20767-18-4

Basic information

• Product Name: Benzene, 4-[2-(3,5-dimethoxyphenyl)ethenyl]-1,2-dimethoxy-
• Synonyms: 3,4,3',5'-tetramethoxy-stilbene;Piceatannol-methylether;3,4,3',5'-Tetramethoxystilben;3,3',4,5'-Tetramethoxystilben;3,4,3',4'-tetramethoxystilbene;3,4,3',5'-Tetramethoxy-stilben
• CAS NO: 20767-18-4
• Molecular Formula: C18H20O4
• Molecular Weight: 300.354
• Mol File: 20767-18-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzene, 4-[2-(3,5-dimethoxyphenyl)ethenyl]-1,2-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 4-[2-(3,5-dimethoxyphenyl)ethenyl]-1,2-dimethoxy-(20767-18-4)
• EPA Substance Registry System: Benzene, 4-[2-(3,5-dimethoxyphenyl)ethenyl]-1,2-dimethoxy-(20767-18-4)

Safety Data

• Hazardous Substances Data: 20767-18-4(Hazardous Substances Data)

Upstream product

• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 397333-50-5 (3,5-dimethoxy-benzyl)phosphonic acid dimethyl ester 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 667458-79-9 3,5-dimethoxybenzyl 3,5-bis(trifluoromethyl)phenyl sulfone 
• 4339-71-3 piceatannol 
• 77-78-1 dimethyl sulfate 
• 863560-56-9 [3,5-bis(trifluoromethyl)phenyl] 3,5-dimethoxybenzyl sulfide 

Downstream Products

• 22318-87-2 3,5,4',5'-tetramethoxydihydrostilbene 
• 4339-71-3 piceatannol 
• 22318-80-5 Dihydropiceatannol 
• 22318-88-3 3,4,3',5'-Tetramethoxy-2',6'-diioddibenzyl 

Relevant articles and documents

Synthesis method of piceatannol

The present invention provides a synthesis method of piceatannol. The method comprises the following steps: reacting 3,5-dimethoxybenzyl alcohol with phosphorus oxychloride to obtain 3,5-dimethoxybenzyl chloride; adding the obtained 3,5-dimethoxybenzyl ch

3,5-Bis(trifluoromethyl)phenyl sulfones in the direct Julia-Kocienski olefination

3,5-Bis(trifluoromethyl)phenyl (BTFP) sulfones 7 have been employed in the Julia-Kocienski olefination reaction with carbonyl compounds. Sulfones 7 are readily prepared in high yields (64-97%) from commercially available 3,5-bis(trifluoromethyl)thiophenol through an alkylation/oxidation two-step sequence. The stability of metalated BTFP sulfones has been studied and compared with heteroaryl benzothiazol-2-yl (BT), 1-phenyl-1H-tetrazol-5-yl (PT), and 1-tert-butyl-1H-tetrazol-5-yl (TBT) sulfones 9-11 under different reaction conditions. The Julia-Kocienski olefination between alkyl BTFP sulfones 7 and a wide variety of aldehydes affords the corresponding 1,2-disubstituted alkenes and dienes in good yields and stereoselectivities. This one-pot protocol can be performed using KOH at room temperature or the phosphazene bases P2-Et and P4-t-Bu at -78 °C or rt and has been successfully used in a high-yielding and stereoselective synthesis of various methoxylated stilbenes such as trimethylated resveratrol. These new reaction conditions for the Julia-Kocienski olefination reaction have been also studied with BT, PT, and TBT sulfones, giving poorer results. Methylenation of aliphatic and aromatic aldehydes, ketones, and 1,2-dicarbonyl compounds is carried out through the modified Julia olefination using BTFP methyl sulfone 7d to give terminal alkenes and dienes. Mechanistic studies of the olefination reaction between benzyl BTFP sulfone 7a and aromatic aldehydes performed by KOH-induced Smiles rearrangement of stereodefined syn- and anit-β-hydroxyalkyl BTFP sulfones indicate that the stereocontrol of the reaction is determined in the elimination step. 2005 American Chemical Society.