Homotriptycene analog compound and its preparing process
A compound, the technology of high three, applied in the field of high triptycene compounds, can solve the problem that the synthesis method has not been reported, achieve the effect of potential pharmacological activity and optoelectronic performance, solve the cost problem, and novel structure
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Embodiment 1
[0031] Add 100 mg of 10-(3,4,5-trimethoxybenzyl)anthrone (2a) (0.27 mmol) into a 25 ml three-neck flask, add 1 ml of diethylene glycol dimethyl ether, blow nitrogen, and stir at room temperature for 12 Minutes, add 40 mg of sodium borohydride, the solution turns red, stir at room temperature for 30 minutes, slowly add 0.5 ml of methanol dropwise, stir for 10 minutes, add 20 mg of sodium borohydride, spot the plate in 4 hours, the reaction is complete, add water, and quickly Stir, white crystals precipitate out, and put in the refrigerator. After filtration, 90 mg of white crystal 10-(3,4,5-trimethoxybenzyl)anthracenol (3a) was obtained. After testing, the yield is 90%, the melting point is 136-137°C, and the NMR test results are as follows:
[0032] 1 H NMR (400MHz, CDC1 3 )δ1.95(d, 3 J=10.4Hz, 1H), 2.91(d, 3 J=6.0Hz, 2H), 3.48(s, 6H), 3.76(s, 3H), 4.28(t, 3 J=6.0Hz, 1H), 4.76(d,3 J=10.8Hz, 1H), 5.61(s, 2H), 7.20(m, 2H), 7.26-7.66(m, 4H), 7.67(m, 2H); 13 C NMR (100MHz, ...
Embodiment 2
[0034] Add 232mg 10-(3,5-dimethoxybenzyl)-10-(3'-methoxybenzyl)anthrone (2d) (0.5mmol) in a 25mL three-necked flask, and add 2 mL of diethylene glycol dimethyl ether, stirred at room temperature for 12 minutes, added 60 mg of sodium borohydride, the solution turned red, stirred at room temperature for 30 minutes, slowly added 2 mL of methanol dropwise, stirred for 10 minutes, added 30 mg of sodium borohydride, and spotted the plate after 3 hours, and the reaction was complete , add water, stir rapidly under the ice-water bath, white crystals are precipitated, and put into the refrigerator. Filter to obtain 10-(3,5-dimethoxybenzyl)-10-(3-methoxybenzyl)anthracenol ( 3d) (228mg), the yield was 97.7% after detection; recrystallized with dichloromethane, ethanol and petroleum ether to obtain white crystal 3d (cis:trans=1:1), m.p.92~93℃; NMR detection The result is as follows:
[0035] 1 H NMR (400MHz, CDCl 3 )δ: 0.05(d, 3 J=11.6Hz, 1H, OH), 0.26(d, 3 J=11.6Hz, 1H, OH), 3.32(s,...
Embodiment 3
[0037] Add 100 mg of 10,10-bis(3,5-dibenzyloxy)benzyl anthrone (2f) (0.13 mmol) into a 25 ml three-neck flask, add 1 ml of diethylene glycol dimethyl ether, blow nitrogen, and keep at room temperature Stir for 12 minutes, add 25 mg of sodium borohydride, stir for 30 minutes, slowly add 0.5 ml of methanol dropwise, stir for 10 minutes, add 12 mg of sodium borohydride, spot the plate for 4 hours, and the reaction is complete. Add water and stir quickly, suck out the white solid and put it in the refrigerator. Filter and recrystallize with dichloromethane, ethanol and petroleum ether to obtain 94 mg of 10,10-bis(3,5-dibenzyloxy)benzyl anthracenol (3f) as colorless crystals. After testing, the yield was 94%, and the melting point was 43-45°C. The NMR detection results were as follows:
[0038] 1 H NMR (400MHz, CDCl 3 )δ0.32(d, 3 J=11.6Hz, 1H), 3.40(s, 2H), 3.61(s, 2H), 4.50(s, 4H), 4.52(s, 4H), 5.01(d, 3 J=11.6Hz, 1H), 5.50(d, 4 J=2.2Hz, 2H), 5.71(d, 4 J=2.2Hz, 2H), 6.14(t,...
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