6672-30-6

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-3-METHYLCYCLOPENTANONE is used as a building block for the production of pharmaceuticals, contributing to the development of new drugs and medications due to its unique chemical properties.
Used in Flavor and Fragrance Industry:
(R)-(+)-3-METHYLCYCLOPENTANONE is used as a key component in the synthesis of flavoring agents and perfumes, enhancing the sensory experience of various products by imparting specific scents and tastes.
Used in Industrial Processes:
(R)-(+)-3-METHYLCYCLOPENTANONE is utilized as a solvent in some industrial processes, facilitating chemical reactions and contributing to the efficiency of manufacturing operations.
Used in Food Industry:
(R)-(+)-3-METHYLCYCLOPENTANONE has potential applications in the food industry, where it may be used in the development of new flavor profiles and the enhancement of existing food products.

InChI:InChI=1S/C6H10O/c1-5-2-3-6(7)4-5/h5H,2-4H2,1H3/t5-/m0/s1

Upstream product

• 623-82-5 (R)-3-methylhexanedioic acid 
• 917-64-6 methyl magnesium iodide 
• 79681-26-8 2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one 
• 930-30-3 cyclopent-2-enone 
• 917-54-4 methyllithium 
• 3973-43-1 4-methylpent-4-enal 
• 110967-37-8 (S)-(-)-4-methyl-2-cyclopentenone 
• 118621-18-4 (2R,4R)-2-Methoxy-4-methyl-cyclopentanone 
• 2758-18-1 3-Methyl-2-cyclopenten-1-one 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 591-24-2 3-Methylcyclohexanone 
• 544-97-8 dimethyl zinc(II) 
• 890524-49-9 diisopropyl 3R-methylhexane-1,6-dioate 

Downstream Products

• 18729-48-1 3-methylcyclopentanol 
• 87921-02-6 2,5-dibenzylidene-3-methyl-cyclopentanone 
• 114218-64-3 (R)-1-methyl-cyclopentan-3-one-phenylhydrazone 
• 930-59-6 (1R,3R)-3-methylcyclopentanol 
• 3728-67-4 1-Methyl-3-propyl-cyclopentan 
• 5078-75-1 1-Phenyl-3-methylcyclopentylbenzen 
• 152518-80-4 (1R,2R)-1-phenyl-2-methylcyclopentane 
• 152518-79-1 (1R,2R)-1-phenyl-2-methylcyclopentane 
• 1120-62-3 3-methyl-1-cyclopentene 
• 342652-10-2 (Z)-cyano-((R)-3-methyl-cyclopentylidene)-acetic acid ethyl ester 
• 342652-12-4 (E)-cyano-((R)-3-methyl-cyclopentylidene)-acetic acid ethyl ester 
• 87921-02-6 (+)-2,5-dibenzylidene-3-methylcyclopentanone 
• 61898-56-4 (S)-4-methyltetrahydro-2H-pyran-2-one 
• 2857-75-2 (R)-4-methyl-δ-valerolactone 

Relevant academic research and scientific papers

Synthesis of optically pure 3R-methylcyclopentan-1-one from L-(-)-menthol

Synthesis of optically pure 3R-methylcyclopentan-1-one using in the key step Dieckmann cyclization of diisopropyl 3R-methylhexan-1,6-dioate, which is accessible from L-(-)-menthol, was proposed. 2005 Springer Science+Business Media, Inc.

A robust and stereocomplementary panel of ene-reductase variants for gram-scale asymmetric hydrogenation

We report an engineered panel of ene-reductases (ERs) from Thermus scotoductus SA-01 (TsER) that combines control over facial selectivity in the reduction of electron deficient C[dbnd]C double bonds with thermostability (up to 70 °C), organic solvent tolerance (up to 40 % v/v) and a broad substrate scope (23 compounds, three new to literature). Substrate acceptance and facial selectivity of 3-methylcyclohexenone was rationalized by crystallisation of TsER C25D/I67T and in silico docking. The TsER variant panel shows excellent enantiomeric excess (ee) and yields during bi-phasic preparative scale synthesis, with isolated yield of up to 93 % for 2R,5S-dihydrocarvone (3.6 g). Turnover frequencies (TOF) of approximately 40 000 h?1 were achieved, which are comparable to rates in hetero- and homogeneous metal catalysed hydrogenations. Preliminary batch reactions also demonstrated the reusability of the reaction system by consecutively removing the organic phase (n-pentane) for product removal and replacing with fresh substrate. Four consecutive batches yielded ca. 27 g L?1 R-levodione from a 45 mL aqueous reaction, containing less than 17 mg (10 μM) enzyme and the reaction only stopping because of acidification. The TsER variant panel provides a robust, highly active and stereocomplementary base for further exploitation as a tool in preparative organic synthesis.

Counterion Enhanced Organocatalysis: A Novel Approach for the Asymmetric Transfer Hydrogenation of Enones

We present a novel strategy for organocatalytic transfer hydrogenations relying on an ion-paired catalyst of natural l-amino acids as main source of chirality in combination with racemic, atropisomeric phosphoric acids as counteranion. The combination of a chiral cation with a structurally flexible anion resulted in a novel chiral framework for asymmetric transfer hydrogenations with enhanced selectivity through synergistic effects. The optimized catalytic system, in combination with a Hantzsch ester as hydrogen source for biomimetic transfer hydrogenation, enabled high enantioselectivity and excellent yields for a series of α,β-unsaturated cyclohexenones under mild conditions. Moreover, owing to the use of readily available and chiral pool-derived building blocks, it could be prepared in a straightforward and significantly cheaper way compared to the current state of the art.

Enantio- A nd regioselective: Ene-reductions using F420H2-dependent enzymes

In the past decade it has become clear that many microbes harbor enzymes that employ an unusual flavin cofactor, the F420 deazaflavin cofactor. Herein we show that F420-dependent reductases (FDRs) can successfully perform enantio-, regio- A nd chemoselective ene-reductions. For the first time, we have demonstrated that F420H2-driven reductases can be used as biocatalysts for the reduction of α,β-unsaturated ketones and aldehydes with good conversions (>99%) and excellent regioselectivities and enantiomeric excesses (>99% ee). Noteworthily, FDRs typically display an opposite enantioselectivity when compared to the well established FMN-dependent Old Yellow Enzymes (OYEs).

Imido-P(v) trianion supported enantiopure neutral tetrahedral Pd(II) cages

Charge-neutral chiral hosts are attractive due to their ability to recognize a wide range of guest functionalities and support enantioselective processes. However, reports on such charge-neutral cages are very scarce in the literature. Here, we report an enantiomeric pair of tetrahedral Pd(ii) cages built from chiral tris(imido)phosphate trianions and oxalate linkers, which exhibit enantioselective separation capabilities for epichlorohydrin, β-butyrolactone, and 3-methyl- and 3-ethyl cyclopentanone.

Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones followed by trapping with allyl iodide derivatives

Enantioselective copper-catalyzed 1,4-addition of dialkylzincs to enones proceeded in the presence of 0.1 mol% of Cu(OTf)2 and 0.25 mol% of an N,N,P-ligand containing a quinoline moiety to afford the corresponding conjugated adducts in 99%ee. The intermediate zinc enolates were trapped with substituted allyl iodides to give disubstituted ketones with high diastereoselectivity and enantioselectivity.

Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3·Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested.

Copper-catalyzed asymmetric 1,4-conjugate addition of dialkylzinc to enones

Asymmetric 1,4-conjugation addition of dialkylzinc (diethylzinc and dimethylzinc) to cyclic enones, chalcone and nitroalkenes was achieved by a 25 mol% (R)-6,6'-Br2-BINOL(1f), 25 mol% CuSPh and 100 mol% dicyclohexylmethylamin(Cy2NMe) catalyst system. The Cu(I) catalyst system enables the cyclic enone, chalcone and nitroalkene generality with high enantioselectivity (up to84%ee) and isolated yield (up to 94%) under mild reaction conditions.

Directed evolution of an enantioselective enoate-reductase: Testing the utility of iterative saturation mutagenesis

Directed evolution utilizing iterative saturation mutagenesis (ISM) has been applied to the old yellow enzyme homologue YqjM in the quest to broaden its substrate scope, while controlling the enantioselectivity in the bioreduction of a set of substituted cyclopentenone and cyclohexenone derivatives. Guided by the known crystal structure of YqjM, 20 residues were selected as sites for saturation mutagenesis, a pooling strategy based on the method of Phizicky [M. R. Martzen, S. M. McCraith, S. L. Spinelli, F. M. Torres, S. Fields, E. J. Grayhack, E. M. Phizicky, Science 1999, 286, 1153-1155] being used in the GC screening process. The genes of some of the hits were subsequently employed as templates for randomization experiments at the other putative hot spots. Both (R)-and (S)-selective variants were evolved using 3-methylcyclohexenone as the model substrate in the asymmetric bioreduction of the olefinic functionality, only small mutant libraries and thus minimal screening effort being necessary. Some of the best mutants also proved to be excellent catalysts when testing other prochiral substrates without resorting to additional mutagenesis/screening experiments. Thus, the results constitute an important step forward in generalizing the utility of ISM as an efficient method in laboratory evolution of enzymes as catalysts in organic chemistry.

Asymmetric catalysis: Resin-bound hydroxyprolylthreonine derivatives in enamine-mediated reactions

Control of stereochemistry is achieved using two TentaGel-bound di-tert-butoxyprotected hydroxyprolyl-threonine catalysts (see picture, sphere represents TentaGel). These catalysts mediate asymmetric tandem enamine/Michael reactions with high enantioselectivity and complete diastereoselectivity; the choice of catalyst depends on the desired absolute configuration. (Chemical Equation Presented).