58369-45-2

Basic information

• Product Name: 4-Pentene-1,3-dione, 1,5-diphenyl-, (E)-
• CAS NO: 58369-45-2
• Molecular Formula: C17H14O2
• Molecular Weight: 250.297
• Mol File: 58369-45-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 4-Pentene-1,3-dione, 1,5-diphenyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentene-1,3-dione, 1,5-diphenyl-, (E)-(58369-45-2)
• EPA Substance Registry System: 4-Pentene-1,3-dione, 1,5-diphenyl-, (E)-(58369-45-2)

Safety Data

• Hazardous Substances Data: 58369-45-2(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 93-91-4 1-phenylbutan-1,3-dione 
• 100-52-7 benzaldehyde 
• 60-29-7 diethyl ether 
• 2757-04-2 phenyl cinnamate 
• 328012-09-5 (E)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenylprop-2-en-1-one 
• 37845-36-6 1,5-diphenyl-1-penten-4-yn-3-one 
• 932-90-1 Benzaldoxime 
• 98-88-4 benzoyl chloride 
• 1896-62-4 (E)-benzalacetone 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 22422-16-8 (E)-1-bromo-4-phenylbut-3-en-2-one 
• 63468-90-6 phenylglyoxylic acid potassium salt 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 69577-41-9 (E)-1,6-diphenylhex-5-ene-1,4-dione 

Relevant articles and documents

Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation

We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.

Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones

A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.

MgBr2·OEt2-promoted coupling of ketones and activated acyl donors via soft enolization: A practical synthesis of 1,3-diketones

Ketones undergo soft enolization and acylation on treatment with MgBr 2OEt2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-pentafluorophenyl esters, and, in these cases, is conducted using untreated, reagent grade CH2C12 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds. Thieme Stuttgart.