2,6,14-tribromotriptycene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6,14-tribromotriptycene
• 英文别名: 2,6,14-Tribromo-9,10-dihydro-9,10-[1,2]benzenoanthracene；4,11,17-tribromopentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),3,5,9(14),10,12,15(20),16,18-nonaene
• 化学式: C₂₀H₁₁Br₃
• 分子量: 491.019
• InChiKey: JLTMUKRBITYDEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,6,14-tribromotriptycene 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 3-[11,18-Bis(2-carboxyethynyl)-4-pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2(7),3,5,9(14),10,12,15(20),16,18-nonaenyl]prop-2-ynoic acid
  参考文献：
  名称：

  Triptycene based chemosensors for selective detection of mercury(II)/iron(III) in aqueous medium

  摘要：

  Synthesis and characterization of two trisubstituted triptycene derivatives in high yields are being reported. Aqueous solutions of sodium salt of 2,6,14-and 2,7,14-triptycenetripropiolic acids ( 1c and 2c) have shown high selectivity for Hg2+ and Fe3+ ions, through quenching of fluorescence intensity, when tested in presence of other metal ions in pure aqueous medium. In addition, pH dependence of fluorescence quenching has been studied. Binding stoichiometry between probes and metal ions ( Hg2+ and Fe3+) has been studied using Job's plot, and corresponding association constant has been evaluated. 1c and 2c are the unique examples of triptycene based tripods that act as chemosensors for selective detection of metal ions. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.01.025
• 作为产物：
  描述：

  三蝶烯 在 镍 氢溴酸 、 硝酸 、 一水合肼 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.33h， 生成 2,6,14-tribromotriptycene
  参考文献：
  名称：

  2,6,14-和2,7,14-三取代三茂烯衍生物的合成与结构

  摘要：

  高效合成了一系列2,6,14-和2,7,14-三取代的三并茂衍生物，并通过NMR，MS光谱和X射线分析确定了它们的结构。这些三取代三联体是构建新型受体和合成分子机器的潜在组成部分。

  DOI：

  10.1021/jo061067t

文献信息

• Desymmetrization Strategy to Achieve Triptycene‐Based 3,6‐Dimethoxytriphenylenes via Oxidative Cyclodehydrogenation
  作者：Dennis Reinhard、Frank Rominger、Michael Mastalerz

  DOI：10.1002/ejoc.202001073

  日期：2020.10.22

  high yield of 97 %, a less symmetric triptycene(C3v) is necessary as precursor for cyclodehydrogenative Scholl‐type oxidation, by taking into account the regioselectivity of the C‐C bond formation controlled by attached methoxy groups. In addition, Scholl‐type oxidations and photochemical reactions are compared.

  要实现高对称的三茂基六甲氧基三亚苯基，以97％的高收率，考虑到受C控制的C-C键形成的区域选择性，较低对称的三茂（C 3 v）作为环脱氢Scholl型氧化的前体是必需的。连接的甲氧基。此外，还比较了Scholl型氧化和光化学反应。
• Concentration dependent supramolecular interconversions of triptycene-based cubic, prismatic, and tetrahedral structures
  作者：Sourav Chakraborty、Kevin J. Endres、Ranajit Bera、Lukasz Wojtas、Charles N. Moorefield、Mary Jane Saunders、Neeladri Das、Chrys Wesdemiotis、George R. Newkome

  DOI：10.1039/c7dt04571a

  日期：——

  The quantitative, single step, self-assembly of a shape-persistent, three-dimensional C3v-symmetric, triptycene-based tris-terpyridinyl ligand initially gives a platonic-based cubic architecture, which was unequivocally characterized by 1D and 2D NMR spectroscopy, mass spectrometry, and single crystal X-ray structural analysis. The unique metal–ligand binding properties of the Cd2+ analogue of this

  形状持久的三维C 3 v对称，三并茂基的三-叔吡啶基配体的定量，单一步骤的自组装最初提供了基于柏拉图的立方结构，该结构通过1D和2D NMR光谱明确表征，质谱和单晶X射线结构分析。这种结构的Cd 2+类似物独特的金属-配体结合特性在立方体，棱柱形和四面体形结构之间产生了浓度依赖性的动态平衡。稀释通过稳定的棱柱状中间体将这个立方转化为两个相同的四面体。增加浓度会逆转这一过程。
• Triptycene based chemosensors for selective detection of mercury(II)/iron(III) in aqueous medium
  作者：Sourav Chakraborty、Snehasish Mondal、Neeladri Das

  DOI：10.1016/j.ica.2014.01.025

  日期：2014.3

  Synthesis and characterization of two trisubstituted triptycene derivatives in high yields are being reported. Aqueous solutions of sodium salt of 2,6,14-and 2,7,14-triptycenetripropiolic acids ( 1c and 2c) have shown high selectivity for Hg2+ and Fe3+ ions, through quenching of fluorescence intensity, when tested in presence of other metal ions in pure aqueous medium. In addition, pH dependence of fluorescence quenching has been studied. Binding stoichiometry between probes and metal ions ( Hg2+ and Fe3+) has been studied using Job's plot, and corresponding association constant has been evaluated. 1c and 2c are the unique examples of triptycene based tripods that act as chemosensors for selective detection of metal ions. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis and Structure of 2,6,14- and 2,7,14-Trisubstituted Triptycene Derivatives
  作者：Chun Zhang、Chuan-Feng Chen

  DOI：10.1021/jo061067t

  日期：2006.8.1

  A series of 2,6,14- and 2,7,14-trisubstituted triptycene derivatives were efficiently synthesized and their structures were determined by NMR, MS spectra, and X-ray analysis. These trisubstituted triptycenes are potential building blocks for constructing novel receptors and synthetic molecular machines.

  高效合成了一系列2,6,14-和2,7,14-三取代的三并茂衍生物，并通过NMR，MS光谱和X射线分析确定了它们的结构。这些三取代三联体是构建新型受体和合成分子机器的潜在组成部分。