100518-52-3

Usage

Physical state

Colorless to light yellow liquid

Molecular weight

160.21 g/mol

Functional groups

Alkyne and alcohol

Member of

Alkynyl alcohols

Usage

Organic synthesis, building block for other compounds, potential use in pharmaceutical and agrochemical industries

Safety concerns

Flammable, may cause skin and eye irritation

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 78-85-3 2-methylpropenal 
• 536-74-3 phenylacetylene 
• 4440-01-1 lithium phenylacetylide 

Downstream Products

• 1133296-12-4 C₁₅H₂₀OSi 
• 1385018-16-5 (E)-(3-methyl-5-oxocyclopent-2-en-1-ylidene)(phenyl)methyl acetate 
• 1385018-34-7 (Z)-(3-methyl-5-oxocyclopent-2-en-1-ylidene)(phenyl)methyl acetate 
• 1385017-97-9 2-methyl-5-phenylpent-1-en-4-yn-3-yl acetate 
• 65193-35-3 3-methyl-6-phenyl-2,3-dihydro-pyran-4-one 
• 73901-89-0 4-methyl-1-phenyl-4-penten-1-yn-3-one 
• 114303-24-1 1-diethylamino-4-methyl-1-phenyl-penta-1,4-dien-3-one 
• 62763-41-1 2-methyl-5-phenyl-1-pentene-3,5-dione 
• 2397-82-2 5-methyl-2-phenyl-pyran-4-one 

Relevant academic research and scientific papers

Rhodium-catalysed arylative annulation of 1,4-enynes with arylboronic acids

The rhodium(I)-catalysed arylative annulation of 1,4-enynes with arylboronic acids was investigated. The reaction was found to proceed via an addition-1,4-rhodium migration-addition sequence, affording the corresponding 1,1-disubstituted 3-(arylmethylene)indanes.

Double gold-catalysed annulation of indoles by enynones

The gold-catalysed double functionalisation of indoles is presented. Enynones are used to annulate indoles via a double sodium tetrachloroaurate- catalysed process involving a mixture of C-H activation and alkyne activation modes of promotion. Good yields

Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)2]2

A class of alkenyl propargyl acetates, RCH(OAc)C≡CC(CH 3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)2]2 in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents, up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.

Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution

Gold-catalyzed reactions of 3-silyloxy-1,4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-me