4-(N-[o-(5,5-dimethylborinan-2-yl)benzyl]-N-[methylamino]methyl)-4'-methylbipyridine | 330649-43-9

• 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: 4-(N-[o-(5,5-dimethylborinan-2-yl)benzyl]-N-[methylamino]methyl)-4'-methylbipyridine
• 英文别名: N-[[2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]methyl]-N-methyl-1-[2-(4-methylpyridin-2-yl)pyridin-4-yl]methanamine
• CAS: 330649-43-9
• 化学式: C₂₅H₃₀BN₃O₂
• 分子量: 415.343
• InChiKey: FJVSSMOSNRPFOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 4-(N-[o-(5,5-dimethylborinan-2-yl)benzyl]-N-[methylamino]methyl)-4'-methylbipyridine 以 二氯甲烷 、 甲苯 为溶剂， 以99%的产率得到(4-(N-[o-(5,5-dimethylborinan-2-yl)benzyl]-N-[methylamino]methyl)-4'-methylbipyridine)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
• 作为产物：
  描述：

  5,5-dimethyl-2-(2-[(methylamino)methyl]phenyl)-1,3,2-dioxaborinane 、 4-(溴甲基)-4-甲基-2,2-联吡啶 以 四氢呋喃 为溶剂， 以51%的产率得到4-(N-[o-(5,5-dimethylborinan-2-yl)benzyl]-N-[methylamino]methyl)-4'-methylbipyridine
  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

• 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.