57193-17-6

Basic information

• Product Name: 2-(3,4-DIMETHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE
• Synonyms: 2-(3,4-DIMETHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE;4,5-dihydro-2-(3,4-dimethoxyphenyl)-4,4-dimethyl-oxazol;2-(3,4-DIMETHOXYPHENYL)-4,4-DIMETHYL-2-OXAZOLINE
• CAS NO: 57193-17-6
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.28
• Mol File: 57193-17-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 335.4°Cat760mmHg
• Flash Point: 127.9°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.000233mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: 2-(3,4-DIMETHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-DIMETHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE(57193-17-6)
• EPA Substance Registry System: 2-(3,4-DIMETHOXYPHENYL)-4,4-DIMETHYL-4,5-DIHYDRO-1,3-OXAZOLE(57193-17-6)

Safety Data

• Hazardous Substances Data: 57193-17-6(Hazardous Substances Data)

Usage

Chemical class

Oxazole class of molecules

Molecular structure

Five-membered heterocyclic ring containing one oxygen and one nitrogen atom

Substituents

3,4-Dimethoxyphenyl and 4,4-dimethyl groups

Dihydro classification

4,5-Dihydro

Potential pharmaceutical applications

Interaction with biological systems due to methoxy groups

Stability and structural properties

Contributed by the dimethyl group

Research interest

Unique structure and potential reactivity in the fields of medicinal chemistry and drug development

InChI:InChI=1/C13H17NO3/c1-13(2)8-17-12(14-13)9-5-6-10(15-3)11(7-9)16-4/h5-7H,8H2,1-4H3

Upstream product

• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 100098-63-3 3,4-dimethoxy-N-(2-hydroxy-1,1-dimethylethyl) benzamide 

Downstream Products

• 115802-62-5 4,5-dihydro-2-<3,4-dimethoxy-2-(4'-methoxybenzyl)phenyl>-4,4-dimethyloxazole 
• 172657-07-7 1-(2-Fluoro-3,4-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline 
• 115831-71-5 3,4-dihydro-3-hydroxy-5,6-dimethoxy-4-(4'-methoxyphenyl)-2-methylisoquinolin-1(2H)-one 
• 115802-60-3 5,6-dimethoxy-4-(4'-methoxyphenyl)-2-methylisoquinolin-1(2H)-one 
• 115802-59-0 N-methyl-3,4-dimethoxy-2-(4'-methoxybenzyl)benzamide 
• 115888-85-2 (+/-)-latifine dimethyl ether 
• 115802-58-9 3,4-dimethoxy-2-(4'-methoxybenzyl)benzoic acid 
• 172657-12-4 1-(3,4-Dimethoxy-2,5,6,-trifluorophenyl)-4,4-dimethyl-2-oxazoline 
• 172657-10-2 1-(2,6-Difluoro-4,5-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline 
• 172657-05-5 2,5,6-Trifluoroveratraldehyde 
• 130131-80-5 Bis-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-4,5-dimethoxy-phenyl]-methanone 
• 133348-10-4 2-(2-Allyl-4,5-dimethoxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 4741-58-6 4,5-dimethoxyisobenzofuran-1(3H)-one 
• 133341-99-8 2-(3,4-Dimethoxy-2,6-dimethyl-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole 

Relevant articles and documents

Accelerating effect of meta substituents in the ester-mediated nucleophilic aromatic substitution reaction

The ester-mediated nucleophilic aromatic substitution (SNAr) reaction of 2-methoxybenzoic ester 1 with Grignard reagents 11 is greatly accelerated by introduction of a methoxy or halo substituent at the 3-position of the benzoate ring (7-10). The substituent effects of these groups at the 3-position are compared with those at the 5-position to suggest that the activation mechanism of the methoxy substituent is different from that of the halo substituent; the ligating ability of the 3-methoxy group plays a crucial role in enhancing the reactivity of the 2-methoxy moiety, while the electron-withdrawing ability is more important in the case of the halo groups. It has also been found that introduction of an additional methoxy substituent at the meta-position (33, 34) enables the SNAr methoxy-displacement reaction even at the para-position to the ester activator. The accelerating effect of the 3-bromo substituent is advantageously utilized for regioselective allylation of 3-bromo-2,6-dimethoxybenzoic ester 55 at the 2-position to provide an easy access to a multisubstituted naphthol 59, which is a key compound for the syntheses of michellamines A-C and the related naphthylisoquinoline alkaloids.

BENZ-FUSED LACTONES I. SYNTHESIS OF 3-METHYL-1(3H)-ISOBENZOFURANONES

Unsubstituted and 3-alkyl substituted 1(3H)-isobenzofuranones are readily prepared in good yields via ortho-metallation of appropriate aromatics.