线性组分的穿梭行为基本上受中性环组分的存在的影响。中性环在缺电子的四阳离子环上的空间排斥相互作用同时减弱了后者在线性组分的两个富电子对苯二酚位置上的“定位”趋势。结果，与相应的中性无环[2]轮烷的穿梭过程相比，与两个氢醌位点之间的四阳离子环的穿梭过程相关的活化能显着降低。第一次，通过可变温度（1）H NMR光谱研究了二吡啶鎓亚基绕由连接它们的四亚甲基环内的两个亚甲基形成的轴的旋转，并且还成功获得了相关的动力学数据。此外，研究了
• [2]Catenane Assembly from Calix[4]arene Crown Ethers
  作者：Zhan-Ting Li、Xiu-Lian Zhang、Xiong-Dong Lian、Yi-Hua Yu、Yi Xia、Cheng-Xue Zhao、Zhang Chen、Zhi-Ping Lin、Huan Chen

  DOI：10.1021/jo000196l

  日期：2000.8.1

  A variety of novel calix[4]arene-incorporating crown ethers with or without intramolecular hydrogen bonding have been prepared by two efficient methods and utilized as donor rings to assemble calix[4]arene [2]catenanes based on pi-stacking interaction between hydroquinone and bipyridinium units. Treatment of calix[4]arene crown ethers 4, 10a, or 10b, whose cone conformation was fixed by intramolecular

  通过两种有效方法制备了多种带有或不带有分子内氢键的新型杯芳烃[4]芳烃结合冠醚，并基于氢醌之间的π-堆积相互作用，用作供体环来装配杯芳烃[4]芳烃[2]邻苯二酚。和联吡啶单元。用指示盐15 x 2PF6和二溴化物16处理杯[4]亚芳基冠醚4、10a或10b，其圆锥构象通过分子内氢键固定在杯[4]亚芳烃部分中，用指示盐15 x 2PF6和二溴化物提供相应的[2]邻苯二甲酸酯17a x 4PF6、17b x 4PF6和17c x 4PF6的产率分别为20％，53％和55％，而15 x 2PF6和二溴化物16在具有构象柔性的11或12和锥构象的情况下的反应保留有两个丙基的[2]儿茶素18 x 4PF6和19 x 4PF6的产率分别为12％和6％。[2]邻苯二甲酸酯21a x 4Cl，21b x 4Cl和21c x 4Cl，在供体和受体环中均结合了杯[4]亚芳基，也成功地由10a或10b，16和除盐20a
• Towards a Molecular Anchor Chain. Synthesis and Catenations of Spiro Crown Ethers
  作者：Peter R. Ashton、Thomas Horn、Stephan Menzer、Jon A. Preece、Neil Spencer、J. Fraser Stoddard、David J. Williams

  DOI：10.1055/s-1997-4467

  日期：1997.4

  Two new crown ethers (1 and 2) featuring a spiro linked assembly of two to three individual macrorings have been synthesised. The syntheses were achieved by means of high dilution techniques and blocking/deblocking procedures, beginning with pentaerythritol as the basic building block. The spiro and dispiro crown ethers 1 and 2 participate in template-directed self-assembly reactions with 1,1'-[1,4-phenylenebis(methylene)bis]-4,4'-bipyridinium bis(hexafluorophosphate) and 1,4-bis(bromomethyl)benzene at either one or both recognition sites. The resulting new [2]catenanes (12 ⋅ 4PF6 and 14 ⋅ 4PF6) and bis[2]catenanes (13 ⋅ 8PF6 and 15 ⋅ 8PF6), incorporating interlocked cyclobis(paraquat-p-phenylene) tetracations, were characterised by (dynamic) NMR spectroscopy and high resolution FAB mass spectrometry. The X-ray crystal structure of one of these spiro-linked bis[2]catenanes, namely 13 ⋅ 8PF6, is reported.

  我们合成了两种新的冠醚（1 和 2），其特点是由两到三个单独的大环组成的螺链组合。以季戊四醇为基本组成单元，通过高稀释技术和封端/解封端程序进行合成。螺和二螺冠醚 1 和 2 与 1,1'-[1,4-亚苯基双（亚甲基）双]-4,4'-联吡啶鎓双六氟磷酸盐和 1,4-双（溴甲基）苯在一个或两个识别位点上发生了模板定向自组装反应。通过（动态）核磁共振光谱法和高分辨率 FAB 质谱法，对由此产生的新[2]卡替萘烷（12 ⋅ 4PF6 和 14 ⋅ 4PF6）和双[2]卡替萘烷（13 ⋅ 8PF6 和 15 ⋅ 8PF6）进行了表征。报告了其中一种螺联双[2]烯烃（即 13 ⋅ 8PF6）的 X 射线晶体结构。