32396-83-1

Basic information

• Product Name: 3(2H)-Benzofuranone, 2-[(3,4-dimethoxyphenyl)methylene]-6-hydroxy-
• CAS NO: 32396-83-1
• Molecular Formula: C17H14O5
• Molecular Weight: 298.295
• Mol File: 32396-83-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 3(2H)-Benzofuranone, 2-[(3,4-dimethoxyphenyl)methylene]-6-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 3(2H)-Benzofuranone, 2-[(3,4-dimethoxyphenyl)methylene]-6-hydroxy-(32396-83-1)
• EPA Substance Registry System: 3(2H)-Benzofuranone, 2-[(3,4-dimethoxyphenyl)methylene]-6-hydroxy-(32396-83-1)

Safety Data

• Hazardous Substances Data: 32396-83-1(Hazardous Substances Data)

Upstream product

• 6272-26-0 6-hydroxybenzofuran-3-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 108-46-3 recorcinol 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 104236-80-8 2′,4′-dihydroxy-3,4-dimethoxychalcone 

Downstream Products

• 1005324-89-9 2-(3,4-dihydroxybenzyl)-6-hydroxybenzofuran-3(2H)-one 

Relevant articles and documents

Efficient synthesis of aurone Mannich bases and evaluation of their antineoplastic activity in PC-3 prostate cancer cells

Abstract: An efficient method for regioselective synthesis of C-7 Mannich bases of 6-hydroxyaurones was accomplished by the N,N-dialkylaminomethylation using aminals prepared from dimethylamine, dipropylamine, bis(2-methoxyethyl)amine, N-methylbutylamine, N-methylbenzylamine, morpholine, piperidine, and 1-methylpiperazine. Further transformation of 7-(N,N-dialkylamino)methyl group in these aurones led to formation of C-7 acetoxymethyl and methoxymethyl derivatives of 6-hydroxyaurones, some of which showed promising inhibition of PC-3 prostate cancer cell proliferation in the high nanomolar to low micromolar range that exceeded that of cisplatin. Graphical abstract: Compound 12c (R3 = Ac, Ar = 3,4-OMePh) displays 75% inhibition of PC-3 prostate cancer cells proliferation at 300 nM concentration.[Figure not available: see fulltext.]

Synthesis of Flavonoid Derivatives of Cytisine. 5. Aminomethylation of 6-Hydroxyaurones

Aminomethylation of 6-hydroxy- and 6-hydroxy-7-methylaurones by the alkaloid cytisine was studied. It was shown that the aminomethylation of the 6-hydroxyaurones occurred at the 7-position of the benzofuran ring and at the 5-position if the 7-position was occupied.

Synthesis and properties of 2-benzylidene-8,9-dihydro-7H-furo[2,3-f][1,3]benzoxazin-3(2H)-one derivatives

[Figure not available: see fulltext.] Aminomethylation of 6-hydroxyaurones with primary amines was used to synthesize 2-benzylidene-8,9-dihydro-7H-furo[2,3-f][1,3]-benzoxazin-3(2H)-one derivatives, while opening of 1,3-oxazine ring in the presence of acid gave secondary amines containing a 6-hydroxyaurone moiety. Acetylation of 2-benzylidene-8,9-dihydro-7H-furo[2,3-f][1,3]benzoxazin-3(2H)-ones was also accompanied by opening of 1,3-oxazine ring.