9,10-双(3-溴丙基)蒽 | 101543-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9,10-双(3-溴丙基)蒽
• 英文名称: 9,10-bis(3-bromopropyl)anthracene
• 英文别名: 9,10-bis-(3-bromo-propyl)-anthracene；9,10-Bis-(3-brom-propyl)-anthracen
• CAS: 101543-04-8
• 化学式: C₂₀H₂₀Br₂
• 分子量: 420.187
• InChiKey: QXZXJZPOCMAWGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  9,10-双(3-溴丙基)蒽 在 正丁基锂 、 四甲基乙二胺 、 cadmium(II) chloride 作用下， 生成 9,10-Bis-(3-anthracen-9-yl-propyl)-anthracene
  参考文献：
  名称：

  Fiedler, Juergen; Huber, Walter; Muellen, Klaus, Angewandte Chemie, 1986, vol. 98, # 5, p. 444 - 445

  摘要：

  DOI：
• 作为产物：
  描述：

  蒽-9,10-二锂 生成 9,10-双(3-溴丙基)蒽
  参考文献：
  名称：

  Fiedler, Juergen; Huber, Walter; Muellen, Klaus, Angewandte Chemie, 1986, vol. 98, # 5, p. 444 - 445

  摘要：

  DOI：

文献信息

• Study of cavity size and nature of bridging units on recognition of nucleotides by cyclophanes
  作者：Prakash P. Neelakandan、Paramjyothi C. Nandajan、Baby Subymol、Danaboyina Ramaiah

  DOI：10.1039/c0ob00673d

  日期：——

  We synthesized a few novel cyclophanes CP-1 to CP-4 containing anthracene units linked together through different bridging and spacer groups and have investigated their interactions with various nucleosides and nucleotides. Of these systems, CP-1 and CP-3 showed selectivity for 5′-GTP and 5′-ATP as compared to other nucleotides and nucleosides, whereas negligible selectivity was observed with CP-2 and CP-4. Interestingly, CP-1, CP-2 and CP-3 exhibited significant binding interactions with the fluorescent indicator, 8-hydroxy-1,3,6-pyrene trisulfonate (HPTS), resulting in the formation of non-fluorescent complexes. Titration of these complexes with nucleosides and nucleotides resulted in the displacement of HPTS, leading to the revival of its fluorescence intensity. It was observed that 5′-GTP induced the maximum displacement of HPTS from the complex [CP-1·HPTS] with an overall fluorescence enhancement of ca. 150-fold, while 5′-ATP induced ca. 45-fold. Although the displacement of HPTS from the complexes [CP-2·HPTS] and [CP-3·HPTS] was found to be similar to that of [CP-1·HPTS], these complexes showed lesser selectivity and sensitivity. In contrast, negligible displacement of HPTS was observed from the complex [CP-4·HPTS] under similar conditions. These results indicate that CP-1, having a well-defined cavity and good electron acceptor (viologen), is capable of forming selective and stable complexes. Though CP-2 and CP-3 retain the good electron acceptor (viologen), their reduced aromatic surface and larger cavity, respectively, resulted in lesser sensitivity. In contrast, CP-4 having a large cavity and a poor acceptor (1,2-bis(pyridin-4-yl)ethene) showed negligible selectivity, thereby indicating the importance of cavity size, bridging unit and aromatic surface on biomolecular recognition properties of cyclophanes.

  我们合成了一系列新型冠醚CP-1至CP-4，这些冠醚包含蒽单元，通过不同的桥连和间隔基团连接在一起，并研究了它们与各种核苷和核苷酸的相互作用。在这些系统中，CP-1和CP-3对5′-GTP和5′-ATP表现出选择性，而CP-2和CP-4的选择性则微乎其微。有趣的是，CP-1、CP-2和CP-3与荧光指示剂8-羟基-1,3,6-芘三磺酸盐（HPTS）表现出显著的结合相互作用，形成非荧光复合物。这些复合物与核苷和核苷酸的滴定导致HPTS的置换，从而恢复其荧光强度。观察到5′-GTP从复合物[CP-1·HPTS]中诱导出最大程度的HPTS置换，总体荧光增强约150倍，而5′-ATP则诱导约45倍。尽管从复合物[CP-2·HPTS]和[CP-3·HPTS]中HPTS的置换与[CP-1·HPTS]相似，但这些复合物表现出较低的选择性和敏感性。相比之下，在类似条件下，复合物[CP-4·HPTS]中HPTS的置换可以忽略不计。这些结果表明，CP-1具有良好的空腔和良好的电子受体（紫精），能够形成选择性和稳定的复合物。尽管CP-2和CP-3保留了好的电子受体（紫精），但它们的减少的芳香表面和较大的空腔分别导致了较低的敏感性。相比之下，CP-4具有较大的空腔和较差的受体（1,2-双（4-吡啶基）乙烯），表现出微乎其微的选择性，从而表明空腔大小、桥连单元和芳香表面在环芳烃的生物分子识别特性中的重要性。
• 84. The preparation of 9 : 10-di-(4-carboxybutyl)anthracene and related reactions
  作者：K. Jasper Clark

  DOI：10.1039/jr9570000463

  日期：——
• Fiedler, Juergen; Huber, Walter; Muellen, Klaus, Angewandte Chemie, 1986, vol. 98, # 5, p. 444 - 445
  作者：Fiedler, Juergen、Huber, Walter、Muellen, Klaus

  DOI：——

  日期：——