(±)-2,8-bis(2-bromoethoxy)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine | 1624286-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (±)-2,8-bis(2-bromoethoxy)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine
• 英文别名: 2,8-bis(2-bromoethoxy)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine；5,13-Bis(2-bromoethoxy)-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene；5,13-bis(2-bromoethoxy)-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene
• CAS: 1624286-09-4
• 化学式: C₁₉H₂₀Br₂N₂O₂
• 分子量: 468.188
• InChiKey: IMCOREGSWMABLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  625.3±55.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-2,8-bis(2-bromoethoxy)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine 在 potassium carbonate 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 29.0h， 生成 (±)-2,8-bis(2-(1H-imidazol-1-yl)ethoxy)-N,N-dimethyl-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocin-13-amine
  参考文献：
  名称：

  Discovery of Tröger's base analogues as selective inhibitors against human breast cancer cell line: Design, synthesis and cytotoxic evaluation

  摘要：

  A library of structurally diverse Troger's base analogues has been constructed via unusual amination of methylene bridge employing Vilsmeier-Haack conditions as well as by the incorporation of five and six membered heterocycles on the aromatic core of Troger's base framework. The constructed structurally diverse frameworks were evaluated for their cytotoxic activities against a panel of three human cancer lines A549 (lung adenocarcinoma), MDAMB-231 (breast) and SK-N-SH (neuroblastoma). From the activity profile obtained, a redesign of Troger's base analogues led to the construction of more potent molecular entities. The study led to development of a series of compounds with MDAMB-231 cell line specific cytotoxicity. Of the 30 compounds synthesized and evaluated, 7 compounds were found to possess cytotoxicity that is equivalent or better than standard drug doxorubicin against MDAMB-231 cell line while only one compound was found to be active against SK-N-SH cell line. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.044
• 作为产物：
  描述：

  对硝基苯酚 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 生成 (±)-2,8-bis(2-bromoethoxy)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine
  参考文献：
  名称：

  Troger碱基对位受体的设计与合成：宿主与客体的相互作用，是一项理论与实验相结合的研究。

  摘要：

  设计并合成了结合单氮杂冠醚的两种柔性Troger碱基对位受体C4TB和C5TB，用于双铵离子络合。通过（1）H NMR光谱学和DFT计算建立了宿主-客体相互作用的综合研究。具有较短烷基链间隔基的氯化双铵（A1）对受体的亲和力最高。使用M06-2X / cc-pVTZ计算（包括溶剂对客体-客体复合物的影响）来解释和合理化实验趋势。在1.71-1.98 A范围内观察到的较短的NH ... O或NH ... N氢键距离表明，在主体与客体之间存在强电荷辅助的氢键。（1）H NMR滴定中A5的异常行为（较高的结合常数）可追溯到客体的构象折叠。

  DOI：

  10.1039/c4ob02266a

文献信息

• Tröger's Base‐Based Cuboid Constructed by Chiral Self‐Discrimination
  作者：Conghao Shi、Pengbo Niu、Wang Xie、Jianmin Jiao、Yumei Li、Ranran Wang、Chen Lin、Leyong Wang、Juli Jiang

  DOI：10.1002/chem.202300410

  日期：2023.6.22

  Cuboid, a basic geometric structure, has been widely applied in architecture and mathematics. In chemistry, the introduction of cuboid structures always provides a specific structural shape, enhances the stability of the structure and improves the performance of materials. Herein, a simple strategy exploiting self‐discrimination to construct a cuboid‐stacking crystal material is proposed, in which a chiral macrocycle (TBBP) based on Tröger's base (TB) and benzophenone (BP) was synthesized as the building element of the cuboid. The cuboid is designed to be transformable compared with cuboid structures in previous work. For this reason, it is considered that the cuboid‐stacking structure can be transformed through external stimulation. Iodine vapor is selected as the external stimulus to transform the cuboid‐stacking structure due to the favorable interaction between iodine and the cuboid. The changes in the stacking mode of TBBP is studied by single‐crystal X‐ray diffraction (SCXRD) and powder X‐ray diffraction (PXRD). To our surprise, this Tröger's base‐based cuboid shows strong iodine adsorption capacity up to 3.43 g g⁻¹ and exhibits potential as a crystal material for iodine adsorption.

  摘要 长方体作为一种基本的几何结构，已被广泛应用于建筑和数学领域。在化学中，引入立方体结构总能提供特定的结构形状，增强结构的稳定性，提高材料的性能。本文提出了一种利用自分辨构建立方体堆叠晶体材料的简单策略，即合成一种基于特罗格碱（TB）和二苯甲酮（BP）的手性大循环（TBBP）作为立方体的构建元素。与以往工作中的立方体结构相比，该立方体的设计具有可转换性。因此，我们认为立方体堆叠结构可以通过外部刺激进行转化。由于碘与长方体之间存在良好的相互作用，因此选择碘蒸气作为外部刺激来改变长方体堆积结构。通过单晶 X 射线衍射（SCXRD）和粉末 X 射线衍射（PXRD）研究了 TBBP 堆积模式的变化。令我们惊讶的是，这种基于特罗格碱的立方体显示出强大的碘吸附能力，最高可达 3.43 g g-1，具有作为碘吸附晶体材料的潜力。
• Discovery of Tröger's base analogues as selective inhibitors against human breast cancer cell line: Design, synthesis and cytotoxic evaluation
  作者：Bhaskar Reddy Manda、Manjula Alla、Roopa Jones Ganji、Anthony Addlagatta

  DOI：10.1016/j.ejmech.2014.08.044

  日期：2014.10

  A library of structurally diverse Troger's base analogues has been constructed via unusual amination of methylene bridge employing Vilsmeier-Haack conditions as well as by the incorporation of five and six membered heterocycles on the aromatic core of Troger's base framework. The constructed structurally diverse frameworks were evaluated for their cytotoxic activities against a panel of three human cancer lines A549 (lung adenocarcinoma), MDAMB-231 (breast) and SK-N-SH (neuroblastoma). From the activity profile obtained, a redesign of Troger's base analogues led to the construction of more potent molecular entities. The study led to development of a series of compounds with MDAMB-231 cell line specific cytotoxicity. Of the 30 compounds synthesized and evaluated, 7 compounds were found to possess cytotoxicity that is equivalent or better than standard drug doxorubicin against MDAMB-231 cell line while only one compound was found to be active against SK-N-SH cell line. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Design and synthesis of Tröger's base ditopic receptors: host–guest interactions, a combined theoretical and experimental study
  作者：Manda Bhaskar Reddy、Myadaraboina Shailaja、Alla Manjula、Joseph Richard Premkumar、Garikapati Narahari Sastry、Katukuri Sirisha、Akella Venkata Subrahmanya Sarma

  DOI：10.1039/c4ob02266a

  日期：——

  Two flexible Troger's base ditopic receptors C4TB and C5TB incorporating monoaza crown ether were designed and synthesized for bisammonium ion complexation. A comprehensive study of host-guest interactions was established by (1)H NMR spectroscopy and DFT calculations. Bisammonium chloride (A1) with a shorter alkyl chain spacer showed the highest affinity for the receptors. M06-2X/cc-pVTZ calculations

  设计并合成了结合单氮杂冠醚的两种柔性Troger碱基对位受体C4TB和C5TB，用于双铵离子络合。通过（1）H NMR光谱学和DFT计算建立了宿主-客体相互作用的综合研究。具有较短烷基链间隔基的氯化双铵（A1）对受体的亲和力最高。使用M06-2X / cc-pVTZ计算（包括溶剂对客体-客体复合物的影响）来解释和合理化实验趋势。在1.71-1.98 A范围内观察到的较短的NH ... O或NH ... N氢键距离表明，在主体与客体之间存在强电荷辅助的氢键。（1）H NMR滴定中A5的异常行为（较高的结合常数）可追溯到客体的构象折叠。