ChemicalBook CAS DataBase List cirsimaritin

cirsimaritin synthesis

13synthesis methods

Product Name:cirsimaritin
CAS Number:6601-62-3
Molecular formula:C17H14O6
Molecular Weight:314.29

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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6601-62-3
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Yield: 91%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethanol under 760.051 Torr; for 12 h;

Steps:

19 5-Hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-4Hchromen-4-one (7)
4.1.19
5-Hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-4H-chromen-4-one (7)
To a solution of 23 (100 mg, 0.25 mmol) dissolved in ethanol (30 ml) was added 10% Pd/C (10 mg) with vigorous stirring.
The reaction vessel was then evacuated and the atmosphere replaced with hydrogen.
After 12 h, the reaction mixture was filtered and the filtrate concentrated, the crude material was purified by column chromatography (20% ethyl acetate in petroleum ether) to afford 7 (71 mg, 91% yield) as a yellow solid. ¹H NMR (300 MHz, DMSO-d₆) δ 3.92 (s, 3H, -CH₃), 3.98 (s, 3H, -CH₃), 6.86 (s, 1H, 3-H), 7.52 (s, 1H, 8-H), 7.36 (d, 2H, J = 8.7 Hz, 3',5'-H), 8.15 (d, 2H, J = 8.7 Hz, 2',6'-H), 10.40 (s, 1H, 4'-OH), 13.05 (s, 1H, 5-OH); ESI-MS: m/z 313 [M - H]^-.

References:

Shi, Zhi-Hao;Li, Nian-Guang;Wang, Zhen-Jiang;Tang, Yu-Ping;Dong, Ze-Xi;Zhang, Wei;Zhang, Peng-Xuan;Gu, Ting;Wu, Wen-Yu;Yang, Jian-Ping;Duan, Jin-Ao [European Journal of Medicinal Chemistry,2015,vol. 106,p. 95 - 105]