31273-58-2

Basic information

• Product Name: Ethanone, 1-(3,4-dihydro-7-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-
• CAS NO: 31273-58-2
• Molecular Formula: C13H16O3
• Molecular Weight: 220.268
• Mol File: 31273-58-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-(3,4-dihydro-7-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(3,4-dihydro-7-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-(31273-58-2)
• EPA Substance Registry System: Ethanone, 1-(3,4-dihydro-7-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-(31273-58-2)

Safety Data

• Hazardous Substances Data: 31273-58-2(Hazardous Substances Data)

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 14125-75-8 2,3,4,6-tetra-O-benzoyl-D-hydroxyglucal 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose 
• 27305-54-0 8,8-Dimethyl-2-phenyl-7,8-dihydro-6H-pyrano[3,2-g]chromen-4-one 
• 86978-00-9 2-(4-Methoxy-phenyl)-8,8-dimethyl-7,8-dihydro-6H-pyrano[3,2-g]chromen-4-one 
• 135940-06-6 2-(3,4-Dimethoxy-phenyl)-8,8-dimethyl-7,8-dihydro-6H-pyrano[3,2-g]chromen-4-one 
• 19013-03-7 6-acetyl-7-hydroxy-2,2-dimethyl-1H-chromene 
• 52601-07-7 2'-hydroxy-6,6-dimethyl-4,5-dihydropyrano<2,3:4',5'>chalcone 
• 118267-01-9 1-(7-hydroxy-2,2-dimethylchroman-6-yl)-3-(4-hydroxyphenyl)propenone 
• 88055-36-1 7-Hydroxy-8-(4'-methoxyphenyl)-2,2-dimethyl-3,4-dihydro-2H,6H-benzo<1,2-b:5,4-b'>dipyran-6-one 
• 143885-61-4 7-hydroxy-6-(4'-methoxy)cinnamoyl-3,4-dihydro-2,2-dimethyl-2H-benzo(1,2b)pyran 
• 82448-49-5 6-Acetyl-7-benzoyloxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran 
• 148180-71-6 2'-hydroxy-2,4-dimethoxy-6,6-dimethyl-4,5-dihydropyrano<2,3:4',5'>chalcone 
• 148180-70-5 2'-hydroxy-2,3-dimethoxy-6,6-dimethyl-4,5-dihydropyrano<2,3:4',5'>chalcone 
• 51619-67-1 6-chromane-O-7-flavanone 

Relevant articles and documents

Synthesis of isobavachalcone and some organometallic derivatives

Isobavachalcone [2′,4,4′-trihydroxy-3′-(3″-methyl- 2″-butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of 190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium-catalysed Stille coupling of 3-iodo-2,4-bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen-Schmidt condensation with 4-(methoxymethoxy)benzaldehyde to form the triply MOM-protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy) benzaldehyde used in the Claisen-Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5-formylcyclopentadienyl) (η4-tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.