111316-39-3

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 19158-99-7 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 

Downstream Products

• 520-29-6 5,4'-dihydroxy-7-methoxyflavanone 
• 26207-67-0 2-(4-hydroxyphenyl)-5,7-dimethoxychroman-4-one 

Relevant academic research and scientific papers

Asymmetric Synthesis of Sakuranetin-Relevant Flavanones for the Identification of New Chiral Antifungal Leads

Discovery and efficient synthesis of new promising leads have a central role in agrochemical science. Reported herein is the sakuranetin-directed synergistic exploration of an asymmetric synthesis and an antifungal evaluation of chiral flavanones. A new palladium catalytic system with CarOx-type ligands was successfully identified for the highly enantioselective addition of arylboronic acids to chromones. This enabled the facile and programmable construction of a constellation of chiral flavanones (up to 98% yield and 97% ee), in which (R)-pinostrobin was efficiently constructed without laborious protecting/deprotecting operations. Its good performance in asymmetric induction and functional tolerance expanded the chemical space of pharmaceutically important flavanones. The chiral differentiation of flavanones based on antifungal activity and a concise structure-activity relationship model was disclosed and summarized. This synergistic project culminated with acquisition of the naturally unprecedented flavanones with better antifungal potentials than sakuranetin, in which the R-enantiomer of flavanone 54 (EC50 = 0.8 μM) demonstrated better performance than boscalid against Rhizoctonia solani. The novel scaffold and predicted new target compared with the commercial fungicides in the FRAC reinforce the value of further exploration.

Synthesis of 2-Benzylidene-3(2H)-benzofuran-3-ones (Aurones) by Oxidation of 2'-Hydroxychalcones with Mercury(II) Acetate

The reaction of 2'-hydroxychalcones with mercury(II) acetate in acetic acid gives predominantly 2-benzylidene-3(2H)-benzofuran-3-ones (aurones) in 28-62 percent yield accompanied by flavonones in 5-21 percent yield.

PHENOLIC CONSTITUENTS FROM SEEDS OF COPTIS JAPONICA VAR. DISSECTA

In addition to coumarinolignans (cleomiscosin A and aquillochin) and 7,4'-dihydroxy-5-methoxyflavanone, a new dihydrochalcone, 2',4,4'-trihydroxy-6'-methoxydihydrochalcone, was isolated from the seeds of Coptis japonica var. dissecta.The structure of the dihydrochalcone was confirmed by comparison with relevant synthetic samples. - Key Word Index: Coptis japonica var. dissecta; Ranunculaceae; cleomiscosin A; aquillochin; 2',4,4'-trihydroxy-6'-methoxydihydrochalcone; 7,4'-dihydroxy-5-methoxyflavanone.