5,6'-dibromo-5'-methyl-[2,3']bipyridine | 1175709-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,6'-dibromo-5'-methyl-[2,3']bipyridine
• 英文别名: 2-bromo-5-(5-bromopyridin-2-yl)-3-methylpyridine
• CAS: 1175709-61-1
• 化学式: C₁₁H₈Br₂N₂
• 分子量: 328.006
• InChiKey: VABYGKRRNBNCRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6'-dibromo-5'-methyl-[2,3']bipyridine 在 乙酰氯 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以89%的产率得到5-bromo-6'-iodo-5'-methyl-[2,3']bipyridine
  参考文献：
  名称：

  Synthesis of dihalo bi- and terpyridines by regioselective Suzuki–Miyaura cross-coupling reactions

  摘要：

  This paper describes ail efficient and regioselective synthetic route leading to new dihalobi- and terpyridines. We developed a strategy based on regioselective sequence of Suzuki-Miyaura cross-coupling reactions between bromopyridyl boronic acids and dihalopyridines and dihalobipyridines. The study of the influence of the nature and the position of the halogen atoms leads to prepare bromoiododerivatives to obtain good selectivities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.049
• 作为产物：
  描述：

  2,5-二溴吡啶 、 6-溴-5-甲基吡啶-3-硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以9%的产率得到5,6'-dibromo-5'-methyl-[2,3']bipyridine
  参考文献：
  名称：

  Synthesis of dihalo bi- and terpyridines by regioselective Suzuki–Miyaura cross-coupling reactions

  摘要：

  This paper describes ail efficient and regioselective synthetic route leading to new dihalobi- and terpyridines. We developed a strategy based on regioselective sequence of Suzuki-Miyaura cross-coupling reactions between bromopyridyl boronic acids and dihalopyridines and dihalobipyridines. The study of the influence of the nature and the position of the halogen atoms leads to prepare bromoiododerivatives to obtain good selectivities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.049

文献信息

• Aromatic garlands, as new foldamers, to mimic protein secondary structure
  作者：Anne Sophie Voisin-Chiret、Grégory Burzicki、Serge Perato、Marcella De Giorgi、Carlo Franchini、Jana Sopková-de Oliveira Santos、Sylvain Rault

  DOI：10.1016/j.tet.2012.02.035

  日期：2012.6

  secondary structural elements such as helices, turns, and sheets. Many of these functions are affected by a small number of key structural element, protein–protein interactions. Their mimicry by peptide and non-peptide scaffolds has become a major focus of contemporary research. This paper examines oligomeric system as new foldamers, which either reproduce the local topography of the helix, or project

  蛋白质调节所有生物功能的大部分，并且由高度组织化的二级结构元素（例如，螺旋，弯角和薄片）组成。这些功能中的许多功能都受到少数关键结构元素（蛋白质与蛋白质的相互作用）的影响。通过肽和非肽支架模仿它们已成为当代研究的主要焦点。本文将寡聚体系统视为新的折叠子，它们可以复制螺旋的局部形貌，或以类似于α-螺旋残基的方式投射适当的功能。
• Structural Characterizations of Oligopyridyl Foldamers, α-Helix Mimetics
  作者：Jana Sopkova-de Oliveira Santos、Anne Sophie Voisin-Chiret、Gregory Burzicki、Laure Sebaoun、Muriel Sebban、Jean-François Lohier、Rémi Legay、Hassan Oulyadi、Ronan Bureau、Sylvain Rault

  DOI：10.1021/ci200424a

  日期：2012.2.27

  Protein-protein interactions are central to many biological processes, from intracellular communication to cytoskeleton assembly, and therefore represent an important class of targets for new therapeutics. The most common secondary structure in natural proteins is an alpha-helix. Small molecules seem to be attractive candidates for stabilizing or disrupting protein protein interactions based on alpha-helices. In our study, we assessed the ability of oligopyridyl scaffolds to mimic the alpha-helical twist. The theoretical as well as experimental studies (X-ray diffraction and NMR) on conformations of bipyridines in the function of substituent and pyridine nitrogen positions were carried out. Furthermore, the experimental techniques showed that the conformations observed in bipyridines are maintained within a longer oligopyridyl scaffold (quaterpyridines). The alignment of the synthesized quaterpyridine with two methyl substituents showed that it is an alpha-helix foldamer; their methyl groups overlap very well with side chain positions, i and i + 3, of an ideal alpha-helix.