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

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

Downstream Products

• 90252-91-8 dimethyl 2-hydroxy-4-(2-phenylethenyl)-1,3-benzenedicarboxylate 
• 125404-04-8 2-Amino-4-styryl-pyrimidin 

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.

Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines

A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.

Regioselective Formal [4 + 2] Cycloadditions of Enaminones with Diazocarbonyls through RhIII-Catalyzed C-H Bond Functionalization

A regioselective formal [4 + 2] cycloaddition for the assembly of highly functionalized benzene rings was successfully developed. In this reaction, olefinic C-H bond functionalization/cyclization cascade reaction followed by rearomatization led to the desired molecules in one step under mild reaction conditions. This protocol also displays a broad substrate scope and good tolerance to a wide range of functional groups. Additionally, the potential utility for the synthesis of highly conjugated polybenzenes and diversification of natural products was also demonstrated.