5-azidomethyl-5'-methyl-2,2'-bipyridine | 455258-58-9

• 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-azidomethyl-5'-methyl-2,2'-bipyridine
• 英文别名: 2-[5-(Azidomethyl)pyridin-2-yl]-5-methylpyridine；2-[5-(azidomethyl)pyridin-2-yl]-5-methylpyridine
• CAS: 455258-58-9
• 化学式: C₁₂H₁₁N₅
• 分子量: 225.253
• InChiKey: BMGFZEVFVOCLLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-azidomethyl-5'-methyl-2,2'-bipyridine 在 indium 、 氯化铵 作用下， 以 乙醇 为溶剂， 以84%的产率得到5-aminomethyl-5'-methyl-2,2'-bipyridine
  参考文献：
  名称：

  Heptakis-6-(5-methylene-thioureido-5′-methyl-2,2′-bipyridyl)-β-cyclodextrin: synthesis and metal complexation study

  摘要：

  A new heptapode heptakis-6-(5-methylene-thioureido-5'-methyl-2,2'-bipyridyl)-beta-cyclodextrin was prepared and its complexation properties towards metal cations were investigated. Substituting the urea functions by the corresponding thioureas promoted the inversion of the metal coordination selectivity. Preliminary results showed the heptapode unable to complex lanthanides but authorise selective complexation of 'soft' and 'borderline' metal cations. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00071-6
• 作为产物：
  描述：

  5 5'-二甲基-2,2'-二吡啶 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 反应 3.5h， 生成 5-azidomethyl-5'-methyl-2,2'-bipyridine
  参考文献：
  名称：

  New Scaffolds for Supramolecular Chemistry: Upper-Rim Fully Tethered 5-Methyleneureido-5′-methyl-2,2′-bipyridyl Cyclodextrins

  摘要：

  Seven upper-rim fully tethered cyclodextrins (URFT-CDs) have been synthesised in a good average coupling yield using the one-step "phosphine imide" approach and their metal complexation behaviour with lanthanides and transition metals was explored. We observed that the A-TE-E light conversion process (antennae effect) occurs in the URFT-CD lanthanide complexes. A molecular re ox switch based on the corresponding iron complexes is also reported. A reversible intramolecular translocation of the Fe-II and Fe-III ions, between two distinct binding cavities has been monitored spectroscopically and achieved by chemical triggering, Finally, a negative allosteric control of ion recognition through the formation of a CD pseudocryptand is discussed.

  DOI：

  10.1002/1521-3765(20020603)8:11<2438::aid-chem2438>3.0.co;2-a

文献信息

• Construction and structure studies of DNA-bipyridine complexes as versatile scaffolds for site-specific incorporation of metal ions into DNA
  作者：Rui Wang、Srivathsan V. Ranganathan、Phensinee Haruehanroengra、Song Mao、Matteo Scalabrin、Daniele Fabris、Alan Chen、Hehua Liu、Abdalla E.A. Hassan、Jianhua Gan、Jia Sheng

  DOI：10.1080/07391102.2018.1441071

  日期：2019.2.11

  The facile construction of metal-DNA complexes using 'Click' reactions is reported here. A series of 2'-propargyl-modified DNA oligonucleotides were initially synthesized as structure scaffolds and were then modified through 'Click' reaction to incorporate a bipyridine ligand equipped with an azido group. These metal chelating ligands can be placed in the DNA context in site-specific fashion to provide

  本文报道了使用“点击”反应的金属-DNA复合物的简便构建。最初将一系列2'-炔丙基修饰的DNA寡核苷酸合成为结构支架，然后通过“点击”反应进行修饰，以掺入配备有叠氮基的联吡啶配体。可将这些金属螯合配体以位点特异性方式置于DNA环境中，以提供用于结合各种金属离子的通用模板，这些模板可使用简单的EDTA洗涤和过滤步骤进行交换。发现所构建的金属-DNA复合物是热稳定的。通过解析炔丙基修饰的DNA双链体的晶体结构并通过分子建模和模拟安装联吡啶配体来探索其结构。
• New Scaffolds for Supramolecular Chemistry: Upper-Rim Fully Tethered 5-Methyleneureido-5′-methyl-2,2′-bipyridyl Cyclodextrins
  作者：Romain Heck、Florence Dumarcay、Alain Marsura

  DOI：10.1002/1521-3765(20020603)8:11<2438::aid-chem2438>3.0.co;2-a

  日期：2002.6.3

  Seven upper-rim fully tethered cyclodextrins (URFT-CDs) have been synthesised in a good average coupling yield using the one-step "phosphine imide" approach and their metal complexation behaviour with lanthanides and transition metals was explored. We observed that the A-TE-E light conversion process (antennae effect) occurs in the URFT-CD lanthanide complexes. A molecular re ox switch based on the corresponding iron complexes is also reported. A reversible intramolecular translocation of the Fe-II and Fe-III ions, between two distinct binding cavities has been monitored spectroscopically and achieved by chemical triggering, Finally, a negative allosteric control of ion recognition through the formation of a CD pseudocryptand is discussed.
• Heptakis-6-(5-methylene-thioureido-5′-methyl-2,2′-bipyridyl)-β-cyclodextrin: synthesis and metal complexation study
  作者：Romain Heck、Alain Marsura

  DOI：10.1016/s0040-4039(03)00071-6

  日期：2003.2

  A new heptapode heptakis-6-(5-methylene-thioureido-5'-methyl-2,2'-bipyridyl)-beta-cyclodextrin was prepared and its complexation properties towards metal cations were investigated. Substituting the urea functions by the corresponding thioureas promoted the inversion of the metal coordination selectivity. Preliminary results showed the heptapode unable to complex lanthanides but authorise selective complexation of 'soft' and 'borderline' metal cations. (C) 2003 Elsevier Science Ltd. All rights reserved.