321569-79-3

Basic information

• Product Name: Ethanone, 1-[2,4-dihydroxy-3-iodo-6-(methoxymethoxy)phenyl]-
• CAS NO: 321569-79-3
• Molecular Formula: C10H11IO5
• Molecular Weight: 338.099
• Mol File: 321569-79-3.mol

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-[2,4-dihydroxy-3-iodo-6-(methoxymethoxy)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-[2,4-dihydroxy-3-iodo-6-(methoxymethoxy)phenyl]-(321569-79-3)
• EPA Substance Registry System: Ethanone, 1-[2,4-dihydroxy-3-iodo-6-(methoxymethoxy)phenyl]-(321569-79-3)

Safety Data

• Hazardous Substances Data: 321569-79-3(Hazardous Substances Data)

Upstream product

• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 67052-53-3 4',6'-bis(benzyloxy)-2'-(methoxymethoxy)acetophenone 
• 71386-98-6 2',4'-dihydroxy-6'-(methoxymethoxy)acetophenone 

Downstream Products

• 887149-31-7 7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-methyl-2-butenyl)isoflavone 
• 887149-28-2 7,4'-bis(benzoyloxy)-5-hydroxy-6-(3-hydroxy-3-methylbutyl)isoflavone 
• 887149-30-6 7,4'-bis(benzoyloxy)-6-(3-methyl-2-butenyl)-5-tosyloxyisoflavone 
• 887149-29-3 7,4'-bis(benzoyloxy)-6-(3-hydroxy-3-methylbutyl)-5-tosyloxyisoflavone 
• 887149-27-1 4,2',4'-tris(benzyloxy)-6'-hydroxy-3'-iodochalcone 
• 51225-30-0 erythrinin B 
• 51225-29-7 5,7,4'-triacetoxy-6-(3-methyl-2-butenyl)isoflavone 
• 99874-36-9 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 515863-74-8 4',5,7-tris(benzyloxy)-6-iodoisoflavone 
• 911285-86-4 1-[6-benzoyloxy-2,4-bis(benzyloxy)-3'-iodophenyl]-2-[4-benzyloxyphenyl]-3,3-dimethyloxypropan-1-one 
• 911285-85-3 4,2',4'-tris(benzyloxy)-6'-(methoxymethoxy)-3'-iodochalcone 
• 515863-75-9 4,2',4'-tris(benzyloxy)-6'-benzyloxy-3'-iodochalcone 
• 844868-36-6 5,7,4'-tris(benzyloxy)-6-(3-hydroxy-3-methyl-1-butynyl)isoflavone 
• 321569-83-9 (E)-1-(2,4-Bis-benzyloxy-3-iodo-6-methoxymethoxy-phenyl)-3-(2,4-bis-benzyloxy-phenyl)-propenone 

Relevant articles and documents

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.

Regioselective synthesis of prenylisoflavones: Syntheses of luteone and luteone hydrate

The palladium-catalyzed coupling reaction of 6-iodoisoflavone, prepared from 3′-iodoacetophenone derivative, with 2-methyl-3-butyn-2-ol gave the 6-alkynylisoflavone derivative, which was hydrogenaied to give the 6-alkylhydroxyisoflavone (luteone hydrate)