4-(N-benzylmethylaminomethyl)-4'-methyl-2,2'-bipyridine | 330649-42-8

• 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: 4-(N-benzylmethylaminomethyl)-4'-methyl-2,2'-bipyridine
• 英文别名: bpyN；N-methyl-N-[[2-(4-methylpyridin-2-yl)pyridin-4-yl]methyl]-1-phenylmethanamine
• CAS: 330649-42-8
• 化学式: C₂₀H₂₁N₃
• 分子量: 303.407
• InChiKey: PQAGKJRJIKUEJF-UHFFFAOYSA-N

物化性质

• 沸点：
  433.4±40.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 4-(N-benzylmethylaminomethyl)-4'-methyl-2,2'-bipyridine 以 二氯甲烷 、 甲苯 为溶剂， 以96%的产率得到(4-(N-benzylmethylaminomethyl)-4'-methyl-2,2'-bipyridine)Re(CO)3Cl
  参考文献：
  名称：

  Rhenium Bipyridine Complexes for the Recognition of Glucose

  摘要：

  Bipyridine ligands containing pendant methyl, amino, and amino-boronic acid groups were synthesized. Coordination complexes of these ligands with rhenium were prepared straightforwardly and in good yield. The fluorescence behavior of the Re complexes was studied as a function of pH and exposure to various concentrations of glucose. The methyl bipyridine complex showed no change in fluorescence with pH, the amino derivative showed a rapid decrease from low pH to neutral, and the amino-boronate derivative showed little change from pH 4 to 10. Fluorescence quenching was observed at high pH as expected on the basis of a photoinduced electron transfer (PET) signaling mechanism. This behavior can be explained on the basis of the first oxidation and reduction potentials of these complexes. Glucose testing showed a significant dependence on the solvent system used. In pure methanol, the rhenium boronate complex exhibited a 55% fluorescence intensity increase upon increasing glucose concentration from 0 to 400 mg/dL. However, in 50 vol % methanollphosphate buffered saline, none of the complexes showed significant response in the glucose range of physiological interest.

  DOI：

  10.1021/ic010202b

文献信息

• Saccharide sensing molecules having enhanced fluorescent properties
  申请人：——

  公开号：US20020010279A1

  公开（公告）日：2002-01-24

  The present invention provides formulae for fluorescent compounds that have a number of properties which make them uniquely suited for use in sensors of analytes such as saccharides. The advantageous fluorescent properties include favorable excitation wavelengths, emission wavelengths, fluorescence lifetimes, and photostability. Additional advantageous properties include enhanced aqueous solubility, as well as temperature and pH sensitivity. The compound comprises an aryl or a substituted phenyl botonic acid that acts as a substrate recognition component, a fluorescence switch component, and a fluorophore. Fluorescent compounds are described that are excited at wavelengths greater than 400 nm and emit at wavelengths greater than 450 nm, which is advantageous for optical transmission through skin. The fluorophore is typically selected from transition metal-ligand complexes and thiazine, oxazine, oxazone, or oxazine-one as well as anthracene compounds. The fluorescent compound can be immobilized in a glucose permeable biocompatible polymer matrix that is implantable below the skin.

  本发明提供了一种荧光化合物的配方，具有多种特性，使它们非常适合用于传感器中，用于分析物如糖类。有利的荧光特性包括有利的激发波长、发射波长、荧光寿命和光稳定性。其他有利的特性包括增强的水溶性，以及温度和pH敏感性。该化合物包括作为底物识别组分、荧光开关组分和荧光物质的芳基或取代苯基硼酸。描述了被激发波长大于400纳米并且发射波长大于450纳米的荧光化合物，这对于通过皮肤进行光传输是有利的。荧光物质通常选自过渡金属配体络合物和噻嗪、噁嗪、噁醛或噻嗪-1以及蒽化合物。该荧光化合物可以固定在葡萄糖渗透生物相容性聚合物基质中，该基质可植入皮肤下方。
• US6682938B1
  申请人：——

  公开号：US6682938B1

  公开（公告）日：2004-01-27
• US6673625B2
  申请人：——

  公开号：US6673625B2

  公开（公告）日：2004-01-06
• Rhenium Bipyridine Complexes for the Recognition of Glucose
  作者：Douglas R. Cary、Natasha P. Zaitseva、Kelsey Gray、Kira E. O'Day、Christopher B. Darrow、Stephen M. Lane、Thomas A. Peyser、Joe H. Satcher,、William P. Van Antwerp、A. J. Nelson、John G. Reynolds

  DOI：10.1021/ic010202b

  日期：2002.3.1

  Bipyridine ligands containing pendant methyl, amino, and amino-boronic acid groups were synthesized. Coordination complexes of these ligands with rhenium were prepared straightforwardly and in good yield. The fluorescence behavior of the Re complexes was studied as a function of pH and exposure to various concentrations of glucose. The methyl bipyridine complex showed no change in fluorescence with pH, the amino derivative showed a rapid decrease from low pH to neutral, and the amino-boronate derivative showed little change from pH 4 to 10. Fluorescence quenching was observed at high pH as expected on the basis of a photoinduced electron transfer (PET) signaling mechanism. This behavior can be explained on the basis of the first oxidation and reduction potentials of these complexes. Glucose testing showed a significant dependence on the solvent system used. In pure methanol, the rhenium boronate complex exhibited a 55% fluorescence intensity increase upon increasing glucose concentration from 0 to 400 mg/dL. However, in 50 vol % methanollphosphate buffered saline, none of the complexes showed significant response in the glucose range of physiological interest.