Fluorine-substituted diphenylethane compound and preparation method and application thereof
A technology of diphenylethane and compounds, applied in the field of drug synthesis, can solve the problems of harsh reaction conditions, tumor cell apoptosis, and many by-products, and achieve simple and easy preparation conditions, strong in vitro anti-tumor activity, and few by-products Effect
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Embodiment 1
[0042] Synthesis of (E)-2-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylic acid (3a), see figure 1 :
[0043]Dissolve 3,4,5-trimethoxybenzaldehyde (7.9g, 40mmol) and p-methoxyphenylacetic acid (6.7g, 40mmol) in 150mL of acetic anhydride, then add triethylamine (8.1g, 80mmol) , The mixture was heated at 110° C. for 6 h. After cooling, it was acidified with concentrated hydrochloric acid, poured into ice water, and stirred for 4 hours to obtain a light yellow solid, which was filtered, dissolved in 10% NaOH aqueous solution, washed with ethyl acetate to decolorize, separated the organic layer, and kept the aqueous phase. Hydrochloric acid was added to the aqueous phase until pH = 3-4. The precipitated solid was filtered and recrystallized from ethyl acetate to obtain 3a, 11.0 g, yield 80.2%, white solid, mp: 188.6-189.3°C.
[0044] 1 H NMR (500MHz, CDCl 3 ): δ7.82(s,1H),7.20(d,J=10.0Hz,2H),6.96(d,J=5.0Hz,2H),6.37(s,2H),3.81(s,6H),3.58 (s,6H);
[0045] 13 C NMR (125MHz...
Embodiment 2
[0078] Preparation of 1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-ol (7a), see figure 1 :
[0079] 5a (1.6 g, 5 mmol) was dissolved in 30 mL of absolute ethanol, and NaBH was added in portions at 0 °C 4 (0.3g, 7.5mmol), stirred for half an hour, returned to room temperature and reacted overnight. Quenched with water, extracted with ethyl acetate, combined organic phases, dried over anhydrous sodium sulfate, filtered, and spin-dried, the residue was purified by silica gel chromatography to obtain 7a (1.0 g, yield 65.0%), which was directly used in the next reaction.
[0080] Preparation of 5-(2-fluoro-2-(4-methoxyphenyl)ethyl)-1,2,3-trimethoxybenzene (8a):
[0081] It is one of the fluorine-substituted diphenylethane compounds in the present invention.
[0082] Dissolve 7a in dichloromethane, add DAST (0.8g, 4.7mmol) dropwise at 0°C and stir for half an hour, return to room temperature, stir for 18h, TLC monitors that the reaction is complete, drop ice water to que...
Embodiment 3
[0084] For the preparation of 1-(3-(benzyloxy)-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-ol (7b), see figure 1 :
[0085] 5b (1.6g, 5mmol) was dissolved in 30mL of absolute ethanol, NaBH4 (0.3g, 7.5mmol) was added in batches at 0°C, stirred for half an hour, returned to room temperature and reacted overnight. Quenched with water, extracted with ethyl acetate, combined organic phases, dried over anhydrous sodium sulfate, filtered, and spin-dried, the residue was purified by silica gel chromatography to obtain 7b (1.3 g, yield 64.5%), which was directly used in the next reaction.
[0086] Preparation of 5-(1-fluoro-1-(3-(benzyloxy)-4-methoxyphenyl)ethyl)-1,2,3-trimethoxybenzene (8c), which is the subject of the present invention One of the fluorine-substituted diphenylethane compounds. see figure 1 .
[0087] Dissolve 7b in dichloromethane, add DAST (0.8g, 4.7mmol) dropwise at 0°C and stir for half an hour, return to room temperature, stir for 18h, TLC monitors that...
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