ACCEPTED MANUSCRIPT
Petroleum ether : Ethyl acetate 20 : 1, to afford product 1 as a white solid (7.0 g, 67%).
1H NMR (CDCl3, 400 MHz, 298 K ), δ (ppm): 9.87 (s, 1H), 7.85 (d, J = 8.4 Hz ,2H),
6.98 (d, J = 8.4 Hz ,2H), 4.03 (t, J = 6.5 Hz, 2H), 3.40 (t, J = 6.9 Hz, 2H), 1.89-1.76
(m, 4H), 1.51-1.38 (m, 4H), 1.35 -1.23 (m, 12H). 13C NMR (CDCl3, 100 MHz), δ
(ppm): 190.8, 164.2, 132.0, 129.7, 114.8, 68.4, 34.0, 32.8, 29.5, 29.4, 29.3, 29.1, 28.8,
28.2, 25.9.
2.4 Synthesis of 4-(12-butylamino-butoxy)-benzaldehyde 2:
1 (2.0 g, 7.8 mmol) was dissolved in 50 ml dichloromethane, the solution was then
o
cooled under 0 C. The n-butylamine (2.8 g, 38.7 mmol) was added in the form of a
drop. When drop finished, being risen temperature to room temperature and stirred for
12 hours. The solvent was removed by using rotary evaporation under vacuum, and
the gained white solid was dissolved in 100 ml dichloromethane and washed brine
3×100 ml, the combined organic layer was dried over Na2SO4, filtered and evaporated
solvent under vacuum, the residue was further purified by flash column
chromatography, eluting with Petroleum ether : Ethyl acetate 20 : 1. To yield 2 as a
1
white solid (1.5 g, 77%). H NMR (CDCl3, 400 MHz, 298 K), δ (ppm): 9.85 (s, 1H),
9.20-9.51 (s, 1H), 7.80 (d, J = 8.4 Hz, 2H), 6.96 (d, J = 8.4 Hz, 2H), 4.01 (t, J = 6.4
Hz, 2H), 2.88 (t, J = 6.2 Hz, 4H), 1.85 (m, 4H), 1.77 (m, 2H), 1.40 (m, 4H), 1.37-1.18
(m, 14H), 0.93 (t, J = 7.3 Hz, 3H). 13C NMR (CDCl3, 100 MHz), δ (ppm): 190.9,
164.3, 132.0, 129.7, 114.7, 68.4, 47.8, 47.5, 29.5, 29.5, 29.4, 29.3, 29.1, 27.8, 26.9,
25.9, 25.9, 20.1, 13.5. HRMS (ESI) (m/z): [M+H]+ calcd for C23H40NO2 , 362.3054;
+
found, 362.3022.
2.5 Synthesis of Aurones derivative 3:
2,3- dihydrobenzo [b] furan-3-one (1.1g, 8.0 mmol) and 2 (2.0 g, 8.0 mmol) and
were dissolved in 30 ml dichloromethane, Al2O3 was then added at room temperature,
the suspension was stirred in the darkness for 10 hours. After complete consumption
of the starting material (monitored by TLCs, dichloromethane : methanol 20:1), the
reaction mixture was filtered to remove Al2O3. The filter cake was washed with
dichloromethane to colorless. The filtrate was wash using brine, dried over Na2SO4,
filter and remove solvent by rotary evaporation under vacuo and the residue was
further purified by flash column chromatography, elucting with dichloromethane :
methanol 20:1. To afford 3 as a white solid (1.2 g, 40%). 1H NMR (CDCl3. 400 MHz,
298 K), δ (ppm) 7.82 (d, J = 8.1 Hz, 2H), 7.81 (d, J = 8.3 Hz 2H), 7.65 (t, J = 6.6Hz,
1H), 7.33 (d, J = 8.1Hz, 1H), 7.22 (t, J = 8.0 Hz, 1H), 6.98 (d, J = 8.3Hz, 2H), 6.90 (s,
1H), 4.03 (t, J = 6.5Hz, 2H), 2.90 (t, J = 6.3 Hz, 4H), 1.70-1.20 (m, 4H), 1.82-1.76 (m,
2H), 1.40-1.30 (m, 4H), 1.30-1.20(m, 14H), 0.95 (t, J = 7.5Hz, 3H) 13C NMR (CDCl3,