6-methyl-2-phthalimidomethyl-3-benzyloxypyran-4-one | 812653-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 6-methyl-2-phthalimidomethyl-3-benzyloxypyran-4-one
• 英文别名: 2-phthalimidomethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one
• CAS: 812653-98-8
• 化学式: C₂₂H₁₇NO₅
• 分子量: 375.381
• InChiKey: YMYQNNZZQBPFRN-UHFFFAOYSA-N

物化性质

• 熔点：
  223-225 °C
• 沸点：
  603.0±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.82
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-methyl-2-phthalimidomethyl-3-benzyloxypyran-4-one 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以28%的产率得到(2-(aminomethyl)-3-(benzyloxy)-6-methyl-4H-pyran-4-one)
  参考文献：
  名称：

  调整三（羟基吡啶酮）配体的特性：用于 PET 成像的高效 68Ga 螯合剂†

  摘要：

  用于镓 68 的原型 tris(1,6-dimethyl-3-hydroxypyridin-4-one) 螯合剂 THP Me已显示出对 PET 放射性药物快速有效的基于试剂盒的68 Ga 标记的巨大希望。THP Me的肽衍生物已用于在临床前和临床研究中对其靶受体的体内表达进行成像。在此，我们描述了THP平台的新合成路线，包括用O （ tris (6-methyl- 3 -hydroxypyran-4-一, THPO) 和 N 1 –H (tris(6-methyl-3-hydroxypyridin-4-one), THP H) 组。研究了这些结构修饰对亲脂性、镓结合和金属离子选择性的影响。THP H能够在极其温和的条件下（5 分钟，室温，pH 6，1 μM 配体浓度）结合68 Ga，尤其是在体内，当对先前注射了68 Ga 醋酸盐的小鼠给药时。67 Ga 放射性标记的复合物在血清中稳定超过

  DOI：

  10.1039/c8dt04454f
• 作为产物：
  描述：

  2-hydroxymethyl-3-hydroxy-6-methyl-pyran-4(1H)-one 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 6-methyl-2-phthalimidomethyl-3-benzyloxypyran-4-one
  参考文献：
  名称：

  Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors

  摘要：

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.

  DOI：

  10.1021/jm049751s