2,3,8,9,14,15,20,21-tetrabenzo-24-crown-8 | 14098-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,8,9,14,15,20,21-tetrabenzo-24-crown-8
• 英文别名: tetrabenzo-24-crown-8；tetrabenzo[24]crown-8；TB24C8；2,5,12,15,22,25,32,35-Octaoxapentacyclo[34.4.0.06,11.016,21.026,31]tetraconta-1(40),6,8,10,16,18,20,26,28,30,36,38-dodecaene
• CAS: 14098-25-0
• 化学式: C₃₂H₃₂O₈
• 分子量: 544.601
• InChiKey: KFBWZNOWOCNKRF-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  665.9±55.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,3,8,9,14,15,20,21-tetrabenzo-24-crown-8 、 dibenzylammonium hexafluorophosphate 以 氘代氯仿 、 氘代乙腈 为溶剂， 生成 C₃₂H₃₂O₈*C₁₄H₁₅N*F₆P^(1-)*H⁽¹⁺⁾
  参考文献：
  名称：

  The effect of pressure on pseudorotaxane formation by using the slipping method

  摘要：

  By using high-pressure conditions the Formation Of pseudorotaxane via the slipping approach is accelerated. Analysis of the effects of pressure on the rate constants affords activation Volumes for the pseudorotaxane forming slipping reactions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.107
• 作为产物：
  描述：

  O,O-双(2-羟基乙氧基)苯 在 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.0h， 生成 2,3,8,9,14,15,20,21-tetrabenzo-24-crown-8
  参考文献：
  名称：

  聚苯并冠醚：通过铯辅助环化和固态结构合成

  摘要：

  通过铯辅助环化反应制备了一系列大环聚苯并冠醚。二酚/双酚、低聚乙二醇的二甲磺酸盐和碳酸铯在 MeCN 中的反应以高产率产生大环聚苯并冠醚。为了进一步了解这些化合物的结构，通过 X 射线衍射获得了三个大环冠醚的固态结构。

  DOI：

  10.3998/ark.5550190.0011.717

文献信息

• Preparation of benzo- and polybenzocrown ethers by macrocyclization reactions
  作者：Robert E. Hanes、Jong Chan Lee、Sheryl N. Ivy、Anna Palka、Richard A. Bartsch

  DOI：10.3998/ark.5550190.0011.718

  日期：——

  the method was used for the preparation of monobenzocrown ethers. Interestingly, for the preparation of monobenzocrown ethers, [2+2] adducts were discovered to be significantly contaminating the products. Dimesylates were chosen as the leaving group due to their ease or preparation and the ability to use the unpurified products with no apparent impact on the macrocyclization.

  探索了冠醚的大环化及其制备方法。我们提出了一种稳健、可扩展的方法来制备这些大环。此外，研究了改变前体结构的影响，以确定双酚和二甲磺酸酯的“切割”是否影响反应过程，如通过产率测量的。此外，使用儿茶酚衍生物，该方法用于制备单苯并冠醚。有趣的是，在制备单苯并冠醚时，发现 [2+2] 加合物严重污染了产品。选择二甲磺酸盐作为离去基团是因为它们易于制备，并且能够使用未纯化的产物而对大环化没有明显影响。
• Anticoccidial activity of crown polyethers
  作者：George R. Brown、Alan J. Foubister

  DOI：10.1021/jm00358a025

  日期：1983.4

  Anticoccidial activity in vitro against Eimeria tenella is reported for crown polyethers with ring sizes from 14 to 30 atoms. The most potent compounds, 4 and 9, were found active at 0.33 ppm, but none were active in vivo. Test results are discussed in terms of lipophilic shielding of complexed cations.
• Effect of Pressure on [2]Pseudorotaxane Formation and Decomplexation and Their Corresponding Activation Volumes
  作者：Yuji Tokunaga、Nanae Wakamatsu、Norihiro Ohiwa、Osamu Kimizuka、Akihiro Ohbayashi、Koichiro Akasaka、Susumu Saeki、Kenji Hisada、Tatsuhiro Goda、Youji Shimomura

  DOI：10.1021/jo1003955

  日期：2010.8.6

  In this study, we investigated the effect of pressure on the formation and decomplexation of [2]pseudorotaxanes. High pressure accelerated the formation of [2]pseudorotaxanes in an aprotic nonpolar solvent (CDCl3/CD3CN) via the slipping approach when using two crown ether/secondary ammonium salt systems: dibenzo[24]crown-8/bis(cyclohexylmethyl)ammonium salt (1a/2a) and tetrabenzo[24]crown-8/dibenzylammonium salt (1b/2b). The influence of pressure on the rate constants for the formation of the [2]pseudorotaxanes 3a and 3b revealed activation volumes (Delta V double dagger) of -2.5 and -4.6 cm(3) mol(-1), respectively, at 303 K and zero pressure. We also investigated the effect of pressure on the decomplexation of the [2]pseudorotaxanes 3a and 3b in a polar solvent (DMSO-d(6)/CDCl3), obtaining activation volumes of -0.9 and -0.4 cm(3) mol(-1), respectively, at 303 K and zero pressure. Moreover, we calculated the activation parameters for the decomplexation processes on the basis of transition state theory at each pressure.
• BROWN, G. R.;FOUBISTER, A. J., J. MED. CHEM., 1983, 26, N 4, 590-592
  作者：BROWN, G. R.、FOUBISTER, A. J.

  DOI：——

  日期：——
• US4110363A
  申请人：——

  公开号：US4110363A

  公开（公告）日：1978-08-29