4,4',5,5'-tetraiododibenzo-24-crown-8 ether | 875325-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4',5,5'-tetraiododibenzo-24-crown-8 ether
• 英文别名: 4,4',5,5'-tetraiododibenzo[24]crown-8；4,5,4',5'-tetraiododibenzo-24-crown-8；14,15,30,31-Tetraiodo-2,5,8,11,18,21,24,27-octaoxatricyclo[26.4.0.012,17]dotriaconta-1(32),12,14,16,28,30-hexaene；14,15,30,31-tetraiodo-2,5,8,11,18,21,24,27-octaoxatricyclo[26.4.0.012,17]dotriaconta-1(32),12,14,16,28,30-hexaene
• CAS: 875325-91-0
• 化学式: C₂₄H₂₈I₄O₈
• 分子量: 952.1
• InChiKey: HDKYSRYCCQAFII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4,4',5,5'-tetraiododibenzo-24-crown-8 ether 、 4-叔-丁基苯基乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以75%的产率得到4,4',5,5'-tetra(4-tert-butylphenylethynyl)dibenzo-24-crown-8 ether
  参考文献：
  名称：

  An efficient synthesis of 4,4′,5,5′-tetraiododibenzo-24-crown-8 and its highly conjugated derivatives

  摘要：

  4,4',5,5'-Tetraiododibenzo-24-crown-8 (9), a practical building block, was prepared under efficient and mild reaction conditions starting from the simple starting material, catechol (1). Highly conjugated 4,4',5,5'-tetraethynyldibenzo-24-crown-8 (10a,b) were prepared via a Sonogashira, coupling reaction from tetraiodocrown ether 9. These highly conjugated crown ethers form complexes in CD2Cl2 with dibenzylammonium hexafluorophosphate in a 1:1 ratio. Emission spectrum of pseudorotaxane 11 shows a dramatic shift from the non-complexed precursor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.147
• 作为产物：
  描述：

  2,2-二甲基-1,3-苯并二恶茂烷 在 盐酸 、 mercury(II) diacetate 、 碘 、 caesium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 50.0h， 生成 4,4',5,5'-tetraiododibenzo-24-crown-8 ether
  参考文献：
  名称：

  An efficient synthesis of 4,4′,5,5′-tetraiododibenzo-24-crown-8 and its highly conjugated derivatives

  摘要：

  4,4',5,5'-Tetraiododibenzo-24-crown-8 (9), a practical building block, was prepared under efficient and mild reaction conditions starting from the simple starting material, catechol (1). Highly conjugated 4,4',5,5'-tetraethynyldibenzo-24-crown-8 (10a,b) were prepared via a Sonogashira, coupling reaction from tetraiodocrown ether 9. These highly conjugated crown ethers form complexes in CD2Cl2 with dibenzylammonium hexafluorophosphate in a 1:1 ratio. Emission spectrum of pseudorotaxane 11 shows a dramatic shift from the non-complexed precursor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.147

文献信息

• Colour coding the co-conformations of a [2]rotaxane flip-switch
  作者：Natalie D. Suhan、Laura Allen、Mireille T. Gharib、Elizabeth Viljoen、Sarah J. Vella、Stephen J. Loeb

  DOI：10.1039/c1cc10948k

  日期：——

  Fine-tuning the charge transfer chromophores in a series of [2]rotaxane flip-switches yields a unique optical signal (purple colour) for one of the interactions allowing for facile determination of the position of the flip-switch equilibrium.

  在一系列 [2]rotaxane 翻转开关中微调电荷转移颜色团，产生了独特的光学信号（紫色），用于一种相互作用，从而便于确定翻转开关平衡的位置。
• A Tubular Belt and a Möbius Strip with Dynamic Joints: Synthesis, Structure, and Host–Guest Chemistry
  作者：Jun Yuan、Yunyi Song、Xia Li、Jialin Xie、Shengyi Dong、Kelong Zhu

  DOI：10.1021/acs.orglett.1c03781

  日期：2021.12.17

  Two unprecedented isomeric macrocycles, a tubular belt and a Möbius strip, with thianthrene joints have been constructed through a one-step cyclization reaction. Both structures are fully characterized by NMR spectroscopy, mass spectrometry, and single-crystal X-ray diffraction. A complexation study reveals that the tubular belt is a container for electron deficient guests. The Möbius strip exhibits

  通过一步环化反应构建了两个前所未有的异构大环，一个管状带和一个莫比乌斯带，带有噻蒽接头。两种结构均通过 NMR 光谱、质谱和单晶 X 射线衍射进行了充分表征。一项络合研究表明，管状带是缺电子客人的容器。莫比乌斯带表现出扭曲迁移动力学，可以通过钠离子进行调节。它们的简便合成、独特的结构和多样化的主客体化学丰富了带化学。
• Synthesis, structure, and host-guest chemistry of a pair of isomeric selenanthrene-bridged molecular cages
  作者：Wanqian Lv、Yunyi Song、Xinyuan Lv、Jun Yuan、Kelong Zhu

  DOI：10.1016/j.cclet.2023.108179

  日期：2023.2

  of selenanthrene-bridged molecular cages have been constructed through a one-step cyclization reaction of a tetrakis(iodo) crown ether with selenium powder. The tubular belt-shaped cage has an intrinsic cavity which can adaptively transform to accommodate electron-deficient guests forming [2]pseudorotaxane complexes. The other product was determined to be an isomeric cage featuring a Möbius strip structure

  通过四（碘）冠醚与硒粉的一步环化反应，构建了一对硒桥联分子笼。管状带状笼具有一个内在的空腔，可以自适应地转变以容纳形成[2]拟轮烷复合物的缺电子客体。另一种产品被确定为具有莫比乌斯带结构的异构笼，其表现出比噻蒽对应物更慢的扭转迁移动力学。使用硒蒽作为接头的成功为分子笼的结构设计和性能调控提供了一种替代方法。
• An efficient synthesis of 4,4′,5,5′-tetraiododibenzo-24-crown-8 and its highly conjugated derivatives
  作者：Joshua J. Pak、Jaime L. Mayo、Endrit Shurdha

  DOI：10.1016/j.tetlet.2005.10.147

  日期：2006.1

  4,4',5,5'-Tetraiododibenzo-24-crown-8 (9), a practical building block, was prepared under efficient and mild reaction conditions starting from the simple starting material, catechol (1). Highly conjugated 4,4',5,5'-tetraethynyldibenzo-24-crown-8 (10a,b) were prepared via a Sonogashira, coupling reaction from tetraiodocrown ether 9. These highly conjugated crown ethers form complexes in CD2Cl2 with dibenzylammonium hexafluorophosphate in a 1:1 ratio. Emission spectrum of pseudorotaxane 11 shows a dramatic shift from the non-complexed precursor. (c) 2005 Elsevier Ltd. All rights reserved.