94190-89-3

Basic information

• Product Name: 1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone
• Synonyms: 1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone
• CAS NO: 94190-89-3
• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.22586
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 94190-89-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 128°C
• Appearance: /
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone(94190-89-3)
• EPA Substance Registry System: 1-(2,3-Dihydroxy-4,6-diMethoxyphenyl)-1-propanone(94190-89-3)

Safety Data

• Hazardous Substances Data: 94190-89-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

1-(2,3-Dihydroxy-4,6-dimethoxyphenyl)-1-propanone is a reactant used in the preparation of Stigmatellin A (S686780).

Preparation

Preparation by Fries rearrangement of 1,2-dihydroxy-3,5-dimethoxybenzene dipropionate with aluminium chloride in methylene chloride at r.t. for 3 h (94%).

Upstream product

• 89880-48-8 1-(2,3,4,6-tetramethoxyphenyl)propan-1-one 
• 5333-45-9 1,2,3,5-tetramethoxybenzene 
• 293743-95-0 methyl 7-hydroxy-2-phenylbenzo[d][1,3]dioxole-5-carboxylate 
• 293743-98-3 7-methoxy-2-phenyl-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 293744-00-0 7-methoxy-2-phenyl-benzo[1,3]dioxol-5-ol 
• 293743-99-4 7-methoxy-2-phenyl-benzo[1,3]dioxole-5-carbaldehyde 
• 293744-01-1 4,6-dimethoxy-2-phenyl-benzo[1,3]dioxole 
• 94190-87-1 1-(2-Hydroxy-4,6-dimethoxy-3-propionylphenyl)-1-propanone 
• 99-24-1 methyl galloate 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 21128-11-0 1,2-dihydroxy-3,5-dimethoxybenzene 
• 500-99-2 3,5-dimethoxyphenol 
• 293744-02-2 propionic acid 2,4-dimethoxy-6-propionyloxy-phenyl ester 
• 94190-88-2 Propionic acid 2-hydroxy-4,6-dimethoxy-3-propionylphenyl ester 

Downstream Products

• 276690-22-3 (2R,3S,4S,5S)-7-[5,7-dimethoxy-8-methoxymethoxy-3-methyl-4-oxo-4H-2-chromenyl]-2,4-dimethoxy-3,5-dimethylheptanol 
• 91682-96-1 stigmatellin A 
• 276690-20-1 (4S,5S,6S,7R)-8-Benzyloxy-5,7-dimethoxy-4,6-dimethyloctanoic acid 3,5-dimethoxy-2-methoxymethoxy-6-propionylphenyl ester 
• 276690-21-2 2-[(3S,4S,5S,6R)-7-Benzyloxy-4,6-dimethylheptyl]-5,7-dimethoxy-8-methoxymethoxy-3-methyl-4H-1-benzopyran-4-one 
• 293743-94-9 (2S,3S,4S)-6-(8-Benzyloxy-5,7-dimethoxy-3-methyl-4-oxo-4H-chromen-2-yl)-3-methoxy-2,4-dimethyl-hexanal 
• 293744-14-6 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one 
• 293743-92-7 (4S,5S,6R)-5-Methoxy-4,6-dimethyl-7-triisopropylsilanyloxy-heptanoic acid 2-benzyloxy-3,5-dimethoxy-6-propionyl-phenyl ester 
• 293744-13-5 8-Benzyloxy-5,7-dimethoxy-2-((3S,4S,5R)-4-methoxy-3,5-dimethyl-6-triisopropylsilanyloxy-hexyl)-3-methyl-chromen-4-one 
• 293744-03-3 1-(3-benzyloxy-2-hydroxy-4,6-dimethoxy-phenyl)-propan-1-one 
• 276690-11-0 1-[2-hydroxy-4,6-dimethoxy-3-(methoxymethoxy)phenyl]propan-1-one 

Relevant articles and documents

Formal total synthesis of stigmatellin A

An efficient and stereoselective approach for the formal total synthesis of Stigmatellin A has been described. The key steps involved in this synthesis are desymmetrization of the bicyclic olefin to introduce two methyl and two hydroxyl chiral centers, Fr

Toward a total synthesis of stigmatellin; Obtention of an advanced fragment from gallic acid

Treatment by a base, then an acid, of the ester 3, which was prepared by starting from gallic acid 7a, afforded the chromone 6c, whose Swern oxidation, followed by condensation of the resulting aldehyde 6a with the trienyl lithium derivative 13b and methyl iodide, furnished products isomeric with, but not strictly identical to, an authentic sample of O-benzyl stigmatellin 1c. (C) 2000 Elsevier Science Ltd.