新型罗丹明类荧光探针中间体的合成及表征

Synthesis and structural characterization of the novel rhodamine probe intermediates

目的研究一类新型罗丹明类细胞钙离子荧光探针并合成一系列荧光中间体。方法以间氨基苯酚为起始原料,制备对甲苯磺酸(3-氨基)苯酚酯2,对甲苯磺酸(3-N,N-二烯丙基)苯酚酯3,对甲苯磺酸(3-N,N-二苄基)苯酚酯3’,在脱去对甲苯磺酸保护基后与邻苯二甲酸酐反应。结果合成荧光中间体N,N,N,N-四烯丙基取代罗丹明5和N,N,N,N-四苄基取代罗丹明6。得到对甲苯磺酸(3-N,N-二苄基)苯酚酯3’单晶结构。荧光中间体5和6的结构经核磁共振光谱,红外光谱,质谱证实。结论合成的新型荧光中间体,为性能优良的罗丹明类荧光探针的合成提供了新思路。

Aim To design a novel Rhodamine Ca2＋ fluorescence probe and synthesize some intermediates. Meth- ods 3-aminophenyl 4-methylbenzenesulfonate, 3-（ diallylamino ）phenyl 4-methylbenzenesulfonate and 3- （dibenzylamino） phenyl 4-methylbenzenesulfonate were prepared by using 3-aminophenol as raw materials and be- ing reacted with phthalic anhydride to give two novel unreported fluorescence Rhodamine derivatives. Results The structure of 3-（dibenzylamino） phenyl 4-methylbenzenesulfonate was characterized by X-ray single diffraction; meanwhile, the structure of other new compounds was confirmed by 1H NMR, IR spectra, MS and elemental analy- sis. Conclusion A new idea to synthese novel calcium fluorescence probes was provided by the novel fluorescence intermediates.