3-benzyloxy-2-methyl-1-naphthyl-4-pyridinone | 1256623-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-benzyloxy-2-methyl-1-naphthyl-4-pyridinone
• 英文别名: 2-Methyl-1-naphthalen-1-yl-3-phenylmethoxypyridin-4-one；2-methyl-1-naphthalen-1-yl-3-phenylmethoxypyridin-4-one
• CAS: 1256623-56-9
• 化学式: C₂₃H₁₉NO₂
• 分子量: 341.409
• InChiKey: ZRKBUZJUHRVQBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-2-methyl-1-naphthyl-4-pyridinone 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到3-hydroxy-2-methyl-1-naphthyl-4-pyridinone hydrochloride
  参考文献：
  名称：

  Microwave-assisted synthesis of 3-hydroxy-4-pyridinone/naphthalene conjugates. Structural characterization and selection of a fluorescent ion sensor

  摘要：

  Two novel 3-hydroxy-4-pyridinone/naphthalene conjugates (L1 and L2) with different distances between the chelating and the fluorescent moieties were synthesized using conventional heating and microwave irradiation achieving a shorter reaction time. The structure of both compounds was confirmed by X-ray crystallography, revealing that these compounds were isolated as hydrochloride salts in dihydroxypyridinium forms. In solution and in the presence of a base, the tautomeric keto forms may be obtained as it was elucidated by NMR analysis. The dihydroxypyridinium form of L1 exhibits fluorescence at 450 nm, both in ACN and DMSO, whereas the corresponding keto form exhibits fluorescence at 365 nm. In contrast, the dihydroxypyridinium form of L2 only fluoresces in DMSO, exhibiting a band at 340 nm, while the keto form is non-fluorescent. These distinct fluorescent behaviors reveal that the tautomeric form in which the ligands are isolated and the distance between the chelating and fluorescent functions strongly influences their fluorescence properties. Ligand L1 exhibits better fluorescence properties and its fluorescence intensity is quenched in the presence of variable concentration of Cu2+, Zn2+, and Fe3+, thus making it suitable to be used as ion sensor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.065
• 作为产物：
  描述：

  3-(苄氧基)-2-甲基-4H-吡喃-4-酮 、 1-萘胺 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以52%的产率得到3-benzyloxy-2-methyl-1-naphthyl-4-pyridinone
  参考文献：
  名称：

  Microwave-assisted synthesis of 3-hydroxy-4-pyridinone/naphthalene conjugates. Structural characterization and selection of a fluorescent ion sensor

  摘要：

  Two novel 3-hydroxy-4-pyridinone/naphthalene conjugates (L1 and L2) with different distances between the chelating and the fluorescent moieties were synthesized using conventional heating and microwave irradiation achieving a shorter reaction time. The structure of both compounds was confirmed by X-ray crystallography, revealing that these compounds were isolated as hydrochloride salts in dihydroxypyridinium forms. In solution and in the presence of a base, the tautomeric keto forms may be obtained as it was elucidated by NMR analysis. The dihydroxypyridinium form of L1 exhibits fluorescence at 450 nm, both in ACN and DMSO, whereas the corresponding keto form exhibits fluorescence at 365 nm. In contrast, the dihydroxypyridinium form of L2 only fluoresces in DMSO, exhibiting a band at 340 nm, while the keto form is non-fluorescent. These distinct fluorescent behaviors reveal that the tautomeric form in which the ligands are isolated and the distance between the chelating and fluorescent functions strongly influences their fluorescence properties. Ligand L1 exhibits better fluorescence properties and its fluorescence intensity is quenched in the presence of variable concentration of Cu2+, Zn2+, and Fe3+, thus making it suitable to be used as ion sensor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.065

文献信息

• Microwave-assisted synthesis of 3-hydroxy-4-pyridinone/naphthalene conjugates. Structural characterization and selection of a fluorescent ion sensor
  作者：Ana M.G. Silva、Andreia Leite、Mariana Andrade、Paula Gameiro、Paula Brandão、Vítor Felix、Baltazar de Castro、Maria Rangel

  DOI：10.1016/j.tet.2010.08.065

  日期：2010.10

  Two novel 3-hydroxy-4-pyridinone/naphthalene conjugates (L1 and L2) with different distances between the chelating and the fluorescent moieties were synthesized using conventional heating and microwave irradiation achieving a shorter reaction time. The structure of both compounds was confirmed by X-ray crystallography, revealing that these compounds were isolated as hydrochloride salts in dihydroxypyridinium forms. In solution and in the presence of a base, the tautomeric keto forms may be obtained as it was elucidated by NMR analysis. The dihydroxypyridinium form of L1 exhibits fluorescence at 450 nm, both in ACN and DMSO, whereas the corresponding keto form exhibits fluorescence at 365 nm. In contrast, the dihydroxypyridinium form of L2 only fluoresces in DMSO, exhibiting a band at 340 nm, while the keto form is non-fluorescent. These distinct fluorescent behaviors reveal that the tautomeric form in which the ligands are isolated and the distance between the chelating and fluorescent functions strongly influences their fluorescence properties. Ligand L1 exhibits better fluorescence properties and its fluorescence intensity is quenched in the presence of variable concentration of Cu2+, Zn2+, and Fe3+, thus making it suitable to be used as ion sensor. (C) 2010 Elsevier Ltd. All rights reserved.