5-aminomethyl-5'-methyl-2,2'-bipyridine | 227619-68-3

• 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-aminomethyl-5'-methyl-2,2'-bipyridine
• 英文别名: (5'-Methyl-[2,2'-bipyridin]-5-yl)methanamine；[6-(5-methylpyridin-2-yl)pyridin-3-yl]methanamine
• CAS: 227619-68-3
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: HHSZDEQELWSMMH-UHFFFAOYSA-N

物化性质

• 沸点：
  368.6±42.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 hexakis-(2,3-di-O-methyl-6-deoxy-6-azido)-cyclomaltohexaose 、 5-aminomethyl-5'-methyl-2,2'-bipyridine 在 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以35%的产率得到hexakis-[2,3-di-O-methyl-6-deoxy-6-(5-methyleneureido-5'-methyl-2,2'-bipyridyl)]-cyclomaltohexaose
  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
• 作为产物：
  描述：

  5 5'-二甲基-2,2'-二吡啶 在 10percent Pd/C N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 偶氮二异丁腈 、 氢气 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.8h， 生成 5-aminomethyl-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

• Upper-rim alternately tethered α-cyclodextrin molecular receptors: synthesis, metal complexation and interfacial behavior
  作者：Stephane Menuel、Yohann Corvis、Ewa Rogalska、Alain Marsura

  DOI：10.1039/b809151j

  日期：——

  Three novel α-cyclodextrin tripods bearing three ureido-bipyridyl tethers symmetrically distributed on their upper rim in the A,C,E positions and alternated with hydroxyl, acetyl or lauryl moieties were prepared by the tandem Staudinger–Aza–Wittig alias“phosphine imide” strategy. The functionalisations on the cyclodextrin upper rim allowed a fine-tuning of the metal complexation and amphiphilic properties.

  通过串联的Staudinger–Aza–Wittig（又称“磷氮酰胺”）策略，制备了三种新型α-环糊精三脚架，三种尿素-双吡啶连接体对称地分布在其上缘的A、C、E位置，并与羟基、乙酰基或月桂基交替排列。环糊精上缘的功能化使得金属络合和两亲性特性的微调成为可能。
• Stepwise and Dramatic Enhancement of Anion Recognition with a Triple-Site Receptor Based on the Calix[4]arene Framework Using Two Different Cationic Effectors
  作者：Tatsuya Nabeshima、Toshiyuki Saiki、Jun Iwabuchi、Shigehisa Akine

  DOI：10.1021/ja042882y

  日期：2005.4.1

  Synthesis and binding behavior of a novel multi-responsive host 1, in which two esters, two polyether moieties, two urea sites, and two bipyridine units as ion binding sites are arranged on the calix[4]arene skeleton, is reported. 1 recognizes Na+ and Ag+ simultaneously and quantitatively and captures an anionic guest. The ability of 1 to recognize anions, including CF3SO3- and BF4-, remarkably increases in a stepwise manner using Na+ and Ag+ as effectors. The enhancement of the K. eventually reaches factors of 1500 and 2000 for NO3- and CF3SO3-, respectively, in the presence of both Na+ and Ag+, compared to the free 1. The regulation of binding of multiple ligands may be applicable to multistep cascade systems for the amplification of molecular events, and further studies in this field could provide insight applicable to more advanced molecular devices.
• Multi-step regulation of anion recognition by redox-active pseudocryptand
  作者：Tatsuya Nabeshima、Sayuri Masubuchi、Norie Taguchi、Shigehisa Akine、Toshiyuki Saiki、Soichi Sato

  DOI：10.1016/j.tetlet.2006.12.143

  日期：2007.2

  We synthesized an artificial redox-active Fe-pseudocryptand as an anion receptor to respond to electrochemical oxidation and reduction. Spectroscopic study and X-ray crystallography showed that the assembled urea chains and the isocyanuric platform generate an anion-binding cavity through favorable multiple hydrogen bonds and anion-pi interactions. As the positive charge of the Fe center increases, the anion affinity is effectively increased due to an enhanced electrostatic interaction between the Fe atom and the anionic guest. This is the first efficient multi-step regulation of Cl- selective anion recognition by the redox-active pseudocryptand. (c) 2007 Elsevier Ltd. All rights reserved.
• A new symmetrically modified α-cyclodextrin tripode: selective metal complexation and fluorescence properties
  作者：Romain Heck、Alain Marsura

  DOI：10.1016/j.tetlet.2003.10.172

  日期：2004.1

  A new tripodal a-cyclodextrin having three ureido-bipyridyl tethers symmetrically distributed on its upper rim was prepared in one step by the polymer supported 'phosphine imide' reaction in a medium yield. As expected, the highly selective complexation properties towards 'hard' and 'soft' cations were maintained with regards to the URFT-Cd (upper rim fully tethered) family previously investigated. Its Eu-III and Tb-III lanthanide complex fluorescence behaviour clearly indicates that a limited number of tethers allow a better bis-heterocyclic antenna self-organisation around the cation leading to enhanced fluorescence properties. (C) 2003 Elsevier Ltd. All rights reserved.
• Heptakis-6-(5-methylene-ureido-5′-methyl-2,2′-bipyridinyl)-cyclomaltoheptaose as a new fluorescent lanthanide polydentate ligand
  作者：F. Charbonnier、Thierry Humbert、Alain Marsura

  DOI：10.1016/s0040-4039(99)00668-1

  日期：1999.5

  The present work describes the one-pot synthesis of an heptakis-(bipyridinyl-ureido)-beta-cyclodextrin in a high coupling average (82%) by the "phosphinimine" approach. The subsequent complexation of 3 with EuCl3 or TbCl3 gives stable complexes 4. Preliminary results on complexation and fluorescence properties are reported. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.