3859-41-4

Usage

Uses

1. Used in Chemical Synthesis:
1,3-Cyclopentanedione is used as a chemical intermediate for the synthesis of chemical probes for selective labeling of sulfenic acid proteins. This application is significant in the field of biochemistry and molecular biology, as it aids in the study and understanding of protein functions and interactions.
2. Used in Pharmaceutical Industry:
1,3-Cyclopentanedione is used as a synthetic precursor for the development of enaminones, which have potential anticonvulsant activity. This application is particularly relevant in the pharmaceutical industry, as it contributes to the discovery and development of new drugs for the treatment of epilepsy and other seizure disorders.
3. Used in Organic Chemistry:
In the field of organic chemistry, 1,3-Cyclopentanedione is utilized as a building block for the synthesis of various organic compounds, taking advantage of its reactive ketone groups and cyclic structure. This application highlights its importance as a versatile and valuable compound in the synthesis of a wide range of molecules with diverse properties and applications.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 2095, 1980 DOI: 10.1021/ja00526a059

Purification Methods

Purify the dione by Soxhlet extraction with CHCl3. The CHCl3 is evaporated and the residue is recrystallised from EtOAc and/or sublimed at 120o/4mm. [IR: Boothe et al. J Am Chem Soc 75 1732 1953, DePuy & Zaweski J Am Chem Soc 81 4920 1959, Beilstein 7 IV 1981.]

InChI:InChI=1/C5H6O2/c6-4-1-2-5(7)3-4/h3,6H,1-2H2

Upstream product

• 14000-78-3 6-Ethyl 1-methyl 3-oxohexane-1,6-dioate 
• 930-60-9 maleic anhydride 
• 14734-21-5 2,5-dioxo-cyclopentanecarboxylic acid ethyl ester 
• 14734-23-7 2-Carbaethoxy-4-carbo-tert.-butoxy-cyclopentan-1.3-dion 
• 130249-17-1 2,3-epoxycyclopentanone 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 73825-35-1 3-(N-phenylamino)-2-cyclopentene-1-one 
• 109459-59-8 1,4-dioxaspiro[4.4]nonan-7-one 
• 91920-55-7 methyl 1-hydroxy-4-oxocyclopent-2-enecarboxylate 
• 120-92-3 cyclopentanone 
• 41498-13-9 4,5-diiodo-4-cyclopentene-1,3-dione 
• 930-30-3 cyclopent-2-enone 
• 695-56-7 1,4-dioxaspiro[4.4]non-6-ene 
• 41498-12-8 4,5-dibromo-4-cyclopentene-1,3-dione 

Downstream Products

• 4683-50-5 3-methoxycyclopent-2-enone 
• 22627-70-9 3-ethoxycyclopent-2-en-1-one 
• 53102-14-0 3-chlorocyclopent-2-en-1-one 
• 109704-13-4 4-oxo-2-phenyl-1,2,3,4,5,6-hexahydro-1-oxapentalene 
• 128535-48-8 N-(2,5-Dioxo-2,5,6,7-tetrahydro-cyclopenta[b]pyran-3-yl)-benzamide 
• 142605-79-6 2,2,9,9-tetraphenyloctahydro-3,4,7,8-tetraoxabenzindene-4a,6a-diol 
• 150111-61-8 3-Hydroxy-2-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one 
• 504-02-9 1,3-cylohexanedione 
• 102306-78-5 6,7-dihydrocyclopenta[d][1,3]dioxin-5(4H)-one 
• 114908-47-3 C₁₃H₁₄O₅ 
• 77902-69-3 C₁₁H₈N₃O₈^(1-) 
• 127053-23-0 2-Phenylthio-1,3-cyclopentanedione 
• 5857-27-2 2-benzyl-3-hydroxy-2-cyclopenten-1-one 
• 73039-22-2 3-(benzoyloxy)-2-cyclopenten-1-one 

Relevant academic research and scientific papers

KINETIC RESOLUTION OF 4-HYDROXY-2-CYCLOPENTENONE BY RHODIUM-CATALYZED ASYMMETRIC ISOMERIZATION

Cationic Rh-BINAP complexes catalyze isomerization of racemic 4-hydroxy-2-cyclopentenone to 1,3-cyclopentadione with 5:1 enantiomeric discrimination.

Bio-based synthesis of cyclopentane-1,3-diamine and its application in bifunctional monomers for poly-condensation

A novel and green route for the synthesis of cyclopentane-1,3-diamine (CPDA) from hemicellulosic feedstock is established in this work. Through many explorations and optimizations, the single successful multi-step synthesis was found to comprise: (1) the Piancatelli rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone (4-HCP), (2) a highly improved isomerization of4-HCPinto cyclopentane-1,3-dione (CPDO) using the Ru Shvo catalyst, (3) conversion ofCPDOinto cyclopentane-1,3-dioxime (CPDX), and (4) a mild oxime hydrogenation ofCPDXover Rh/C to afford the desiredCPDA. In addition, diastereomerically purecis- andtrans-isomers ofCPDAwere reacted with (A) bio-based lactones, and (B) 5-(hydroxymethyl)furfural (HMF) to synthesize novel bifunctional diol monomers with internal amide and imine groups, respectively. Monomer5, derived using γ-valerolactone (GVL), was successfully applied in the synthesis of polyurethanes.

Rapid and Multigram Synthesis of Vinylogous Esters under Continuous Flow: An Access to Transetherification and Reverse Reaction of Vinylogous Esters

An environmentally benign approach for the synthesis of vinylogous esters from 1,3-diketone and its reverse reaction under continuous-flow has been developed with alcohols in the presence of inexpensive Amberlyst-15 as a catalyst. This methodology is highly selective and general for a range of cyclic 1,3-dicarbonyl compounds which gives a library of linear alkylated and arylated vinylogous esters in good to excellent yield under solvent and metal free condition. Furthermore, the long-time experiment in a continuous-flow up to 40 h afforded 8.0 g of the vinylogous ester with turnover number (TON) = 28.6 and turnover frequency (TOF) = 0.715 h-1 using Amberlyst-15 as a catalyst. Furthermore, a continuous-flow sequential transetherification of vinylogous esters with various alcohols has been achieved in high yield. Reversibly, this vinylogous ester was deprotected or hydrolyzed into ketone using environmentally benign water as a solvent and Amberlyst-15 as a catalyst under continuous-flow process.

Direct amination of bio-alcohols using ammonia

A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.

PROCESS FOR PRODUCTION OF SUBSTITUTED CYCLOPENTANONE

A substituted cyclopentanone represented by the formula (2) can be produced by hydrogenating the double bond in a compound represented by the formula (1) in the presence of a transition metal catalyst by using a carboxylic acid or a specific concentration of a carboxylic acid ester as a solvent. This process can produce a substituted cyclopentanone which is useful as an jasmine-flavored fragrance, an intermediate in the production of the fragrance or the like, in a simple and inexpensive manner at a high cis-form ratio; (1) wherein R1 and R2 represent a substituent having 1 to 8 carbon atoms; and (2) wherein R3 and R4 represent a substituent having 1 to 8 carbon atoms, may be the same as R1 and R2, and may be the same as each other.

Method for preparing chiral diphosphines

The invention concerns a method for preparing a compound of formula (1) wherein: A represents naphthyl or phenyl optionally substituted; and Ar1, Ar2independently represent a saturated or aromatic carbocyclic group, optionally substituted.

Asymmetric hydrogenation method of a ketonic compound and derivative

The present invention relates to a process for the asymmetric hydrogenation of a ketonic compound and derivative. The invention relates to the use of optically active metal complexes as catalysts for the asymmetric hydrogenation of a ketonic compound and derivative. The process for the asymmetric hydrogenation of a ketonic compound and derivative is characterized in that the asymmetric hydrogenation of said compound is carried out in the presence of an effective amount of a metal complex comprising as ligand an optically active diphosphine corresponding to one of the following formulae: STR1

A regioselective synthesis of 4-methyl-1-pyrindan-5-one

The enamine 7 reacts with crotonic aldehyde in the presence of p-toluenesulphonic acid via the intermediate 8 to yield regioselectively the unknown title compound 9. In alkaline medium, 9 is also formed from 7 and acetylacetaldehyde dimethyl acetal as well as small amounts of 11 and 12; under acidic conditions, however, mixtures of the regioisomers 9/9a are obtained in poor yield. 9a can be separated by fractional crystallisation of the hydrochlorides. Corresponding to 7 the homologous enamine 13 and acetylacetaldehyde acetal by alkaline catalysis gives the 4-methyltetrahydroquinolinone 1, respectively. Improved experimental details for an efficient preparation of the starting compounds 3 and 4 are given.

Inhibitors of the advanced glycosylation of proteins and methods of use therefor

The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with a carbonyl moiety of an early glycosylation product of such target proteins resulting from their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.

Process for the production of 1,3-cyclopentanedione

A process for the production of 1,3-cyclopentanedione, which is a versatile intermediate product for numerous active ingredient syntheses. For this purpose, a malonic acid ester is reacted with a haloalkoxybutenoic acid ester, the resultant bis-(alkoxycarbonyl) alkoxypentenoic acid ester is cyclized to alkoxycarbonyl alkoxycyclopentenone, the ester function is saponified, and finally the intermediate is decarboxylated to the end product.