95-01-2Relevant articles and documents
Preparation of 2,4-dihydroxybenzaldehyde by the Vilsmeier-Haack reaction
Mendelson, Wilford L.,Hayden, Stuart
, p. 603 - 610 (1996)
An efficient synthesis of 2,4-dihydroxybenzaldehyde (1) from resorcinol via the Vilsmeier-Haack reaction has been developed. Either phosphorous oxychloride/DMF or oxalyl chloride/DMF produces 1 in yields of 65-75%. The intermediate formamidinium salts have been characterized.
Hydrogen-bonded supramolecular array in the crystal structure of ethyl 7-hydroxy-2-oxo-2h-chromene-3-carboxylate monohydrate
Galdamez, Antonio,Garcia-Beltran, Olimpo,Cassels, Bruce K.
, p. 546 - 548 (2011)
The crystal structure of ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate monohydrate (1), C12H10O5.H2O, was established by X-ray crystallographic analysis. The molecule of the title compound is essentially planar except for the carboxylate substituent group. The crystal packing supramolecular array arises from hydrogen bonds and intermolecular C-H...O=C contacts of the organic molecules and solvent water molecules, with graph-set descriptor)R24(8), R 21(6), R44(20)and5 (C) motifs. The water molecules are involved as donors and acceptors. The hydrogen bond and intermolecular interaction network is reinforced by stacking of the sheet through π-π interactions.
Coumarin-chalcone hybrids as inhibitors of MAO-B: Biological activity and in silico studies
Moya-Alvarado, Guillermo,Ya?ez, Osvaldo,Morales, Nicole,González-González, Angélica,Areche, Carlos,Nú?ez, Marco Tulio,Fierro, Angélica,García-Beltrán, Olimpo
supporting information, (2021/05/28)
Fourteen coumarin-derived compounds modified at the C3 carbon of coumarin with an α,β-unsaturated ketone were synthesized. These compounds may be designated as chalcocoumarins (3-cinnamoyl-2H-chromen-2-ones). Both chalcones and coumarins are recognized scaffolds in medicinal chemistry, showing diverse biological and pharmacological properties among which neuro-protective activities and multiple enzyme inhibition, including mitochondrial enzyme systems, stand out. The evaluation of monoamine oxidase B (MAO-B) inhibitors has aroused considerable interest as therapeutic agents for neurodegenerative diseases such as Parkinson’s. Of the fourteen chalcocumarins evaluated here against MAO-B, ChC4 showed the strongest activity in vitro, with IC50 = 0.76 ± 0.08 μM. Computational docking, molecular dynamics and MM/GBSA studies, confirm that ChC4 binds very stably to the active rMAO-B site, explaining the experimental inhibition data.
Method for preparing 4-butyl resorcinol
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Paragraph 0015; 0034-0035; 0038-0039, (2020/04/02)
The invention discloses a method for preparing 4-butyl resorcinol. The method comprises the following steps: (1) preparing 2, 4-dihydroxy benzaldehyde; (2) preparing 2, 4-dihydroxy benzylidene acetone; and (3) preparing the 4-butyl resorcinol. The method has the advantages as follows: firstly, raw materials and reagents used in the method are lower in toxicity, safer, cheaper, easier to obtain andconvenient to store, and the raw material cost and operation cost are greatly reduced; secondly, the method has few reaction steps, is convenient to operate, and is easier for large-scale production;and thirdly, high-toxicity three wastes are not generated, environmental pollution is reduced, and the ecological environment is protected. Meanwhile, the yield of the prepared product is high and can reach 90% or above.
Functional group manoeuvring for tuning stability and reactivity: Synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products
Rao, Maddali L. N.,Murty, Venneti N.,Nand, Sachchida
, p. 9415 - 9423 (2017/11/23)
The protecting group manoeuvring as a strategy was applied for tuning the stability and reactivity of 4-(2,2-dibromovinyl)benzene-1,3-diol (12a) and 6-(2,2-dibromovinyl)-2,2-dimethylchroman-7-ol (22) in the domino synthesis of benzofuran-based natural products (1-8). The functional group demands and their impact on the reactivity driven by electronic effects were successfully managed by varying the protecting groups with substituted gem-dibromovinylphenols in domino couplings and triarylbismuth reagents under palladium-catalyzed conditions. This approach paved the way for the synthesis of moracin M (1) and cicerfuran (2), and the first time synthesis of moracin D (3) and moracin E (4) along with chromene-fused benzofuran-based natural products (5-8) in overall good yields.
