4041-09-2

Usage

Uses

Used in Flavor and Fragrance Industry:
2,5-dimethylcyclopentan-1-one is used as a flavoring agent in food products for its fruity, sweet odor, enhancing the taste and aroma of various culinary creations.
2,5-dimethylcyclopentan-1-one is also used as a fragrance in perfumes, contributing to the development of unique and pleasant scents for personal care and cosmetic products.
Used in Pharmaceutical Industry:
2,5-dimethylcyclopentan-1-one serves as an intermediate in the production of pharmaceuticals, playing a crucial role in the synthesis of various medicinal compounds.
Used in Chemical Industry:
2,5-dimethylcyclopentan-1-one has industrial applications as an intermediate in the production of other chemicals, highlighting its versatility and importance in chemical synthesis processes.

InChI:InChI=1/C7H12O/c1-5-3-4-6(2)7(5)8/h5-6H,3-4H2,1-2H3

Upstream product

• 4748-92-9 meso-2,5-dimethyl-adipic acid 
• 19550-58-4 dimethyl 2,5-dimethylhexanedioate 
• 848761-77-3 3-cyano-1,3-dimethyl-2-oxo-cyclopentanecarboxylic acid ethyl ester 
• 4454-18-6 2,5-dimethyladipic acid 
• 108-24-7 acetic anhydride 
• 1120-72-5 2-Methylcyclopentanone 
• 74-88-4 methyl iodide 
• 4723-10-8 2,5-dimethyl-hexa-1,5-diene-3,4-diol 
• 55285-79-5 1,3-dimethyl-2-oxo-cyclopentanecarboxylic acid ethyl ester 
• 19935-89-8 N,N'-dinitroso-N,N'-butanediyl-bis-carbamic acid diethyl ester 
• 67-64-1 acetone 
• 4041-11-6 rac-2,5-dimethyl-2-cyclopenten-1-one 
• 84613-06-9 2,5-dimethyl-2-(p-tolylthio)cyclopentanone 
• 50-00-0 formaldehyd 

Downstream Products

• 4041-11-6 rac-2,5-dimethyl-2-cyclopenten-1-one 
• 62184-82-1 1,3-dimethylcyclopent-1-ene 
• 138580-53-7 1S*,2R*,5S*-2,5-dimethyl-1-(3'-methyl-5'-phenylisoxazol-4'-yl)cyclopentan-1-ol 
• 26584-90-7 7-Methoxy-3'-methyl-1,2-cyclopentano-phenanthren 
• 2453-00-1 1,3-dimethylcyclopentane 
• 125029-51-8 2,5-Dimethyl-cyclopentanone O-(4-bromo-3-methyl-phenyl)-oxime 
• 84613-06-9 2,5-dimethyl-2-(p-tolylthio)cyclopentanone 

Relevant academic research and scientific papers

METHOD FOR INTRODUCING SUBSTITUENT INTO alpha,beta-UNSATURATED KETONE AND METHOD FOR SYNTHESIZING PROSTAGLANDIN USING THE SAME

The present invention provides a method for introducing substituents into the α-position and the β-position of an α,β-unsaturated ketone, which not only can be used for the synthesis of a prostaglandin by a three-component coupling process, but also enables synthesis of a prostaglandin in a high yield by one-pot operation without requiring the use of a large excess amount of any of the three components required for the synthesis or using a highly toxic heavy metal as a catalyst or a solvent that is highly toxic to living bodies, and a method for synthesizing a prostaglandin using the same technical means. The method for introducing substituents into an α,β-unsaturated ketone according to the present invention is a method for introducing substituents into the carbon at the α-position and the carbon at the β-position of an α,β-unsaturated ketone, including: a first step of mixing alkyllithium and trialkylalkenyl tin in which tin atom binds to the vinyl position of the alkenyl group; a second step of mixing the mixture of the first step and dialkylzinc; a third step of mixing the mixture of the second step and an α,β-unsaturated ketone; and a fourth step of mixing the mixture of the third step and a trifluoromethanesulfonate compound.

Organozinc-aided, HMPA-free, stoichiometric three-component coupling for the general synthesis of prostaglandins and stable prostacyclin analogs with biological significance

A three-component coupling procedure was developed to construct the entire prostaglandin (PG) skeleton under HMPA-free and stoichiometric conditions via a combination of dimethylzinc-aided conjugate addition of an ω-side-chain vinyllithium with (R)-4-hydroxy-2-cyclopentenone and the direct trapping of the resulting enolate with an α-side-chain propargyl triflate. Dimethylzinc effectively regulated both the conjugate addition and alkynylation reactions. Thus, the method afforded protected 5,6-didehydro-PGE2, a common intermediate for the general synthesis of natural PGs and the stable artificial prostacyclin (PGI2) analog isocarbacyclin in 88% yield. The utility of the method was further applied to the syntheses of novel intermediates, which are useful for the straightforward synthesis of 15R-TIC and 15-deoxy-TIC in 79% and 86% yield, respectively.

ORGANIC COMPOUND USED AS FRAGRANCE INGREDIENTS

A compound of formula I wherein R1, R2, R3 and R4 can be independently selected from H or Me, n ＝ 0, 1, the dotted lines are indicating single bonds, or in case n ＝ 0 an isolated double bond at position 3', or in case n ＝ 1 an isolated double bond at position 3' or 4', and the wavy bond is indicating an unspecified configuration of the adjacent double bond. Said compounds, as well as precursors capable to generate said compounds, are useful as fragrance ingredients.

Regioselective synthesis of 2,2-dimethylcyclopentanone using 2-pyrrolidone magnesium salt as electrogenerated base

An efficient, direct and regioselective preparation of 2,2-dimethylcyclopentanone, via its enolate precursor regioselectively obtained using the 2-pyrrolidone magnesium salt, a base electrogenerated in DME/HMPA, is reported.

Highly regioselective alkylation at the more hindered α-site of unsymmetrical ketones by use of their potassium enolates. A comparative study with lithium enolates

Alkylation of regioisomeric potassium enolates 4 and 6 obtained from corresponding silyl enol ethers 2 and 3 occurs at the most substituted site affording ketones 8. Alkylation of corresponding lithium enolates 5 and 7 occurs at the expected site affording ketones 8 or 9. As an application the one pot synthesis of spiroketones 13 from silyl enol ethers 12 is described.

Preparation of aliphatic carboxylic acids by oxidation of monocyclic ketones

Aliphatic carboxylic acids, e.g., adipic acid, are prepared by oxidizing a monocyclic ketone with molecular oxygen or an oxygen-containing gas, in the presence of a catalytically effective amount of a vanadium compound having one of following formulae (I) and (II): in which n is an integer greater than or equal to 1 and less than or equal to 6; M is a molybdenum or tungsten atom; y is an integer ranging from zero to less than 50; Y is an acetylacetonate group or an alkoxy radical containing from 1 to 10 atoms; and m is 2 or 3.

Inducibility of an Enone Reductase System in the Fungus Beauveria sulfurescens: Application in Enantioselective Organic Synthesis

Microbiological reduction of α,β-unsaturated carbonyl compounds is studied.Inducibility of the enone reductase system of Beauveria sulfurescens is reported.The best inducer is shown to be cyclohex-2-en-1-one.An appropriate procedure using induced resting mycelium is developed to reduce substituted cyclohexenones that are shown to be unable to induce the reducing enzyme.Optically pure trans-(2R,6R)-(-)-2,6-dimethylcyclohexan-1-one and trans-(2R,6R)-(-)-2,6-dimethylcyclohexan-1-ol are obtained from (+/-)-2,6-dimethylcyclohex-2-en-1-one along with optically pure (6S)-(-)-2,6-dimethylcyclohex-2-en-1-one.

A NEW SYNTHESIS OF CYCLOPENTANONES BY THE RING EXPANSION OF 1-ACYL-1-CYCLOBUTANES

A new ring expansion of 1-acyl-1-cyclobutanes to give 2-cyclopentanones and its application to the synthesis of 2-, 2,4-, or 2,5-substituted cyclopentanones were studied.

The Synthesis of 2,5-Dialkylcyclopentanones from Aliphatic Aldehydes and Formaldehyde

Aliphatic aldehydes react with formaldehyde in the presence of dimethylamine hydrochloride at 200 deg C to form 2,5-dialkylcyclopentanones in moderate yields.Propanal, butanal, and pentanal give 2,5-dimethyl-, 2,5-diethyl-, and 2,5-dipropylcyclopentanone respectively, but ethanal gives only a tarry material.