18096-70-3

Basic information

• Product Name: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one
• Synonyms: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one;(E)-3-dimethylamino-1-(4-methoxyphenyl)prop-2-en-1-one;11C-002;MLS000546311;SMR000169481;ZINC00126223
• CAS NO: 18096-70-3
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• Mol File: 18096-70-3.mol
• Article Data: 91

Chemical Properties

• Melting Point: 92-95℃
• Appearance: /
• CAS DataBase Reference: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one(18096-70-3)
• EPA Substance Registry System: 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one(18096-70-3)

Safety Data

• Hazardous Substances Data: 18096-70-3(Hazardous Substances Data)

Usage

General Description

3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one, also known as DMAP, is a chemical compound with the molecular formula C11H15NO2. It is a yellow crystalline solid that is commonly used as a reagent in organic synthesis. DMAP is an effective catalyst for the acylation of alcohols and amines, as well as the esterification of carboxylic acids. It is also used in the preparation of pharmaceuticals and agrochemicals. DMAP has a wide range of applications in the production of various chemicals and is widely used in the pharmaceutical and agrochemical industries.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 98-86-2 acetophenone 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 20353-93-9 <3-(dimethylamino)-2-azaprop-2-en-1-ylidene> dimethylammonium chloride 
• 20353-93-9 Gold's reagent 
• 506-59-2 N,N-dimethylammonium chloride 
• 34933-41-0 sodium salt of p-methoxybenzoylacetaldehyde 

Downstream Products

• 143621-15-2 (Z)-3-(Hydroxy-methyl-amino)-1-(4-methoxy-phenyl)-propenone 
• 3672-48-8 5-(4-methoxyphenyl)-1,2-oxazole 
• 39812-29-8 <3-chloro-3-(4-methoxyphenyl)-2-propen-1-yliden> dimethyliminium perchlorate 
• 130445-93-1 3-cyano-2-methyl-6-(4-methoxyphenyl)pyridine 
• 4385-63-1 2-(4-methoxyphenyl)-6-methyl-pyridine 
• 1134193-31-9 4-phenyl-1-(o-fluorophenyl)-3-(p-methoxybenzoyl)-1,4-dihydropyridine 
• 1134193-23-9 1-(p-nitrophenyl)-2-phenyl-5-(p-methoxybenzoyl)-1,2-dihydropyridine 
• 1134193-29-5 4-phenyl-1-(p-nitrophenyl)-3-(p-methoxybenzoyl)-1,4-dihydropyridine 
• 1134193-05-7 4-phenyl-1-(m-chlorophenyl)-3-(p-methoxybenzoyl)-1,4-dihydropyridine 
• 1134193-10-4 4-phenyl-1-(p-fluorophenyl)-3-(p-methoxybenzoyl)-1,4-dihydropyridine 
• 14063-79-7 (Z)-3-chloro-3-(4-methoxyphenyl)acrylaldehyde 
• 244625-26-1 (Z)-β-bromo-β-(4-methoxyphenyl)acrolein 
• 1314412-34-4 7-(4-methoxyphenyl)-2-sulfanylidenepyrido[2,3-d]pyrimidine-4-(1H,3H)-one 
• 1446356-30-4 (4-phenyl-1-(p-tolyl)-1,4-dihydropyridine-3,5-diyl)-bis((4-methoxyphenyl)methanone) 

Relevant articles and documents

DDQ-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene

An efficient 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene is developed. It provides a variety of α-alkenylated 1,3-dicarbonyl compounds in moderate to good yields under mild conditions.

Discovery of highly potent tubulin polymerization inhibitors: Design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines

By removing 5-methyl and 6-acetyl groups in our previously reported compound 3, we designed a series of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine derivatives as potential tubulin polymerization inhibitors. Among them, compound 5e displayed low nanomolar antiproliferative efficacy on HeLa cells which was 166-fold higher than the lead analogue 3. Interestingly, 5e displayed significant selectivity in inhibiting cancer cells over HEK-293 (normal human embryonic kidney cells). In addition, 5e dose-dependently arrested HeLa in G2/M phase through the alterations of the expression levels of p-cdc2 and cyclin B1, and caused HeLa cells apoptosis by regulation of expressions of cleaved PARP. Further evidence demonstrated that 5e effectively inhibited tubulin polymerization and was 3-fold more powerful than positive control CA-4. Moreover, molecular docking analysis indicated that 5e overlapped well with CA-4 in the colchicine-binding site. These studies demonstrated that 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine skeleton might be used as the leading unit to develop novel tubulin polymerization inhibitors as potential anticancer agents.

An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes asC4units

An efficient method has been described to synthesize dicarbonyl functionalized 1,3-dienes by cleaving the CC bond of enaminones with cyclopropenes in the presence of a rhodium catalyst. The acetate-substituted cyclopropenes are judiciously chosen as standardC4units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a CC bond cleavage of the enaminone and insertion of a newC(sp2) source with the formation of two C-C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading, ambient temperature, and a neutral reaction solvent.