82606-90-4

Basic information

• Product Name: 1-(DIMETHYLAMINO)-5-PHENYL-1,4-PENTADIEN-3-ONE
• Synonyms: 1-(DIMETHYLAMINO)-5-PHENYL-1,4-PENTADIEN-3-ONE;(1E,4E)-1-(Dimethylamino)-5-phenylpenta-1,4-dien-3-one
• CAS NO: 82606-90-4
• Molecular Formula: C₁₃H₁₅NO
• Molecular Weight: 201.26
• Mol File: 82606-90-4.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(DIMETHYLAMINO)-5-PHENYL-1,4-PENTADIEN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(DIMETHYLAMINO)-5-PHENYL-1,4-PENTADIEN-3-ONE(82606-90-4)
• EPA Substance Registry System: 1-(DIMETHYLAMINO)-5-PHENYL-1,4-PENTADIEN-3-ONE(82606-90-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 82606-90-4(Hazardous Substances Data)

Usage

Physical State

Solid

Color

Yellow to orange-brown

Odor

Distinct

Primary Use

Production of pharmaceuticals

Secondary Use

Reagent in organic chemistry

Biological Activity

Potential (interest in medicinal chemistry)

Environmental Impact

Suspected environmental toxin

Aquatic Organisms

Potentially harmful effects

Handling and Disposal

Caution required

Upstream product

• 82606-85-7 (1E,4Z)-1-phenyl-5-hydroxypenta-1,4-dien-3-one 
• 124-40-3 dimethyl amine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 1896-62-4 (E)-benzalacetone 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 100-52-7 benzaldehyde 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 1186-70-5 bis(dimethylamino)methoxymethane 

Downstream Products

• 90252-91-8 dimethyl 2-hydroxy-4-(2-phenylethenyl)-1,3-benzenedicarboxylate 
• 125404-04-8 2-Amino-4-styryl-pyrimidin 
• 1448799-01-6 (E)-1-(5-hydroxy-6-methoxybenzofuran-3-yl)-3-phenylprop-2-en-1-one 

Relevant articles and documents

Synthesis, C-H bond functionalisation and cycloadditions of 6-styryl-1,2-oxathiine 2,2-dioxides

A series of 6-styryl-1,2-oxathiine 2,2-dioxides have been efficiently obtained by a two-step protocol from readily available (1E,4E)-1-(dimethylamino)-5-arylpenta-1,4-dien-3-ones involving a regioselective sulfene addition and subsequent Cope elimination. Pd-Mediated direct C-H bond functionalisation of the 6-styryl-1,2-oxathiine 2,2-dioxides and a wider selection of 5,6-diaryl substituted 1,2-oxathiine 2,2-dioxides proceeded smoothly to afford C-3 (hetero)aryl substituted analogues and the results are contrasted with those of a complementary bromination - Suzuki cross-coupling sequence. Whilst the cycloaddition of benzyne, derived fromin situfluoride initiated decomposition of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, to the substituted 1,2-oxathiine 2,2-dioxides resulted in low yields of substituted naphthalenes, the addition of 4-phenyl-1,2,4-triazoline-3,5-dione to the 6-styryl-1,2-oxathiine 2,2-dioxides afforded novel 5,9-dihydro-1H-[1,2]oxathiino[5,6-c][1,2,4]triazolo[1,2-a]pyridazine-1,3(2H)-dione 8,8-dioxides through a silica-mediated isomerisation of the initial [4 + 2] adducts.

A copper-catalyzed three component reaction of aryl acetylene, sulfonyl azide and enaminone to form iminolactone via 6π electrocyclization

We developed a copper-catalyzed three component reaction of aryl acetylene, enaminone and sulfonyl azide to construct iminolactone via a cascade process involving copper-catalyzed alkyne-azide cycloaddition (CuAAC), Michael addition of metalated ketenimin

Rh(III)-Catalyzed Enaminone-Directed Alkenyl C-H Activation for the Synthesis of Salicylaldehydes

A Rh(III)-catalyzed enaminone-directed alkenyl C-H coupling with alkynes for the synthesis of salicylaldehyde derivatives is reported. This represents a unique example of benzene ring framework formation through a transition-metal-catalyzed, directed C-H activation strategy. The two incorporated reactive functionalities, aldehyde and hydroxy groups, provide convenient synthetic handles for further structural elaboration.