1,5-bis(2-{2-[2-(azide)ethoxy]ethoxy}ethoxy)naphthalene | 1033920-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-bis(2-{2-[2-(azide)ethoxy]ethoxy}ethoxy)naphthalene
• 英文别名: 1,5-Bis[2-(2-azidoethoxy)ethoxy]naphthalene
• CAS: 1033920-85-2
• 化学式: C₁₈H₂₂N₆O₄
• 分子量: 386.41
• InChiKey: QPRMJLHBMUADGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11,12-二脱氢-Δ-氧代二苯并[B,F]氮杂环辛-5(6H)-戊酸 、 1,5-bis(2-{2-[2-(azide)ethoxy]ethoxy}ethoxy)naphthalene 以 乙腈 为溶剂， 反应 48.0h， 生成 5-[5-[2-[2-[5-[2-[2-[13-(4-Carboxybutanoyl)-3,4,5,13-tetrazatetracyclo[13.4.0.02,6.07,12]nonadeca-1(19),2(6),3,7,9,11,15,17-octaen-5-yl]ethoxy]ethoxy]naphthalen-1-yl]oxyethoxy]ethyl]-3,4,5,13-tetrazatetracyclo[13.4.0.02,6.07,12]nonadeca-1(19),2(6),3,7,9,11,15,17-octaen-13-yl]-5-oxopentanoic acid
  参考文献：
  名称：

  二苯并氮杂环辛炔作为[2]轮烷的反应性链终止剂

  摘要：

  通过应变促进的叠氮化物-炔烃环加成反应（SPAAC），引入了应变的二苯并氮杂环辛炔（DIBAC）衍生物来制备轮烷，也称为无铜点击反应。DIBAC可以有效地充当庞大的反应性链终止剂，以将由重氮官能化的二烷氧基萘客体和四阳离子环双（百草枯-对苯撑）（CBPQT 4+）主体组成的拟轮烷结构转化为相应的[2]轮烷。此外，已证明DIBAC的使用仅限于短的刚性大环化合物，因为它不能充当具有较大冠醚大环主体的轮烷的阻滞剂。

  DOI：

  10.1002/ejoc.201700305

文献信息

• Controlling Switching in Bistable [2]Catenanes by Combining Donor–Acceptor and Radical–Radical Interactions
  作者：Zhixue Zhu、Albert C. Fahrenbach、Hao Li、Jonathan C. Barnes、Zhichang Liu、Scott M. Dyar、Huacheng Zhang、Juying Lei、Raanan Carmieli、Amy A. Sarjeant、Charlotte L. Stern、Michael R. Wasielewski、J. Fraser Stoddart

  DOI：10.1021/ja3037355

  日期：2012.7.18

  achieving redox-active switching between two translational isomers, which are driven (i) by donor-acceptor interactions between the CBPQT(4+) ring and DNP, or (ii) radical-radical interactions between CBPQT(2(•+)) and BIPY(•+), respectively. The switching processes, as well as the nature of the donor-acceptor interactions in the ground states and the radical-radical interactions in the reduced states

  两个氧化还原活性双稳态 [2] 链烷由不同尺寸的大环聚醚组成，包含富电子 1,5-二氧萘 (DNP) 和缺电子 4,4'-联吡啶 (BIPY(2+)) 单元，机械互锁与四阳离子环芳环双（百草枯-对亚苯基）（CBPQT（4+）），通过供体-受体模板导向合成获得，采用铜（I）催化叠氮化物-炔烃最终机械键形成步骤中的 1,3-偶极环加成。这些双稳态 [2] 链证明了实现两种翻译异构体之间氧化还原活性切换的设计策略，其驱动 (i) 由 CBPQT(4+) 环和 DNP 之间的供体 - 受体相互作用，或 (ii) 自由基 - 自由基CBPQT(2(•+)) 和 BIPY(•+) 之间的相互作用，分别。通过单晶 X 射线晶体学、动态 (1) H NMR 光谱、循环分析研究了转换过程以及基态中供体-受体相互作用和还原态中自由基-自由基相互作用的性质。伏安法、紫外/可见光谱电化学和电子顺磁共振 (EPR)
• Relative Unidirectional Translation in an Artificial Molecular Assembly Fueled by Light
  作者：Hao Li、Chuyang Cheng、Paul R. McGonigal、Albert C. Fahrenbach、Marco Frasconi、Wei-Guang Liu、Zhixue Zhu、Yanli Zhao、Chenfeng Ke、Juying Lei、Ryan M. Young、Scott M. Dyar、Dick T. Co、Ying-Wei Yang、Youssry Y. Botros、William A. Goddard、Michael R. Wasielewski、R. Dean Astumian、J. Fraser Stoddart

  DOI：10.1021/ja4094204

  日期：2013.12.11

  Motor molecules present in nature convert energy inputs, such as a chemical fuel or incident photons of light, into directed motion and force biochemical systems away from thermal equilibrium. The ability not only to control relative movements of components in molecules but also to drive their components preferentially in one direction relative to each other using versatile stimuli is one of the keys to future technological applications. Herein, we describe a wholly synthetic small-molecule system that, under the influence of chemical reagents, electrical potential, or visible light, undergoes unidirectional relative translational motion. Altering the redox state of a cyclobis(paraquat-p-phenylene) ring simultaneously (i) inverts the relative heights of kinetic barriers presented by the two termini-one a neutral 2-isopropylphenyl group and the other a positively charged 3,5-dimethylpyridinium unit-of a constitutionally asymmetric dumbbell, which can impair the threading/dethreading of a [2]pseudorotaxane, and (ii) controls the ring's affinity for a 1,5-dioxynaphthalene binding site located in the dumbbell's central core. The formation and subsequent dissociation of the [2]pseudorotaxane by passage of the ring over the neutral and positively charged termini of the dumbbell component in one, and only one, direction relatively defined has been demonstrated by (i) spectroscopic (H-1 NMR and UV/vis) means and cyclic voltammetry as well as with (ii) DFT calculations and by (iii) comparison with control compounds in the shape of constitutionally symmetrical [2]pseudorotaxanes, one with two positively charged ends and the other with two neutral ends. The operation of the system relies solely on reversible, yet stable, noncovalent bonding interactions. Moreover, in the presence of a photosensitizer, visible-light energy is the only fuel source that is needed to drive the unidirectional molecular translation, making it feasible to repeat the operation numerous times. without the buildup of byproducts.