515863-74-8

Upstream product

• 844868-35-5 2',4,4'-tris(benzyloxy)-6'-hydroxy-3'-iodochalcone 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 911285-85-3 4,2',4'-tris(benzyloxy)-6'-(methoxymethoxy)-3'-iodochalcone 
• 71386-98-6 2',4'-dihydroxy-6'-(methoxymethoxy)acetophenone 
• 515863-75-9 4,2',4'-tris(benzyloxy)-6'-benzyloxy-3'-iodochalcone 
• 321569-81-7 2',4'-bis(benzyloxy)-3'-iodo-6'-(methoxymethoxy)acetophenone 
• 321569-79-3 2',4'-dihydroxy-3'-iodo-6'-(methoxymethoxy)acetophenone 
• 67052-53-3 4',6'-bis(benzyloxy)-2'-(methoxymethoxy)acetophenone 
• 911285-86-4 1-[6-benzoyloxy-2,4-bis(benzyloxy)-3'-iodophenyl]-2-[4-benzyloxyphenyl]-3,3-dimethyloxypropan-1-one 

Downstream Products

• 844868-36-6 5,7,4'-tris(benzyloxy)-6-(3-hydroxy-3-methyl-1-butynyl)isoflavone 
• 99874-36-9 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 51225-29-7 5,7,4'-triacetoxy-6-(3-methyl-2-butenyl)isoflavone 
• 51225-30-0 erythrinin B 
• 887149-29-3 7,4'-bis(benzoyloxy)-6-(3-hydroxy-3-methylbutyl)-5-tosyloxyisoflavone 
• 887149-30-6 7,4'-bis(benzoyloxy)-6-(3-methyl-2-butenyl)-5-tosyloxyisoflavone 
• 887149-28-2 7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-hydroxy-3-methylbutyl)isoflavone 
• 887149-31-7 7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone 

Relevant academic research and scientific papers

Microwave-assisted regioselective synthesis of natural 6-prenylpolyhydroxyisoflavones and their hydrates with hypervalent iodine reagents

Microwave-assisted oxidative rearrangement of 3′-iodotetraalkoxychalcones with hypervalent iodine such as [hydroxy(tosyloxy)iodo]benzene or [bis(trifluoroacetoxy)iodo]benzene, followed by microwave-mediated hydrolysis and in situ cyclization of the resultant acetals gave 6-iodotrialkoxyisoflavones. Pd(0)-catalyzed coupling reaction of the 6-iodoisoflavones with 2-methyl-3-butyn-2-ol under microwave irradiation gave 6-alkynylisoflavones, whose hydrogenation gave the respective hydrates of wighteone, lupisoflavone and derrubone. Wighteone (1a), lupisoflavone (1b) and derrubone (1c) were obtained by dehydration of their respective hydrates under microwave irradiation.

Regioselective synthesis of 6-prenylpolyhydroxyisoflavone (wighteone) and wighteone hydrate with hypervalent iodine

The oxidative rearrangement of 3′-iodotetraalkoxychalcone with [hydroxyl(tosyloxy)iodo]benzene, followed by cyclization of the resultant acetal gave 6-iodotrialkoxyisoflavone. The coupling reaction of the isoflavone with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone, whose hydrogenation gave wighteone hydrate. Wighteone was synthesized by dehydration of wighteone hydrate. Copyright Taylor & Francis Group, LLC.

Regioselective synthesis of 6-alkyl- and 6-prenylpolyhydroxyisoflavones and 6-alkylcoumaronochromone derivatives

The palladium-catalyzed coupling reaction of 6-iodoisoflavone, prepared from 3′-iodoacetophenone derivative, with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone derivative, which was hydrogenated to give 6-alkylhydroxyisoflavone (luteone hydrate) (2). Dehydration of 2 gave 2′,4′,5,7-tetrahydroxy-6-prenylisoflavone (luteone) (1). Wighteone hydrate (3) was also synthesized from 6-iodotris(benzyloxy)isoflavone in a similar manner. 6-Alkyl-4′5,7-trihydroxy-coumaronochromone (4) was synthesized by oxidative cyclization of 2 with o-chloranil.

Synthesis of isoflavones from 2′-hydroxychalcones using poly[4-(diacetoxy)iodo]styrene or related hypervalent iodine reagent

Isoflavones are synthesized in an one-pot reaction by treating the hypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent) with 2′-benzoyloxychalcones in MeOH. A combined use of (diacetoxyiodo)benzene (DIB)/p-toluenesulfoni