26828-48-8

Usage

Uses

Used in Polymer Synthesis:
2-ALLYL-2-METHYL-1,3-CYCLOPENTANEDIONE is used as a monomer in the production of copolymers containing pendant substituted 5-membered rings as side groups. The compound undergoes copolymerization with ethylene, which allows for the creation of polymers with specific properties tailored for various applications.
Used in Chemical Industry:
In the chemical industry, 2-ALLYL-2-METHYL-1,3-CYCLOPENTANEDIONE can be utilized as an intermediate in the synthesis of various chemicals and materials. Its reactivity and structural features make it a valuable component in the development of new compounds with potential applications in different sectors.
Used in Research and Development:
Due to its unique structure and properties, 2-ALLYL-2-METHYL-1,3-CYCLOPENTANEDIONE is also used in research and development for exploring new chemical reactions and understanding its potential in creating novel materials and compounds. This can lead to the discovery of new applications and industries where 2-ALLYL-2-METHYL-1,3-CYCLOPENTANEDIONE can be effectively utilized.

Synthesis Reference(s)

Synthesis, p. 845, 1986 DOI: 10.1055/s-1986-31800

InChI:InChI=1/C9H12O2/c1-3-6-9(2)7(10)4-5-8(9)11/h3H,1,4-6H2,2H3

Upstream product

• 765-69-5 2-Methylcyclopentane-1,3-dione 
• 106-95-6 allyl bromide 
• 108264-62-6 3-Allyl-3-methyl-2,4-dioxo-cyclopentanecarboxylic acid ethyl ester 
• 107-05-1 3-chloroprop-1-ene 
• 35466-83-2 allyl methyl carbonate 
• 1469-70-1 allyl ethyl carbonate 
• 108264-57-9 Diethyl 2-allyl-2-methyl-3-oxohexanedioate 
• 107-18-6 allyl alcohol 
• 591-87-7 Allyl acetate 

Downstream Products

• 109121-09-7 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 109121-07-5 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 109064-53-1 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 109121-08-6 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-2-allyl-2-methyl-3-oxo-cyclopentyl ester 
• 72345-34-7 (+)-(2S,3S)-3-Hydroxy-2-methyl-2-(prop-2-enyl)-cyclopentanon 
• 81969-80-4 (2S,3R)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one 
• 109120-84-5 (2S,3S)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one 
• 109120-85-6 (2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one 
• 129303-10-2 (3R,4aR,7aS)-7a-Hydroxy-4a-methyl-3-phenylsulfanylmethyl-hexahydro-cyclopenta[c][1,2]dioxin-5-one 
• 690660-57-2 2-Methyl-2-((E)-4-oxo-pent-2-enyl)-cyclopentane-1,3-dione 
• 690660-55-0 2-methyl-2-[(2E)-4-oxo-4-phenylbut-2-en-1-yl]cyclopentane-1,3-dione 
• 42050-72-6 cis-(+/-)-2-allyl-3-hydroxy-2-methylcyclopentanone 
• 518322-39-9 2-methyl-2-(4-oxo-4-phenylbut-2-enyl)cyclopentane-1,3-dione 
• 1287695-71-9 (1S,2R,3R)-2-allyl-3-(tert-butyldimethylsiloxy)-1-(5-(4-(tert-butyldiphenylsiloxy)-butyl)furan-2-yl)-2-methylcyclopentanol 

Relevant academic research and scientific papers

A Total Synthesis of (-)-Hamigeran B and (-)-4-Bromohamigeran B

A concise synthesis of (-)-hamigeran B and (-)-4-bromohamigeran B is presented. The key reactions include a Suzuki coupling of enol triflate 15 with arylboronic ester for efficient synthesis of the densely 1,2,3-trisubstituted cyclopentene 23, a coordinat

Synthesis of quaternary-carbon-containing and functionalized enantiopure pentanecarboxylic acids from biocatalytic desymmetrization of meso-cyclopentane-1,3-dicarboxamides

Catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase-amidase containing microbial whole-cell catalyst under mild conditions, enantioselective desymmetrizations of meso-cyclopentane-1,3-dicarbonitriles and cyclopentane-1,3-dicarboxamides were studied. Although the nitrile hydratase was found to exhibit high enzymatic activity, but low 1R enantioselectivity toward dinitriles, a number of 2,2-unsymmetrically substituted meso-cyclopentane-1,3-dicarboxamide substrates were converted by the 1S enantioselective amidase into quaternary carbon-bearing enantiopure (1S,2R,3R)-3-carbamoylcyclopentanecarboxylic acids in yields up to 94%. The application of the method was demonstrated by convenient and practical transformations of the resulting (1S,2R,3R)-2-allyl-3-carbamoylcyclopentanecarboxylic acid derivatives into functionalized cyclopentane-fused δ-lactam and δ-lactone compounds.

Synthetic Studies on Enantioselective Total Synthesis of Cyathane Diterpenoids: Cyrneines A and B, Glaucopine C, and (+)-Allocyathin B2

The details for the synthetic studies on enantioselective total synthesis of cyathane diterpenoids cyrneine A (1) and B (2), glaucopine C (3), and (+)-allocyathin B2 are presented. We established a mild Suzuki coupling for heavily substituted n

First Enantioselective Catalytic Wittig Reaction

Herein we present the first catalytic enantioselective Wittig reaction. Chiral mono- and diphosphines were employed as catalysts for the desymmetrization of a prochiral ketone. The reaction was performed under microwave dielectric heating as well as under conventional heating. Selected catalysts led to moderate to good yields and enantioselectivities. In the presence of (+)-1,2-bis[(2S,5S)-2,5-dimethylphospholano]benzene [(S,S)-Me-DuPhos], an enantiomeric excess of up to 90 % was obtained.

Desymmetric enantioselective reduction of cyclic 1,3-diketones catalyzed by a recyclable p-chiral phosphinamide organocatalyst

The P-stereogenic phosphinamides are a structurally novel skeletal class which has not been investigated as chiral organocatalysts. However, chiral cyclic 3-hydroxy ketones are widely used as building blocks in the synthesis of natural products and bioactive compounds. However, general and practical methods for the synthesis of such chiral compounds remain underdeveloped. Herein, we demonstrate that the P-stereogenic phosphinamides are powerful organocatalysts for the desymmetric enantioselective reduction of cyclic 1,3-diketones, providing a useful method for the synthesis of chiral cyclic 3-hydroxy ketones. The protocol displays a broad substrate scope that is amenable to a series of cyclic 2,2-disubstituted five- and six-membered 1,3-diketones. The chiral cyclic 3-hydroxy ketone products bearing an all-carbon chiral quaternary center could be obtained with high enantioselectivities (up to 98% ee) and diastereoselectivities (up to 99:1 dr). Most importantly, the reactions could be practically performed on the gram scale and the catalysts could be reused without compromising the catalytic efficiency. Mechanistic studies revealed that an intermediate formed from P-stereogenic phosphinamide and catecholborane is the real catalytically active species. The results disclosed herein bode well for designing and developing other reactions using P-stereogenic phosphinamides as new organocatalysts.

Convenient preparation of synthetically useful chiral quaternary carbon-containing bicyclic compounds with organocatalysts

Chiral quaternary carbon-containing bicyclic compounds possessing carbonyl functionalities were efficiently synthesized through asymmetric intramolecular aldol reactions with organocatalysts. Bicyclo [3.3.0] and [3.4.0] systems were constructed with a dia

Chiral Phosphoric Acid Catalyzed Desymmetrization of Cyclopentendiones via Friedel–Crafts Conjugate Addition of Indolizines

An organocatalytic highly diastero- and enantioselective Friedel–Crafts conjugate addition of indolizines to prochiral cyclopentenediones has been successfully developed. This desymmetric transformation provides a direct access to the desired indolizine-substituted cyclopentanediones in yields of 62–91% and excellent stereoselectivities. The utility of the approach was demonstrated by diverse late-stage functionalizations through reduction or oxidation. Importantly, the direct sp2 C–H functionalization with nitromethane in one-pot process resulted in the indolizine-linked axially chiral styrene bearing a remote chiral center.

Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts

We have developed biocatalytic methods for the stereoselective reduction of cyclic prochiral 1,3-diketones for the production of optically active β-hydroxyketones and/or 1,3-diols. The recombinant ketoreductase KRED1-Pglu (formulated as purified catalyst)

Enantio- and Diastereoselective Synthesis of Functionalized Carbocycles by Cu-Catalyzed Borylative Cyclization of Alkynes with Ketones

A single-pot Cu-catalyzed enantio- and diastereoselective tandem hydroboration/borylative cyclization of alkynes with ketones for the synthesis of carbocycles is reported. The reaction proceeds via desymmetrization and generates four contiguous stereocent

Regio- and Stereoselective Syntheses of 7-Oxabicyclo[2.2.1]heptanes via a Gold(I)-Catalyzed Cycloisomerization of Alkynediols: Asymmetric Total Synthesis of Farnesiferol C

A highly regio- and stereoselective method to construct a broad range of 7-oxabicyclo[2.2.1]heptanes, which proceeds through a sequential reaction involving gold(I)-catalyzed cycloisomerization of alkynediols and sequential semi-pinacol-type 1,2-alkyl migration, was developed. The developed chemistry was applied to the asymmetric total synthesis of the natural product farnesiferol C.