76436-36-7

Upstream product

• 35492-02-5 4,4',6'-trimethoxy-2'-methoxymethoxy-trans-chalcone epoxide 
• 16546-01-3 ethyl 3-(4-methoxyphenyl)-2,3-epoxypropionate 
• 108-73-6 3,5-dihydroxyphenol 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 76436-33-4 (+/-)-ethyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2,4,6-trihydroxyphenyl)propionate 
• 74-88-4 methyl iodide 
• 76436-35-6 (2R,3R)-2-Hydroxy-3-(4-methoxy-phenyl)-3-(2,4,6-trihydroxy-phenoxy)-propionic acid ethyl ester 
• 76436-33-4 (2R,3R)-2-Hydroxy-3-(4-methoxy-phenyl)-3-(2,4,6-trihydroxy-phenyl)-propionic acid ethyl ester 
• 500-99-2 3,5-dimethoxyphenol 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 76436-22-1 2-hydroxy-3-(4-methoxyphenyl)-3-(2-hydroxy-4,6-dimethoxyphenyl)-4',6'-dimethoxy-2'-methoxymethoxypropiophenone 

Downstream Products

• 123731-50-0 5,7-dimethoxy-3-(4-methoxyphenyl)-2H-1-benzopyran-2-one 
• 76451-12-2 Toluene-4-sulfonic acid (3S,4S)-5,7-dimethoxy-4-(4-methoxy-phenyl)-2-oxo-chroman-3-yl ester 
• 76436-37-8 cis-3-acetoxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one 
• 76451-12-2 Toluene-4-sulfonic acid (3R,4S)-5,7-dimethoxy-4-(4-methoxy-phenyl)-2-oxo-chroman-3-yl ester 
• 76436-37-8 trans-3-acetoxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one 

Relevant academic research and scientific papers

Reactions of Methyl threo-2-Acetoxy-3-chloro-3-(4-methoxyphenyl)propanoate and Methyl cis-2,3-Epoxy-3-(4-methoxyphenyl)propanoate with 3,5-Dimethoxyphenol: Potential Routes to Flavan-3-ols

Attempted syntheses of flavan-3-ols by reaction of either methyl threo-2-acetoxy-3-chloro-3-(4-methoxyphenyl)propanoate (3) or methyl cis-2,3-epoxy-3-(4-methoxyphenyl)propanoate (14) with 3,5-dimethoxyphenol failed to give the required aryl ethers.Products usually were derived from C-alkylation of the electron-rich phenol although reaction of the chloro acetate (3) with the phenoxide ion gave the furanone (5).The single-crystal X-ray structures of methyl 4-hydroxy-3-(4-methoxyphenyl)-2-(4-methoxyphenylmethyl)-5-oxo-2,5-dihydrofuran-2-carboxylate and cis-3-hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-2-one have been determined.

Some Novel Photochemical and Related Aryl Couplings and Migrations in Flavonoid Synthesis

2'-Methoxymethoxy-4,4',6'-trimethoxychalcone epoxide couples at the β-position with 3,5-dimethoxyphenol under photolytic conditions to form isomeric 1,3,3-triaryl-2-hydroxypropiophenones.These propiophenones are subject to photo-induced α-ketol rearrangements yielding isomeric 1-hydroxypropan-2-ones.Together these serve as useful synthetic intermediates for 4-arylflavan-3-ones and novel 2-hydroxy-2-arylbenzylbenzofuran-3(2H)-ones and 4-aryl-3-hydroxy-3,4-cis-dihydrocoumarins.The same epoxide reacts ionically under ambient conditions with 2,4,6-trihydroxybenzoic acid to afford a 3-O-benzoylpropiophenone intermediate, which provides novel access to isoflavones in high overall yield.Analogous coupling of phloroglucinol to epoxycinnamates gives diastereoisomeric 3,3-diaryl-2-hydroxypropionates which serve as precursors for 3,4-trans- and 3,4-cis-4-aryl-3-hydroxydihydrocoumarins and thence for 3-aryl- and 3-hydroxycoumarins.