117552-48-4

Basic information

• Product Name: 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2E)-
• CAS NO: 117552-48-4
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• Mol File: 117552-48-4.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2E)-(117552-48-4)
• EPA Substance Registry System: 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2E)-(117552-48-4)

Safety Data

• Hazardous Substances Data: 117552-48-4(Hazardous Substances Data)

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 116544-98-0 (Z)-2-iodo-3-phenylacrylaldehyde 
• 2579-22-8 Phenylpropargyl aldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 536-74-3 phenylacetylene 
• 5443-49-2 α-bromocinnamaldehyde 
• 66894-04-0 2,3-dibromo-3-phenyl propanal 
• 14371-10-9 (E)-3-phenylpropenal 
• 131073-06-8 triethyl phosphonoacetate 
• 6142-95-6 phenylpropargyl aldehyde diethyl acetal 
• 161890-26-2 (E)-ethyl hex-2-en-4-ynoate 
• 501-65-5 diphenyl acetylene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 

Downstream Products

• 121491-39-2 ethyl (E)-3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloylate 
• 64907-51-3 (E)-(5-chloropent-3-en-1-yn-1-yl)benzene 
• 351863-99-5 (E)-(S)-2-ethoxy-3-[4-(5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester 
• 27948-28-3 (E)-5-phenyl-pent-2-en-4-ynoic acid 

Relevant articles and documents

Palladium-catalyzed oxidative alkynylation of alkenes via C-C bond cleavage under oxygen atmosphere

(Matrix presented) Palladium-catalyzed oxidative alkynylation of alkenes using tert-propargylic alcohols as alkynylation reagents via C-C bond cleavage under an oxygen atmosphere affords the corresponding ene-yne compounds.

Synthesis of Ethyl (2E)-5-Phenylpent-2-en-4-ynoate

An efficient procedure has been developed for the synthesis of ethyl (2E)-5-phenylpent-2-en-4-ynoate by olefination-dehydrohalogenation of (2Z)-2-iodo-3-phenylprop-2-enal prepared by iodination of commercially available cinnamaldehyde.

Facile synthesis of α, β-unsaturated esters through a one-pot copper-catalyzed aerobic oxidation-Wittig reaction

An efficient one-pot synthesis of α, β-unsaturated esters through the aerobic oxidation – Wittig tandem reaction of alcohols and phosphorous ylide is developed. This new method operates under mild reaction conditions, and uses CuI/TEMPO (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) as co-catalyst and air (O2) as the oxidant. It tolerates a wide range of functionalized benzylic alcohol and aliphatic alcohols.

Lewis Base Activation of Silyl Acetals: Iridium-Catalyzed Reductive Horner-Wadsworth-Emmons Olefination

A Lewis base promoted deprotonative pronucleophile addition to silyl acetals has been developed and applied to the iridium-catalyzed reductive Horner-Wadsworth-Emmons (HWE) olefination of esters and the chemoselective reduction of the resulting enoates. Lewis base activation of silyl acetals generates putative pentacoordinate silicate acetals, which fragment into aldehydes, silanes, and alkoxides in situ. Subsequent deprotonative metalation of phosphonate esters followed by HWE with aldehydes furnishes enoates. This operationally convenient, mechanistically unique protocol converts the traditionally challenging aryl, alkenyl, and alkynyl esters to homologated enoates at room temperature within a single vessel.