5,5-dimethyl-2-(2-[(methylamino)methyl]phenyl)-1,3,2-dioxaborinane | 95752-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5-dimethyl-2-(2-[(methylamino)methyl]phenyl)-1,3,2-dioxaborinane
• 英文别名: 2,2-dimethylpropane-1,3-diyl[o-(methylaminomethyl)phenyl]boronate；1-[2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]-N-methylmethanamine
• CAS: 95752-88-8
• 化学式: C₁₃H₂₀BNO₂
• 分子量: 233.118
• InChiKey: VVMCXGNHCDIRBF-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C
• 沸点：
  351.7±25.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  30.49
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 、 2-((甲基氨基)甲基)苯基硼酸 以84%的产率得到
  参考文献：
  名称：

  LAUER, M.;BOEHNKE, H.;GROTSTOLLEN, R.;SALEHNIA, MOHAMMAD;WULFF, G., CHEM. BER., 1985, 118, N 1, 246-260

  摘要：

  DOI：

文献信息

• Arylboronic acids with intramolecular B–N interaction: convenient synthesis through ortho-lithiation of substituted benzylamines
  作者：Manfred Lauer、Günter Wulff

  DOI：10.1016/s0022-328x(00)99290-8

  日期：1983.11
• LAUER, M.;WULFF, G., J. ORGANOMET. CHEM., 1983, 256, N 1, 1-9
  作者：LAUER, M.、WULFF, G.

  DOI：——

  日期：——