6302-60-9

Basic information

• Product Name: 4-(3,4-dimethoxyphenyl)butan-2-one
• Synonyms: 4-(3,4-dimethoxyphenyl)butan-2-one
• CAS NO: 6302-60-9
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• Mol File: 6302-60-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 301.2°C at 760 mmHg
• Flash Point: 126.9°C
• Appearance: /
• Density: 1.039g/cm³
• Vapor Pressure: 0.00107mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: 4-(3,4-dimethoxyphenyl)butan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,4-dimethoxyphenyl)butan-2-one(6302-60-9)
• EPA Substance Registry System: 4-(3,4-dimethoxyphenyl)butan-2-one(6302-60-9)

Safety Data

• Hazardous Substances Data: 6302-60-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16O3/c1-9(13)4-5-10-6-7-11(14-2)12(8-10)15-3/h6-8H,4-5H2,1-3H3

Upstream product

• 51842-87-6 3-(3,4-dimethoxy-phenyl)-propionyl chloride 
• 75-24-1 trimethylaluminum 
• 77-78-1 dimethyl sulfate 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 74-88-4 methyl iodide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 61914-52-1 1-(3,4-dimethoxyphenyl)-5-hydroxydecan-3-one 
• 2107-70-2 3,4-methoxycinnamic acid 
• 75-16-1 methylmagnesium bromide 
• 23513-14-6 (+/-)-[6]-gingerol 
• 60234-90-4 4-(3,4-dimethoxy-phenyl)-but-3-en-2-one 
• 153993-01-2 tert-Butyl-[3-(3,4-dimethoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane 
• 1833-53-0 2-(Trimethylsilyloxy)propene 

Downstream Products

• 61871-73-6 methylzingerone trimethylsilyl ether 
• 81580-10-1 5-{2-[3-(3,4-Dimethoxy-phenyl)-1-methyl-propylamino]-1-hydroxy-ethyl}-2-hydroxy-benzamide 
• 91998-04-8 (+/-)-di-O-methyl hexahydrocurcumin 
• 77741-94-7 [3-(3,4-Dimethoxy-phenyl)-1-methyl-propyl]-(6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine 
• 153993-01-2 tert-Butyl-[3-(3,4-dimethoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane 
• 57507-12-7 5-(3,4-Dimethoxy-phenyl)-3-methyl-pent-1-yn-3-ol 
• 188476-32-6 4-((E)-4-Allyloxy-3-methyl-but-3-enyl)-1,2-dimethoxy-benzene 
• 79622-76-7 3,4-Dimethoxy-(3'-hydroxybutyl)-benzol 
• 75-25-2 Bromoform 
• 2107-70-2 3,4-methoxycinnamic acid 
• 860518-51-0 1,3,5-tris-(3,4-dimethoxy-phenethyl)-benzene 
• 93-07-2 Veratric acid 
• 838846-23-4 2-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-methyl-pent-4-enal 
• 181222-25-3 4-(3-azidobutyl)-1,2-dimethoxybenzene 

Relevant articles and documents

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides

We report our studies on the development of a catalytic cycloisomerization of 2,2-disubstituted neopentylic epoxides to produce highly substituted tetralins and chromanes. Termination of the sequence occurs via Friedel-Crafts-type alkylation of the remote (hetero)arene linker. The transformation is efficiently promoted by sulfuric acid and proceeds best in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as the solvent. Variation of the substitution pattern provided detailed insights into the migration tendencies and revealed a competing disproportionation pathway of dihydronaphthalenes.

Structure-Activity Relationships of 6- and 8-Gingerol Analogs as Anti-Biofilm Agents

Pseudomonas aeruginosa is a causative agent of chronic infections in immunocompromised patients. Disruption of quorum sensing circuits is an attractive strategy for treating diseases associated with P. aeruginosa infection. In this study, we designed and synthesized a series of gingerol analogs targeting LasR, a master regulator of quorum sensing networks in P. aeruginosa. Structure-activity relationship studies showed that a hydrogen-bonding interaction in the head section, stereochemistry and rotational rigidity in the middle section, and optimal alkyl chain length in the tail section are important factors for the enhancement of LasR-binding affinity and for the inhibition of biofilm formation. The most potent compound 41, an analog of (R)-8-gingerol with restricted rotation, showed stronger LasR-binding affinity and inhibition of biofilm formation than the known LasR antagonist (S)-6-gingerol. This new LasR antagonist can be used as an early lead compound for the development of anti-biofilm agents to treat P. aeruginosa infections.