102104-05-2

Upstream product

• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 102104-07-4 2',4'-dihydroxy-3'-((2-hydroxyphenyl)-(1-piperidino)-methyl)-6'-methoxyacetophenone 
• 20939-20-2 2-hydroxyphenyl-bis-1,1-piperidinomethane 
• 5896-17-3 2-(phenylmethoxy)benzaldehyde 
• 90-02-8 salicylaldehyde 
• 100-44-7 benzyl chloride 
• 103633-30-3 2-bromomethylphenyl benzyl ether 
• 3381-87-1 2-benzyloxybenzyl alcohol 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 103633-31-4 5-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone 
• 102056-82-6 2',4'-dihydroxy-3'-(2-hydroxybenzyl)-6'-methoxyacetophenone 

Downstream Products

• 58449-06-2 uravetin 
• 103633-33-6 5'-C-(o-Benzyloxybenzyl)-4'-benzyloxy-6'-hydroxy-2'-methoxychalcone 
• 102104-06-3 (E)-1-[4-Benzyloxy-3-(2-benzyloxy-benzyl)-2-hydroxy-6-methoxy-phenyl]-3-phenyl-propenone 

Relevant academic research and scientific papers

SYNTHESIS OF UVARETIN, AN ANTITUMOUR AND ANTIMICROBIAL FLAVONOID

The flavonoid uvaretin (1-(2,4-dihydroxy-6-methoxy-3-((2-hydroxyphenyl)-methyl)-phenyl)-3-phenyl-1-propanone), known to be active against some tumours and several bacteria, has been synthesized in six steps from 2',4',6'-trimethoxyacetophenone, 2-hydroxybenzaldehyde and benzaldehyde.

Aromatic Benzylation: Part III - Synthesis of Uvaretin, Isouvaretin and Related Nuclear Benzylated Dihydrochalcones

Reaction of 2-O-methylphloroacetophenone (5) with either o-benzyloxybenzyl alcohol (3) in the presence of boron trifluoride etherate and dioxan or with o-benzyloxybenzyl bromide (4) in the presence of methanolic potash affords 5-C-(o-benzyloxybenzyl) derivative (6) and its 3-C-isomer (7).Their orientation has been arrived at from a general behaviour of the chemical shift of chelated hydroxyl group in C-benzylated o-hydroxyacetophenones when C-benzyl group is present ortho or para to the chelated hydroxyl.Partial benzyl ether (9) of 6 and the complete benzyl ether (12) of 7 undergo facile condensation with benzaldehyde in the presence of alkali to give 10 and 13 respectively.These chalcones on hydrogenation in the presence of 10percent Pd-C afford uvaretin (11) and isouvaretin (14) respectively possessing physical characteristics identical with those of the natural samples.A parallel series of reactions starting from resacetophenone (15) provides C-benzylated dihydrochalcones 22 and 25 as analogues of uvaretin and isouvaretin respectively.