4-methylpyridine-1-15N | 362030-62-4

• 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-methylpyridine-1-15N
• CAS: 362030-62-4
• 化学式: C₆H₇N
• 分子量: 94.1216
• InChiKey: FKNQCJSGGFJEIZ-CDYZYAPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  7.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 4-methylpyridine-1-15N 以37%的产率得到2-(pyridin-4-yl-15N)ethan-1-ol
  参考文献：
  名称：

  Photoinduced Proton Transfer in a Pyridine Based Polymer Gel

  摘要：

  We describe an experimental and theoretical consideration of photoexcited proton transfer in a poly(4-vinyl pyridine)/pyridine gel. Evidence was found for two states of a multiple state process analyzed by DFT modeling. According to the latter, following irradiation at 385 nm, the proton donor is the CH group of the polymer main chain and the proton acceptor is the nitrogen of the polymeric pyridine side chain. Proton transfer is made possible through the assistance of a mobile pyridine solvent molecule acting as a transfer vehicle. Proton transfer promotes both a geometrical rearrangement of the vinyl side chain as well as electronic density redistribution. The photoproduct intermediate the hydrogen-bonded complex between the protonated solvent pyridine molecule and the deprotonated polymeric pyridine side chain is identified by its Curie law magnetic susceptibility, ESR spectrum, and fluorescence lifetime measurements. The proton transfer from the nitrogen of the solvent pyridine molecule to the pyridine side chain nitrogen, producing pyridinium, is a thermodynamically favorable relaxation process and occurs without an energy barrier. The protonation of nitrogen on the polymeric side chain was detected by solid state NMR spectroscopy performed on a polymer enriched enriched gel. The calculations and experimental data suggest a central role for the gel solvent molecule as a catalytic agent and proton transfer vehicle. The process suggested by DFT modeling may have relevance for photosensitive devices in part due to the fact that we have been able to show that long-lived paramagnetism may be included among the inducible properties of soft polymer gels.

  DOI：

  10.1021/jp104277r
• 作为产物：
  描述：

  4-甲基吡啶 在 ¹⁵N-ammonium chloride 、 sodium acetate 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 12.5h， 生成 4-methylpyridine-1-15N
  参考文献：
  名称：

  通过锌亚胺中间体合成 15N-吡啶和高质量同位素

  摘要：

  掺入稳定放射性同位素的方法是制药和农用化学品开发不可或缺的一部分。然而，尽管吡啶在候选化合物中普遍存在，但在其结构中掺入 15个 N 原子的方法是有限的。在这里，我们提出了一种吡啶 15N 标记的通用方法，该方法通过开环到 NTf-Zincke 亚胺，然后用市售的 15NH4Cl 盐闭合。该工艺适用于一系列取代的吡啶，从简单的构建块型化合物到复杂药物的后期标记，在大多数情况下，15N 掺入率为 >95%。锌亚胺中间体的反应性还能够使吡啶 C3 和 C5 位点的氘化，从而在药物开发过程中对生物液体进行 LCMS 分析所需的高质量同位素。

  DOI：

  10.1021/jacs.3c12445