1,4-bis(tosyloxyethoxy)benzene | 37108-78-4

• 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: 1,4-bis(tosyloxyethoxy)benzene
• 英文别名: hydroquinone 2,2'-bis(tosylethyl) ether；1,4-bis(oxy-2-tosyloxyethyl)-benzene；ditosylate；p-bis(2'-tosyloxyethoxy)benzene；2,2'-[1,4-phenylenebis(oxy)]bis(ethane-2,1-diyl)bis(4-methylbenzenesulfonate)；2-[4-[2-(4-Methylphenyl)sulfonyloxyethoxy]phenoxy]ethyl 4-methylbenzenesulfonate
• CAS: 37108-78-4
• 化学式: C₂₄H₂₆O₈S₂
• 分子量: 506.598
• InChiKey: KCEQEBVOQAQPMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4-bis(tosyloxyethoxy)benzene 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 61.0h， 生成 (S)-1-(2-{4-[2-((S)-2-Hydroxy-propoxy)-ethoxy]-phenoxy}-ethoxy)-propan-2-ol
  参考文献：
  名称：

  Constitutionally Asymmetric and Chiral [2]Pseudorotaxanes¹

  摘要：

  The self-assembly and characterization of a range of chiral pseudorotaxanes has been explored using chiroptical methods. The syntheses of (i) constitutionally asymmetric acyclic hydroquinone-containing polyethers and (ii) optically active hydroquinone-containing acyclic polyethers, bearing pairs of methyl or isobutyl groups related to each other in a C-2-symmetric manner within the polyether backbone, are described. The combination of (i) the tetracationic cyclophane cyclobis(paraquat-p-phenylene) tetrakis(hexafluorophosphate), possessing a pi-electron deficient cavity, and (ii) the linear noncentrosymmetric acyclic polyethers produces [2]pseudorotaxanes that have been characterized by H-1 NMR, UV/vis and circular dichroism (CD) spectroscopies in solution and by X-ray crystallography in the solid state. The introduction of constitutional asymmetry or chirality gives rise to a number of different geometries for the [2]pseudorotaxanes in both the solution and solid states. in particular, CD-spectroscopic measurements on the optically active [2]pseudorotaxanes have shown that-depending on the positions of the C-2 symmetrically related chiral centers in the polyether chains with respect to the hydroquinone rings-the chirality present in the pi-electron rich threadrike guest can induce chirality that is associated with the supramolecular structure as a whole, resulting in a chiral charge-transfer transition involving not only the pi-donors in the chiral guests but also the pi-acceptors in the achiral host.

  DOI：

  10.1021/ja970018i
• 作为产物：
  描述：

  对苯二酚 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 1,4-bis(tosyloxyethoxy)benzene
  参考文献：
  名称：

  Synthesis of Alkyl-substituted, Strapped Porphyrin to Prepare Stable Alkyl-chain-assisted Self-assembled Monolayers of Porphyrin Conjugates

  摘要：

  我们合成了一种烷基取代的带状卟啉，旨在制备稳定的烷基链辅助卟啉共轭物自组装单层（SAM）。我们通过扫描隧道显微镜（STM）证实，合成的带状卟啉可以形成稳定的 SAM。这种方法将通过在捆绑分子中引入各种官能团，实现烷基链辅助 SAM 的功能化。

  DOI：

  10.1246/cl.2004.1418

文献信息

• Synthesis and Evaluation of Bis-Thiazolium Salts as Potential Antimalarial Drugs
  作者：Sergio A. Caldarelli、Jean-Frédéric Duckert、Sharon Wein、Michèle Calas、Christian Périgaud、Henri Vial、Suzanne Peyrottes

  DOI：10.1002/cmdc.201000097

  日期：——

  the structural requirements of the linker that lead to more rigid analogues with fewer rotatable bonds but which retain antimalarial activity, a new series of compounds incorporating an aryl moiety and eventually oxygen atoms were prepared, and their biological activity was evaluated. Structure–activity relationships suggest that the optimal linker construct is an aromatic group with two n‐butyl chains

  先前已设计出一种基于使用双效衍生物的创新治疗方法，以抑制疟原虫中磷脂酰胆碱的生物合成。 spp。其中，双噻唑鎓盐在低纳摩尔浓度范围内能阻止疟原虫的增殖。但是，由于不合适的分子特性，例如两个极性头的存在和接头的柔韧性，这些化合物的口服生物利用度低。为了表征导致更刚性的类似物，具有更少的可旋转键但保留抗疟活性的接头的结构要求，制备了一系列新的包含芳基部分并最终引入氧原子的化合物，并对其生物学活性进行了评估。结构与活性之间的关系表明，最佳的连接子结构是在对位上有两个正丁基链分支的芳族基团。两个新的线索（化合物选择39和40进行进一步开发。
• Chelidamic acid derivatives: Precursors to functionalized pyridyl cryptands & functionalized metal ligands
  作者：Harry W. Gibson、Terry L. Price、Adam M.-P. Pederson、Zhenbin Niu、Pothanagandhi Nellipalli

  DOI：10.1016/j.tet.2021.132333

  日期：2021.8

  materials, functionalization is required; in this article we describe syntheses of 23 new chelidamic acid (2,6-dicarboxy-4-hydroxypyridine, 5) derivatives that can be used to prepare functional pyridyl cryptands and functional metal ligands. The preparation and characterization of three new functionalized pyridyl cryptands are also included.

  吡啶基穴状配体，如12 - 16从吡啶-2,6-二羰基氯（形成4）和冠醚二醇7 - 11，已被证明是优异的紫精主机（N，N' -二烷基-4,4' -联吡啶鎓盐，2 ) K a值为~10 4至10 6  M -1，因此被认为是超分子系统的理想构件。然而，为了将这些宿主基序整合到有用的起始材料中，需要进行功能化；在本文中，我们描述了 23 种新螯合胺酸（2,6-二羧基-4-羟基吡啶，5 ) 可用于制备功能性吡啶基穴状配体和功能性金属配体的衍生物。还包括三个新的功能化吡啶基穴状配体的制备和表征。
• Synthesis of Novel Receptors From 7-Deoxycholic Acid and Studies on Their Cation Binding Properties
  作者：Vijay Nair、Jaya Prabhakaran、Guenter K. Eigendorf

  DOI：10.1080/00397919708005015

  日期：1997.9

  The synthesis and cation binding properties of chiral crown ethers derived from 7-deoxycholic acid along with their application in asymmetric Michael reaction are described.

  描述了衍生自 7-脱氧胆酸的手性冠醚的合成和阳离子结合特性及其在不对称迈克尔反应中的应用。
• Dinuclear zinc(ii) dithiocarbamate macrocycles: ditopic receptors for a variety of guest molecules
  作者：Wallace W. H. Wong、David Curiel、Andrew R. Cowley、Paul D. Beer

  DOI：10.1039/b415935g

  日期：——

  reveal a correlation between the strength of complexation and complementary receptor cavity : guest molecule size. In particular, the X-ray structure of a 1 : 1 host–guest complex between a dinuclear zinc(II) dtc receptor and DABCO illustrates the cooperative nature in which the dinuclear receptor associates with the bidentate guest.

  一系列双核的合成 二硫代氨基甲酸锌（II） （dtc）含有的大环受体 芳基报告了不同尺寸的间隔基。从1 H NMR滴定研究中可以看出，这些受体具有结合各种中性和阴离子性双齿客体物种的能力，包括1,4-二氮杂双环[2.2.2]辛烷（DABCO），异烟酸酯和对苯二甲酸酯以1：1分子内包合物的形式存在。稳定性常数的测定揭示了络合强度与互补受体腔：客体分子大小之间的相关性。尤其是，双核锌（II）dtc受体与DABCO之间的1：1主客复合物的X射线结构说明了双核受体与双齿客体缔合的合作性质。
• Electrochemical Synthesis and Properties of Poly[1,4-bis(<i>N</i>-pyrrolylalkoxy)benzene]s with a Three-dimensional Crosslinked Structure
  作者：Katsuhiko Ono、Satsuki Yamada、Masakazu Ohkita、Katsuhiro Saito、Shoji Tanaka、Takamasa Hanaichi

  DOI：10.1246/cl.2003.516

  日期：2003.6

  The title polymers, which were composed of π-conjugated pyrroles and dialkoxybenzene crosslinkers, were prepared by electrochemical polymerization to afford uniform thin films. These films were characterized by cyclic voltammetry (CV), scanning electron microscope (SEM), and redox stability.

  由π-共轭吡咯和二烷氧基苯交联剂组成的标题聚合物通过电化学聚合制备以提供均匀的薄膜。这些薄膜的特征在于循环伏安法 (CV)、扫描电子显微镜 (SEM) 和氧化还原稳定性。