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CAS No. : | 485-72-3 | MDL No. : | MFCD00016948 |
Formula : | C16H12O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HKQYGTCOTHHOMP-UHFFFAOYSA-N |
M.W : | 268.26 | Pubchem ID : | 5280378 |
Synonyms : |
Biochanin B;Flavosil;Formononetol Formononetin;NSC 93360;Formononetol
|
Chemical Name : | 7-Hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.8% | With pyridine; In dichloromethane; for 2h;Reflux; | A solution of p-methoxyphenylpropionic acid (12a, 2.99 mmol), SOCl2 (2 mL) and DMF (2 drops) was added to toluene (20 mL) and stirred at 75C for 3 h. The reaction was terminated and the solution was concentrated to dryness under reduced pressure to give p-methoxyphenylpropionyl chloride (13a)The 7-hydroxy-3- (4-methoxyphenyl) -4H-benzopyran-4-one(6,2.61 mmol), pyridine (1 mL) in CH2Cl2 (10 mL) was added dropwise with p-methoxyphenylpropionyl chloride (13a) with stirring. After completion of the dropwise addition, the reaction was refluxed for 2 h. The reaction was completed, cooled to room temperature, poured into dilute hydrochloric acid, stirred. Extracted with dichloromethane, and washed with saturated brine. The solvent was concentrated to dryness under reduced pressure to give crude product. Column chromatography (petroleum ether / ethyl acetate: 15/1, V / V) gave a white solid in 66.8% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With dmap; In ethanol; at 78℃; | General procedure: A solution of 2a-h (2 mmol) in EtOH (anhydrous,30 mL) was refluxed and treated with anabasine (2.5 mmol), paraformaldehyde (90 mg, 3 mmol), and DMAP (2-5 mg).The mixture was refluxed for 20-25 h. The end of the reaction was determined using TLC. The mixture was cooled and diluted with hexane. The resulting precipitate was filtered off, dried, and crystallized from i-PrOH-hexane or purified bycolumn chromatography using EtOAc as eluent.7-Hydroxy-3-(4-methoxyphenyl)-8-[(2S)-2-pyridin-3-ylpiperidin-1-yl]methyl}-4H-chromen-4-one (3a). Yield75%, C27H26N2O4, mp 102-104C. IR spectrum (KBr, nu, cm-1): 2940, 2595, 1629, 1512, 1444, 1294, 1267, 1247, 1179, 835.MS (CI): 443.1 ([M + H]+, 100%). 1H NMR spectrum (400 MHz, CDCl3, delta, ppm, J/Hz): 1.48-1.63, 1.76-2.02 (1, 5H, 2m,H-3??, 4??, 5??), 2.25-2.35 (1H, m, H-6??alpha), 3.25-3.42 (2H, m, H-2??, 6??beta), 3.79, 3.91 (1H each, d, J = 15.2, 2-8), 3.84 (3H,s, 4?-OCH3), 6.85 (1H, d, J = 8.8, H-6), 6.96 (2H, d, J = 8.5, H-3?, 5?), 7.29-7.36 (1H, m, H-5???), 7.46 (2H, d, J = 8.5, H-2?, 6?),7.78-7.81 (2H, m, H-2, 4???), 8.06 (1H, d, J = 8.8, H-5), 8.51-8.56 (1H, m, H-6???), 8.59-8.66 (1H, m, H-2???). 13C NMR spectrum (100 MHz, CDCl3, delta, ppm): 24.78, 25.78, 35.94, 51.86, 54.49, 55.51, 67.22, 107.33, 113.96, 115.48, 117.24,124.23, 124.26, 124.53, 126.53, 130.11, 135.12, 137.71, 149.17, 151.19, 154.93, 159.47, 162.93, 174.35, 175.69. |