18,21,24-Trioxa-3,11,33-triazatetracyclo[24.2.2.213,16.15,9]tritriaconta-1(29),5(33),6,8,13,15,26(30),27,31-nonaene-4,10-dione | 954407-13-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 18,21,24-Trioxa-3,11,33-triazatetracyclo[24.2.2.213,16.15,9]tritriaconta-1(29),5(33),6,8,13,15,26(30),27,31-nonaene-4,10-dione
• 英文别名: 18,21,24-trioxa-3,11,33-triazatetracyclo[24.2.2.213,16.15,9]tritriaconta-1(29),5(33),6,8,13,15,26(30),27,31-nonaene-4,10-dione
• CAS: 954407-13-7
• 化学式: C₂₇H₂₉N₃O₅
• 分子量: 475.544
• InChiKey: PUKZMNZQSPOOSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  35
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  18,21,24-Trioxa-3,11,33-triazatetracyclo[24.2.2.213,16.15,9]tritriaconta-1(29),5(33),6,8,13,15,26(30),27,31-nonaene-4,10-dione 、 N-(4-(4-azidophenethyl)phenyl)-3,5-dimethylbenzamide 以 氘代氯仿 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Low Temperature Capture of Pseudorotaxanes

  摘要：

  Yields of a rotaxane can be improved by employing a two-step capture protocol. Cooling a solution of the linear and macrocyclic components required for the rotaxane increases the population of the target pseudorotaxane, which is then captured by a rapid capping reaction between an azide and PPh3. The resulting iminophosphorane rotaxane can then be manipulated synthetically at elevated temperatures.

  DOI：

  10.1021/ol1027915
• 作为产物：
  描述：

  吡啶-2.6-二羧酸二甲酯 、 [4-[2-[2-[[4-(Aminomethyl)phenyl]methoxy]ethoxy]ethoxymethyl]phenyl]methanamine 以 甲醇 为溶剂， 反应 144.0h， 以0.11 g的产率得到18,21,24-Trioxa-3,11,33-triazatetracyclo[24.2.2.213,16.15,9]tritriaconta-1(29),5(33),6,8,13,15,26(30),27,31-nonaene-4,10-dione
  参考文献：
  名称：

  使用乙酸根阴离子在中性尿素基分子开关中诱导翻译异构化。

  摘要：

  DOI：

  10.1002/anie.200702197

文献信息

• Acid/Base- and Anion-Controllable Organogels Formed From a Urea-Based Molecular Switch
  作者：Sheng-Yao Hsueh、Chun-Ting Kuo、Tsan-Wen Lu、Chien-Chen Lai、Yi-Hung Liu、Hsiu-Fu Hsu、Shie-Ming Peng、Chun-hsien Chen、Sheng-Hsien Chiu

  DOI：10.1002/anie.201004090

  日期：2010.11.22

  A switch in time: Gel–sol transitions of a urea‐based [2]rotaxane gelator are controlled by the degree of solvent exposure of the hydrogen‐bond‐donating urea station and the orientation of the hydrogen‐bond‐accepting CO groups of the interlocked ethylene glycol based macrocycle (N blue, O and macrocycle red, phenyl green). Both acid/base and anion‐exchange control can be used to reversibly transition

  时间上的转换：脲基[2]轮烷胶凝剂的凝胶-溶胶转变是由给氢键的尿素站的溶剂暴露程度和接受氢键的CO基团的方向控制的互锁的乙二醇基大环化合物（N蓝色，O和大环红色，苯基绿色）。酸/碱和阴离子交换控制均可用于在溶液状态和凝胶状态之间可逆地将轮烷中的1-戊醇转化。
• A Phosphine Oxide Functional Group Based [2]Rotaxane That Operates as a Multistable Molecular Shuttle
  作者：Ming Cheng、Li Liu、Yihan Cao、Juli Jiang、Leyong Wang

  DOI：10.1002/cphc.201501016

  日期：2016.6.17

  pyridinediamide crown ether macrocycle and a thread bearing phosphine oxide, urea, and dibenzylammonium functional groups was successfully developed and characterized by 1H NMR and 2D NMR spectroscopy, mass spectrometry, and single‐crystal analysis. The three recognition sites in the [2]rotaxane were sorted from strong to weak, according to their bonding abilities, so that the macrocycle could move along

  基于吡啶二酰胺冠醚大环和带有氧化膦，尿素和二苄基铵官能团的线的可切换[2]轮烷已成功开发并通过1 H NMR和2D NMR光谱，质谱和单晶分析进行了表征。[2]轮烷中的三个识别位点根据其键合能力从强到弱排序，因此大环可以沿着线从一侧到另一侧以定向方式移动，作为多稳态分子穿梭。
• Integrating replication processes with mechanically interlocked molecular architectures
  作者：Annick Vidonne、Douglas Philp

  DOI：10.1016/j.tet.2008.05.049

  日期：2008.9

  A kinetic model for the integration of self-replication with the formation of a mechanically interlocked molecular architecture, namely a rotaxane, is presented. The logical steps required to convert this model into molecular structures through consideration of the design criteria highlighted by the model are discussed and executed. Ultimately, despite careful design, the rotaxane synthesised did not replicate as expected. The reasons for this failure are traced by experiment and computation to the sub-optimal association constant for the pseudorotaxane complex required to form the replicating rotaxane. Additionally, a deleterious supramolecular steric effect, operating through the proximity of the macrocyclic component of the pseudorotaxane to the transition state for the stoppering reaction is identified computationally. (C) 2008 Elsevier Ltd. All rights reserved.
• Orthogonal Recognition Processes Drive the Assembly and Replication of a [2]Rotaxane
  作者：Tamara Kosikova、Nurul Izzaty Hassan、David B. Cordes、Alexandra M. Z. Slawin、Douglas Philp

  DOI：10.1021/jacs.5b09738

  日期：2015.12.30

  Within a small, interconnected reaction network, orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. Rotaxane formation is governed by a central, hydrogen-bonding-mediated binding equilibrium between a macrocycle and a linear component, which associate to give a reactive pseudorotaxane. Both the pseudorotaxane and the linear component undergo irreversible, recognition-mediated 1,3-dipolar cycloaddition reactions with a stoppering maleimide group, forming rotaxane and thread, respectively. As a result of these orthogonal recognition-mediated processes, the rotaxane and thread can act as auto-catalytic templates for their own formation and also operate as cross-catalytic templates for each other. However, the interplay between the recognition and reaction processes in this reaction network results in the formation of undesirable pseudorotaxane complexes, causing thread formation to exceed rotaxane formation in the current experimental system. Nevertheless, in the absence of competitive macrocyde-binding sites, realization of a replicating network favoring formation of rotaxane is possible.
• Two [2]pseudorotaxane-like complexes and their corresponding [2]rotaxanes stabilized via interactions on opposite ends of the same macrocycle
  作者：Wei-Chung Hung、Liang-Yun Wang、Chien-Chen Lai、Yi-Hung Liu、Shie-Ming Peng、Sheng-Hsien Chiu

  DOI：10.1016/j.tetlet.2008.10.153

  日期：2009.1

  A multiple-use macrocycle recognizes dibenzylammonium ions and 2,6-lutidine derivatives, each in a [2]pseudorotaxane-like manner, through interactions with its diethylene glycol (hydrogen bonding) and 2,6-pyridinedicarboxamide (Pd2+ chelation) spacers, respectively. We characterized these complexes in the solid state (X-ray crystallography) and in solution (H-1 NMR spectroscopy). The synthesis of two corresponding [2]rotaxanes confirmed that these recognition systems possess [2]pseudorotaxane geometries in solution. (C) 2008 Elsevier Ltd. All rights reserved.