4,4''-bis(bromomethyl)-p-terphenyl | 41425-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4''-bis(bromomethyl)-p-terphenyl
• 英文别名: 1,1':4',1''-Terphenyl, 4,4''-bis(bromomethyl)-；1,4-bis[4-(bromomethyl)phenyl]benzene
• CAS: 41425-57-4
• 化学式: C₂₀H₁₆Br₂
• 分子量: 416.155
• InChiKey: PICNGHXGHHKZLO-UHFFFAOYSA-N

物化性质

• 沸点：
  516.4±50.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• 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：

  4,4''-bis(bromomethyl)-p-terphenyl 在 硫酸 、 硝酸 、 二氧化氮 作用下， 生成 2,2',2''-Trinitro-p-terphenyl-4,4''-dicarbaldehyd
  参考文献：
  名称：

  Wulff,G. et al., Chemische Berichte, 1979, vol. 112, p. 2854 - 2865

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4''-二甲基-1,1':4',1''-三联苯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 2.5h， 以40%的产率得到4,4''-bis(bromomethyl)-p-terphenyl
  参考文献：
  名称：

  [C−H···O] Interactions as a Control Element in Supramolecular Complexes:  Experimental and Theoretical Evaluation of Receptor Affinities for the Binding of Bipyridinium-Based Guests by Catenated Hosts¹

  摘要：

  Macrocyclic receptors incorporating two facing pi-electron-rich aromatic surfaces, held at a distance of approximately 7 Angstrom by polyether spacers, bind bipyridinium-based guests. This recognition motif, which is dictated by pi-pi stacking and [C-H ... O] hydrogen-bonding interactions, has led to the development of efficient template-directed syntheses of mechanically interlocked molecules, such as catenanes and rotaxanes. By employing a supramolecularly assisted synthetic methodology based on these interactions, we have self-assembled two novel [3]catenanes, each incorporating two 1,5-dioxynaphtho-38-crown-10 components and one bipyridinium-based tetracationic cyclophane component. Single-crystal X-ray analyses of these [3]catenanes revealed that they possess internal cavities bounded on two opposite sites by pi-electron-rich 15-dioxynaphthalene units separated by a distance of approximately 7-8 Angstrom. Despite the presence of apparently ideal "binding pockets", these mechanically interlocked compounds steadfastly refuse to bind bipyridinium-based guests in solution, as demonstrated by both H-1 NMR and UV-vis spectroscopy. AMBER* and HF/3-21G calculations on appropriate models show that the absence of [C-H ... O] hydrogen-bonding interactions is responsible for the instability of these geometrically ideal complexes. The [C-H ... O] bond appears to be quantitatively much more important than pi-pi stacking interactions in these particular systems.

  DOI：

  10.1021/ja982748b

文献信息

• Electron transfer in bis-porphyrin donor-acceptor compounds with polyphenylene spacers shows a weak distance dependence
  作者：Anna Helms、David Heiler、George McLendon

  DOI：10.1021/ja00041a047

  日期：1992.7

  containing one, two, or three phenyl bridges. Complete synthetic details are provided. For studies of photochemical electron transfer, mixed metals were incorporated, with zinc in one porphyrin macrocycle and Fe III (bis-imidazole) in the other macrocycle. When photoexcited, an electron is transferred from Zn to Fe III

  已经合成了一系列亚苯基桥连的双卟啉加合物，包含一个、两个或三个苯桥。提供了完整的合成细节。为了研究光化学电子转移，加入了混合金属，锌在一个卟啉大环中，而 Fe III（双咪唑）在另一个大环中。当光激发时，一个电子从 Zn 转移到 Fe III
• Synthesis, Molecular Modeling, and K⁺ Channel-Blocking Activity of Dequalinium Analogues Having Semirigid Linkers
  作者：Joaquin Campos Rosa、Dimitrios Galanakis、C. Robin Ganellin、Philip M. Dunn

  DOI：10.1021/jm950884a

  日期：1996.1.1

  Dequalinium [1,1'-(decane-1, 10-diyl)bis(2-methyl-4-aminoquinolinium)] is an effective blocker of the small conductance Ca2(+)-activated K+ channel. It has been shown that the number of methylene groups in the alkyl chain linking the two quinolinium rings of this type of molecule is not critical for activity. To further investigate the role of the linker, analogues of dequalinium have been synthesized

  角鲨烯[1,1'-（癸烷-1，10-二基）双（2-甲基-4-氨基喹啉）]是小电导Ca2（+）激活的K +通道的有效阻滞剂。已经表明，在连接这种类型的分子的两个喹啉鎓环的烷基链中的亚甲基的数目对于活性不是关键的。为了进一步研究接头的作用，已合成了癸胺盐的类似物，其中烷基链已被CH2XCH2取代，其中X是含有芳香环的刚性或半刚性基团。已经测试了该化合物对大鼠交感神经元缓慢的超极化后的阻滞作用。最有效的化合物为X =菲基，芴基，顺二苯乙烯和C6H4（CH2）nC6H4，其中n = 0-4。使用XED / COSMIC分子建模系统研究了化合物的构象偏好。尽管类似物的效力对接头（X）的构象性质有一定的依赖性，但是总体上，具有实质性结构差异的X基团是可容忍的。X似乎为两个喹啉基团提供了支持，并且不直接与通道相互作用。刚性基团X提供的喹啉鎓环之间的分子内间隔对于活性不是关键。这可能归因于杂环的残留构象迁
• Bis(7)-tacrine Derivatives as Multitarget-Directed Ligands: Focus on Anticholinesterase and Antiamyloid Activities
  作者：Maria Laura Bolognesi、Manuela Bartolini、Francesca Mancini、Gianpaolo Chiriano、Luisa Ceccarini、Michela Rosini、Andrea Milelli、Vincenzo Tumiatti、Vincenza Andrisano、Carlo Melchiorre

  DOI：10.1002/cmdc.201000086

  日期：——

  this strategy, we developed a series of dimeric ligands derived from the lead candidate bis(7)‐tacrine (1), for which a multifunctional profile has been disclosed. These derivatives were evaluated at validated targets, namely cholinesterases and amyloid production and aggregation. Compound 3 resulted more effective than 1 in inhibiting BACE‐1 activity and amyloid self‐aggregation.

  多靶点药物发现是设计用于治疗阿尔茨海默氏病的新药物的新兴方法。使用这种策略，我们开发了一系列衍生自主要候选物质bis（7）-他克林（1）的二聚体配体，针对该配体已披露了其多功能性。在验证的目标即胆碱酯酶和淀粉样蛋白的产生和聚集中评估了这些衍生物。化合物3在抑制BACE-1活性和淀粉样蛋白自聚集方面比1种更有效。
• Controlled Self-Assembly and Multistimuli-Responsive Interconversions of Three Conjoined Twin-Cages
  作者：Li-Xuan Cai、Dan-Ni Yan、Pei-Ming Cheng、Jin-Jin Xuan、Shao-Chuan Li、Li-Peng Zhou、Chong-Bin Tian、Qing-Fu Sun

  DOI：10.1021/jacs.0c12064

  日期：2021.2.3

  palladium corners and a new bis-bidentate ligand (1). While cage 2 features three mechanically coupled cavities, cages 3 and 4 are topologically isomeric helicate-based twin-cages based on the same metal/ligand stoichiometry. Sole formation of cage 2 or a dynamic mixture of cages 3 and 4 can be controlled by changing the solvents employed during the self-assembly. Structural conversions between cages 3

  离散配位超分子结构之间的刺激响应结构转换不仅对于构建智能功能材料至关重要，而且还提供了一个多功能的分子级平台来模拟生物转化过程。我们在此报告了三个拓扑学上前所未有的连体双笼的受控自组装，即一个订书钉互锁 Pd12L6 笼（2）和两个螺旋异构 Pd6L3 笼（3 和 4）由相同的顺式封闭钯角和一个新的双二齿配体 (1)。虽然笼 2 具有三个机械耦合腔，但笼 3 和 4 是基于相同金属/配体化学计量的拓扑异构螺旋基双笼。笼子 2 的单独形成或笼子 3 和 4 的动态混合物可以通过改变自组装过程中使用的溶剂来控制。笼子 3 和笼子 4 之间的结构转换可以由温度/溶剂和诱导适合的客体封装的变化触发。这种拓扑复杂的上层结构之间控制良好的相互转换可以为在可切换系统内实现各种功能奠定坚实的基础。
• Self‐Assembly of an [M₈L2₄]¹⁶⁺ Intertwined Cube and a Giant [M₁₂L1₆]²⁴⁺ Orthobicupola
  作者：Arppitha Baby Sainaba、Mangili Venkateswarulu、Pallab Bhandari、Jack K. Clegg、Partha Sarathi Mukherjee

  DOI：10.1002/anie.202315572

  日期：2024.1.2

  Through coordination‐driven self‐assembly, aesthetically captivating structures can be formed by tuning the length or flexibility of various components. The self‐assembly of an elongated rigid terphenyl‐based tetra‐pyridyl ligand (L1) with a cis‐Pd(II) acceptor produces an [M₁₂L1₆]²⁴⁺ triangular orthobicupola structure (1). When flexibility is introduced into the ligand by the incorporation of a ‐CH₂‐ group between the dipyridylamine and terphenyl rings in the ligand (L2), anunique [M₈L2₄]¹⁶⁺ water‐soluble ‘intertwined cubic structure’ (2) results. The inherent flexibility of ligand L2 might be the key factor behind the formation of the thermodynamically stable and ′intertwined cubic structure′ in this scenario. This research showcases the ability to design and fabricate novel, topologically distinctive molecular structures by a straightforward and efficient approach.

  摘要通过配位驱动的自组装，可以调整各种成分的长度或柔性，形成美观迷人的结构。拉长的刚性三联苯基四吡啶配体（L1）与顺式钯（II）受体的自组装产生了[M12L16]24+ 三角形正交乌托邦结构（1）。如果在配体（L2）的二吡啶基胺环和三联苯环之间加入一个-CH2-基团，为配体引入灵活性，则会产生独特的[M8L24]16+水溶性 "交织立方结构"（2）。在这种情况下，配体 L2 固有的灵活性可能是形成热力学稳定的 "交织立方结构 "的关键因素。这项研究展示了通过直接高效的方法设计和制造新颖的、拓扑结构独特的分子结构的能力。