2-(4′-methoxystyryl)pyridine N-oxide | 10434-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4′-methoxystyryl)pyridine N-oxide
• 英文别名: 2-(4'-methoxystyryl)pyridine；2-[2-(4-Methoxy-phenyl)-vinyl]-pyridine 1-oxide；2-[2-(4-methoxyphenyl)ethenyl]-1-oxidopyridin-1-ium
• CAS: 10434-74-9
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: JAQHCTLLLPXFKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4′-methoxystyryl)pyridine N-oxide 、 trimethoxonium tetrafluoroborate 以 二氯甲烷 为溶剂， 以73%的产率得到N-methoxy-2-(4'-methoxystyryl)pyridinium tetrafluoroborate
  参考文献：
  名称：

  N-Alkoxyheterocycles As Irreversible Photooxidants

  摘要：

  AbstractIrreversible photooxidation based on N–O bond fragmentation is demonstrated for N‐methoxyheterocycles in both the singlet and triplet excited state manifolds. The energetic requirements for bond fragmentation are studied in detail. Bond fragmentation in the excited singlet manifold is possible for ππ* singlet states with energies significantly larger than the N–O bond dissociation energy of ca 55 kcal mol−1. For the nπ* triplet states, N–O bond fragmentation does not occur in the excited state for orbital overlap and energetic reasons. Irreversible photooxidation occurs in the singlet states by bond fragmentation followed by electron transfer. Irreversible photooxidation occurs in the triplet states via bimolecular electron transfer to the donor followed by bond fragmentation. Using these two sensitization schemes, donors can be irreversibly oxidized with oxidation potentials ranging from ca 1.6–2.2 V vs SCE. The corresponding N‐ethylheterocycles are characterized as conventional reversible photooxidants in their triplet states. The utility of these sensitizers is demonstrated by irreversibly generating the guanosine radical cation in buffered aqueous solution.

  DOI：

  10.1111/php.12227
• 作为产物：
  描述：

  2-甲基吡啶氧化物 、 potassium tert-butylate 、 4-甲氧基苯甲醛 在 title compound 作用下， 生成 2-(4′-methoxystyryl)pyridine N-oxide
  参考文献：
  名称：

  Conjugated aromatic compounds with a pyridine substituent

  摘要：

  本发明涉及式的化合物。本发明的化合物是NMDA（N-甲基-D-天冬氨酸）受体亚型阻滞剂，用于治疗与该受体相关的疾病。

  公开号：

  US20060058354A1