72036-31-8

Basic information

• Product Name: 2-Pentynoic acid, 4-hydroxy-4-phenyl-, ethyl ester
• CAS NO: 72036-31-8
• Molecular Formula: C13H14O3
• Molecular Weight: 218.252
• Mol File: 72036-31-8.mol

Chemical Properties

• CAS DataBase Reference: 2-Pentynoic acid, 4-hydroxy-4-phenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentynoic acid, 4-hydroxy-4-phenyl-, ethyl ester(72036-31-8)
• EPA Substance Registry System: 2-Pentynoic acid, 4-hydroxy-4-phenyl-, ethyl ester(72036-31-8)

Safety Data

• Hazardous Substances Data: 72036-31-8(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 623-47-2 propynoic acid ethyl ester 

Downstream Products

• 1366543-17-0 ethyl 4-(((allyloxy)carbonyl)oxy)-4-phenylpent-2-ynoate 
• 866476-05-3 benzoic acid 3-ethoxycarbonyl-1-methyl-1-phenyl-prop-2-ynyl ester 
• 866476-03-1 4-acetoxy-4-phenyl-pent-2-ynoic acid ethyl ester 
• 114702-20-4 3-(4-Methoxy-phenyl)-5-methyl-5-phenyl-5H-furan-2-one 
• 114702-32-8 4-(4-Methoxy-phenyl)-5-methyl-5-phenyl-5H-furan-2-one 

Relevant articles and documents

Regioselective annulation of propargyl alcohols with ambident-enols: A Ca(II)-catalyzed trisubstituted benzochromene synthesis

Highly regioselective, 6-endo cyclization between propargyl alcohols and ambident enols such as naphthols, 4-hydroxy coumarin, cyclohexane-1,3-dione, 5,5-dimethylcyclohexane-1,3-dione is described using Ca(OTf)2 under solvent free conditions. The reaction proceeds through a cascade annulation which involves an etherification, Claisen type rearrangement, allene formation and endocyclization. Further, we extended this method to the synthesis of iodo-derivative and demonstrated the reactivity in cross-coupling reactions.

Regiodivergent synthesis of functionalized indene derivatives via Pt-catalyzed Rautenstrauch reaction of propargyl carbonates

A regiodivergent synthesis of functionalized indene derivatives from a Pt-catalyzed Rautenstrauch reaction of propargyl carbonate is described. A one-pot Rautenstrauch/Tsuji-Trost reaction delivering 2-indanones was realized efficiently using this methodo

Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters

A highly selective and efficient Pt-catalyzed pentannulation reaction beginning from propargylic esters is described. The key to this reaction is the use of a PtCl2(PPh3)2/PhIO catalyst combination that allows the in situ

Study of the reaction of specifically substituted 2H-1,4 oxazin-2-ones with acetylenic compounds as a potential route for specific 3- or 4-pyridinecarboxylates

Cycloaddition-elimination reactions between 3,5-dichloro-2H-1,4-oxazin-2-one and ethyl 4-hydroxyalkynoates have been studied. 4,6-Dichlorofuropyridine-3(1H)ones have been generated, dechlorinated or transformed into the corresponding 3-pyridinecarboxylates.As the regioisomeric lactones and the corresponding 4-pyridinecarboxylates cannot be realised in this way, the synthesis of a 3-tributylstannyloxazinone and the regiochemistry of the cycloaddition with methyl propiolate has been studied.This route is shown to be inefficient for the generation of biologically interesting 4-pyridinecarboxylates.

THE PALLADIUM -TRIBUTYL FORMATE REAGENT IN THE STEREOSELECTIVE HYDROGENATION, AND STEREO- AND REGIOSELECTIVE HYDROARYLATION OF ALKYL 4-HYDROXY-2-ALKYNOATES: A ROUTE TO SUBSTITUTED BUTENOLIDES

The reaction of aryl iodides with alkyl 4-hydroxy-2-alkynoates in the presence of formic acid, tri-n-butylamine and a palladium(II) catalyst provides a convenient route to functionalized substituted butenolides through a one pot hydroarylation/cyclization reaction.In the presence of formic acid, tri-n-butylamine and a palladium(II) catalyst, alkyl 4-hydroxy-2-alkynoates undergo a one pot hydrogenation/cyclization reaction to the butenolide ring.By increasing the excess of formic acid, direct formation of saturated γ-lactones can be observed.Reaction occur with high stereoselectivity and, in the case of the hydroarylation, with goog regioselectivity.

Synthesis of Alkyl 4-Hydroxy-2-alkynoates

The lithium acetylide anion of ethyl or methyl propiolate is readily prepared by the addition of n-butyllithium to ethyl or methyl propiolate at low temperature.The anion rapidly adds to a variety of aldehydes or ketones to give ethyl or methyl 4-hydroxy-2-alkynoates in high yield.