A kind of indole vinyl compound and its preparation method and application
An indole ethylene and compound technology, applied in the field of fluorescent probes, can solve the problems of affecting application value, high phototoxicity, poor photostability, etc., and achieve the effects of intuitive biological detection reagents, low biological toxicity, and strong photostability
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[0054] The present invention also provides a preparation method of indole vinyl compounds, comprising:
[0055] Formula (II) compound, formula (III) compound, R 2 -H reaction, obtains the indole vinyl compound of formula (I) structure;
[0056]
[0057] Among them, R 1 , R 3 independently selected from H, halogen, hydroxyl, C1-C6 alkoxy, C2-C15 imino, C1-C6 alkyl;
[0058] R 4 Alkyl group selected from C1~C6;
[0059] R 2 selected from piperidinyl, morpholinyl, pyrrolyl or NR 5 R 6 ;
[0060] R 5 , R 6 independently selected from H, -CH 3 、-CH 2 CH 3 、-CH 2 CH 2 OH, -CH 2 CH 2 CH 2 OH, formula (R-1), formula (R-2), formula (R-3), formula (R-4) or formula (R-5),
[0061] and R 5 , R 6 Not H at the same time.
[0062] According to the present invention, the present invention will formula (II) compound, formula (III) compound, R 2 -H reaction to obtain indole vinyl compounds; wherein, the limitation of each group is the same as the limitation of the ...
Embodiment 1
[0074] Embodiment 1: the synthesis of compound 2 (4-chloro-1,2-dimethylquinoline)
[0075] Weigh 0.2g (1.1236mmol) of 4-chloro-2-methylquinoline into a 25ml round bottom flask, add methyl iodide and solvent sulfolane, heat the mixture to 40-60°C, react for 15 hours, cool, add Shake it with anhydrous ether, filter it with suction, wash the solid several times, and weigh it after vacuum drying. Thin-layer chromatography shows that there is no by-product, and 0.345 g of pure product 2 is obtained with a yield of 95.8%.
[0076] 1 H NMR (400MHz, DMSO) δ8.56(d, J=8.4Hz, 1H), 8.46(d, J=8.3Hz, 1H), 8.22(t, J=8.1Hz, 1H), 8.01(t, J =7.9Hz, 1H), 7.55(s, J=7.4Hz, 1H), 4.20(s, 3H), 3.74(s, 1H), 2.68(s, 3H).
Embodiment 2
[0077] Embodiment 2: the synthesis of compound (I-a)
[0078] Weigh 0.319g (0.001mol) of compound 2, add it to a round bottom flask with 10ml of ethanol, then add 0.217g, which is 1.5 times the molar amount of indole-3-carboxaldehyde, stir at room temperature for 5 minutes, then add 1ml of piperidine, reacted at 80°C for 5h, cooled to room temperature, added 10ml of ethyl acetate to the reacted solution, oscillated, filtered with suction, washed the precipitate with a small amount of ethanol, and dried in vacuo to obtain compound (I-a) as a tan solid 0.409 g, its structure is as follows, the yield is 85.1%: 1H NMR (400MHz, DMSO) δ11.82 (s, 1H), 8.27 (d, J=8.8Hz, 1H), 8.11 (d, J=8.3Hz, 1H ), 8.05-7.98(m, 2H), 7.74(t, J=7.6Hz, 1H), 7.63(dd, J=11.8, 9.1Hz, 2H), 7.51-7.43(m, 2H), 7.25(t, J=7.6Hz, 1H), 7.06(t, J=7.5Hz, 1H), 6.98(s, 1H), 4.23(s, 3H), 3.76(s, 4H), 1.84(s, 4H), 1.78( s, 2H).
[0079]
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