摘要
4-氟苯乙酮经二氧化硒氧化得到4-氟苯甲酰甲酸(1);1与盐酸氨基脲在碱性条件下经环合反应制得5-(4-氟苯基)-6-氮杂嘧啶(2);2与1-乙酰氧基-2,3,5-三苯甲酰氧基-1-β-D-呋喃核糖在无水乙腈中反应得2',3',5'-三苯甲酰氧基-5-(4-氟苯基)-6-氮杂尿苷(3);3在甲醇中水解合成了一种新型荧光核苷探针——5-(4-氟苯基)-6-氮杂尿苷(4),其结构经1H NMR,13C NMR和MS(ESI)表征。并研究了4的性能。结果表明:4在水中的量子产率高达0.81,对极性变化敏感;4可选择性识别Pd2+,在5.0×10-7~5.0×10-6mol·L-1能定量检测Pd2+。
4-Fluorobenzoylformic acid（1 ） was prepared by oxidation reaction of 4-fluoroacetophenone with selenium dioxide. Cyclization of 1 with semicarbazide hydrochloride under alkaline conditions gave 5-（4-fluorophenyl） -6-aza uracil （ 2 ）. 5-（ 4-fluorophenyl ） -6-aza-2＇, 3＇, 5＇-tribenzoyl-uridine （ 3 ） was obtained by the reaction of 2 with 1-O-acetyl-2,3,5-tri-O-benzoyl-fl-D-ribofuranose in anhydrous acetonitrile. A novel fluorescent nucleoside probe, 5-（4-fluorophenyl） -6-aza uridine （ 4）, was synthesized by hydrolysis of 3 in methanol. The structure was characterized by 1H NMR, 13C NMR and MS （ESI）. In addition, the properties of 4 were also investigated. The results showed that the quantum yield of 4 was up to 0.81 in water and it was very sensitive to environmental polarity. A study of the recognition effect of 4 for different metal cations was carried out. The result indicated that 4 exhibited good selec- tivity toward Pd2＋ in the range of 5.0 × 10 -7 -5.0 × 10 -6 mol·L-1
出处
《合成化学》
CAS
CSCD
2017年第10期803-808,共6页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(21562041)
中央高校基本科研业务费(JUSRP115A08)
