2,3-benzo-1,4,7,10,13,16,19,22-octaoxa-2-cyclotetraeicosene | 72216-45-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-benzo-1,4,7,10,13,16,19,22-octaoxa-2-cyclotetraeicosene
• 英文别名: benzo<24>crown-8；Benzo-24-crown-8 ether；benzo-24-crown ether；Benzo-24-crown-8；24-crown-8；B24C8-Benzo crown ether；2,5,8,11,14,17,20,23-octaoxabicyclo[22.4.0]octacosa-1(28),24,26-triene
• CAS: 72216-45-6
• 化学式: C₂₀H₃₂O₈
• 分子量: 400.469
• InChiKey: NJYSMUZHMILTRA-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• 沸点：
  546.2±50.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-benzo-1,4,7,10,13,16,19,22-octaoxa-2-cyclotetraeicosene 在 硝酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 以93%的产率得到4'-nitrobenzo-24-crown-8
  参考文献：
  名称：

  Czech, Anna; Czech, Bronislaw P.; Bartsch, Richard A,, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1841 - 1843

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-bis{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}benzene 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2,3-benzo-1,4,7,10,13,16,19,22-octaoxa-2-cyclotetraeicosene
  参考文献：
  名称：

  Secondary dibenzylammonium ion binding by [24]crown-8 and [25]crown-8 macrocycles

  摘要：

  A range of crown ethers with either [24]crown-8 or [25]crown-8 constitutions have been demonstrated to form pseudorotaxanes with para-disubstituted dibenzylammonium ions, both in solution and in the "gas phase" by H-1 NMR spectroscopy and liquid secondary ion mass spectrometry, respectively. Substitution of the [24]crown-8 framework with increasing numbers of benzo rings is observed to lower the stability constants (K-a's) from >10(3) to similar to 0 M-1 in acetonitrile. A pronounced decrease in K-a values also occurs when the [24]crown-8 constitution is expanded to give a macroring containing 25 atoms - a modification that not only increases the size of the macrocyclic cavity but also disrupts the O-C-C-O repeating unit in the macrocycle's backbone. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00553-5

文献信息

• Host–guest interactions template: the synthesis of a [3]catenane
  作者：Amy L. Hubbard、Gregory J. E. Davidson、Roopa H. Patel、James A. Wisner、Stephen J. Loeb

  DOI：10.1039/b312449e

  日期：——

  Formation of a [3]catenane containing dibenzo-24-crown ether wheels and a large dipyridiniumethane ring is templated by formation of a host-guest adduct between the [3]catenane and the external crown ether.

  通过在[3]环烷与外部冠醚之间形成客体-客体加合物，可以模板化形成包含二苯并24-冠醚轮和大二吡啶鎓乙烷环的[3]环烷。
• FLUORESCENT AROMATIC SENSORS AND THEIR METHODS OF USE
  申请人：Meador Michael A.

  公开号：US20080242870A1

  公开（公告）日：2008-10-02

  Aromatic molecules that can be used as sensors are described. The aromatic sensors include a polycyclic aromatic hydrocarbon core with a five-membered imide rings fused to the core and at least two pendant aryl groups. The aromatic sensor molecules can detect target analytes or molecular strain as a result of changes in their fluorescence, in many cases with on-off behavior. Aromatic molecules that fluoresce at various frequencies can be prepared by altering the structure of the aromatic core or the substituents attached to it. The aromatic molecules can be used as sensors for various applications such as, for example, the detection of dangerous chemicals, biomedical diagnosis, and the detection of damage or strain in composite materials. Methods of preparing aromatic sensor molecules are also described.

  描述了可以用作传感器的芳香分子。这些芳香传感器包括一个多环芳烃核心，该核心上融合了一个五元咪唑环，并且至少有两个侧链芳基基团。这些芳香传感器分子可以通过它们的荧光变化来检测目标分析物或分子应变，许多情况下具有开关行为。可以通过改变芳香核心的结构或连接到其上的取代基来制备在不同频率下发出荧光的芳香分子。这些芳香分子可以用作各种应用的传感器，例如检测危险化学品、生物医学诊断以及复合材料中的损伤或应变的检测。还描述了制备芳香传感器分子的方法。
• [2]Rotaxanes containing pyridinium–phosphonium axles and 24-crown-8 ether wheels
  作者：Norma Georges、Stephen J. Loeb、Jorge Tiburcio、James A. Wisner

  DOI：10.1039/b407653b

  日期：——

  A triethylphosphonium group attached to a pyridinium ethane moiety can be used as an axle for the self-assembly of [2]pseudorotaxanes and [2]rotaxanes. Although [2]pseudorotaxane formation is limited due to the bulk of the PR4+ group, [2]rotaxanes can be formed utilising 24-crown-8 ether, benzo-24-crown-8 ether and naphtho-24-crown-8 ether. The synthesis of these [2]rotaxanes and the X-ray structure of the [2]rotaxane containing a 24-crown-8 ether wheel are described. When the crown ether contains an aromatic group two possible conformational isomers exist; these are identified at low temperature by 1H and 31P NMR spectroscopy.

  一个与吡啶乙烷部分连接的三乙基膦鎓基团可作为[2]假轮烷和[2]轮烷自组装的轴。由于PR4+基团的体积庞大，[2]假轮烷的形成受到限制，但可利用24-冠-8醚、苯并-24-冠-8醚和萘并-24-冠-8醚来形成[2]轮烷。本文描述了这些[2]轮烷的合成，以及含有24-冠-8醚轮的[2]轮烷的X射线结构。当冠醚含有芳香基团时，存在两种可能的构象异构体；通过低温下的1H和31P核磁共振光谱法可以识别这些异构体。
• A Practical Synthesis of Benzocrown Ethers under Phase-Transfer Catalysis Conditions
  作者：Nikolay Lukyanenko、Tatyana Bogaschenko、Stepan Basok、Catherine Kulygina、Alexander Lyapunov

  DOI：10.1055/s-2002-34853

  日期：——

  Convenient and effective procedures for the synthesis of benzo-12-crown-4, benzo-15-crown-5, benzo-18-crown-6, benzo-21-crown-7 and benzo-24-crown-8 under phase-transfer catalysis conditions have been developed.

  苯并-12-皇冠-4、苯并-15-皇冠-5、苯并-18-皇冠-6、苯并-21-皇冠-7和苯并-24-皇冠-8的合成简便有效的程序已经开发了转移催化条件。
• Synthesis, crystal structure, and alkali metal picrate extraction capabilities of molecular clips based on diphenylglycoluril and benzocrown ethers
  作者：Tatiana Yu. Bogaschenko、Alexander Yu. Lyapunov、Leonid S. Kikot'、Alexander V. Mazepa、Mark M. Botoshansky、Marina S. Fonari、Tatiana I. Kirichenko

  DOI：10.1016/j.tet.2012.04.009

  日期：2012.6

  A convenient method for the synthesis of a series of molecular clips based on the diphenylglycoluril framework and benzocrown ether moieties by the reaction of bis(cyclomethoxymethylene)diphenylglycoluril with benzocrown ethers in polyphosphoric acid is proposed. X-ray diffraction analysis of molecular clips with the benzo-12-crown-4 and benzo-15-crown-5 fragments showed that both compounds are chloroform

  提出了一种方便的方法，通过双（环甲氧基亚甲基）二苯基甘脲与苯并冠醚在多磷酸中的反应，合成基于二苯基甘脲的骨架和苯并冠醚部分的一系列分子夹。用苯并-12-冠-4和苯并-15-冠-5片段进行的分子夹的X射线衍射分析表明，两种化合物均为化学计量夹为氯仿1：1的氯仿溶剂化物。通过理论和实验方法在获得的剪取物的存在的抗-抗构象被证明。通过FABMS光谱法和萃取实验检查了所得分子夹对碱金属和铵离子的络合性能。