934-42-9

Usage

Uses

Used in Flavor and Fragrance Industry:
2-butylcyclopentanone is used as a flavoring agent for its fruity aroma, enhancing the taste and smell of food products. It is also utilized as a fragrance in perfumes and personal care products, adding a pleasant scent to these consumer goods.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-butylcyclopentanone serves as a key intermediate in the synthesis of various organic compounds, contributing to the development and production of different medicinal drugs.
Used in Chemical Synthesis:
2-butylcyclopentanone is employed as a versatile building block in the synthesis of other organic compounds, playing a crucial role in the chemical industry for creating a wide range of products.

InChI:InChI=1/C9H16O/c1-2-3-5-8-6-4-7-9(8)10/h8H,2-7H2,1H3

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 120-92-3 cyclopentanone 
• 16424-32-1 2-Buthylidenecyclopentenone 
• 631-61-8 ammonium acetate 
• 1003-03-8 Cyclopentamine 
• 542-69-8 1-iodo-butane 
• 1192-28-5 Cyclopentanone oxime 
• 42908-34-9 N-cyclohexyl-N-cyclopentylidenamine 
• 72653-67-9 2-(1-phenylthiobutyl)cyclopentanone 
• 62803-93-4 2-(1-Butenyl)-2-cyclopentenon 
• 56292-42-3 (E)-2-butylidene-1-cyclopentanone 
• 109-65-9 1-bromo-butane 
• 14090-60-9 2-cyclopentylidene-1,1-dimethylhydrazine 
• 5561-05-7 2-butylcyclopent-2-enone 

Downstream Products

• 3301-94-8 6-Butyl-tetrahydro-pyran-2-one 
• 1239335-22-8 (1R,2S)-4-methoxy-N-(2-butylcyclopentyl)aniline 
• 1497405-24-9 C₂₂H₂₇NO 
• 1497405-14-7 (3aS,8bS)-4-benzyl-8b-butyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole 
• 1337968-21-4 C₁₁H₂₀O₂ 
• 2801-82-3 cis-1,2-dibutylcyclopentane 
• 2801-82-3 trans-1,2-dibutylcyclopentane 
• 102707-15-3 N-(2-butyl-cyclopentyl)-N-cyclopentyl-N'-phenyl-urea 

Relevant academic research and scientific papers

Strictly regiocontrolled α-monosubstitution of cyclic carbonyl compounds with alkynyl and alkyl groups via Pd-catalyzed coupling of cyclic α-iodoenones with organozincs

The conditions for the Pd-catalyzed cross coupling of cyclic α-iodoenones, such as 2-iodo-2-cyclohexenone, with alkynylzincs have been optimized. The use of tris(o-furyl)phosphine (TFP) as a ligand and DMF as a solvent has led to the formation of α-alkynylenones in excellent yields. This optimized procedure has been applied to the synthesis of (±)-harveynone and (±)-tricholomenyn A in high yields. Investigation of related α-alkylation reactions using alkylzincs has revealed the following. Methylzinc and primary alkylzinc derivatives readily undergo Pd-catalyzed cross coupling with α-iodoenones. Although (s-Bu)2Zn also undergoes Pd-catalyzed cross coupling, only the n-Bu-substituted products were obtained, α-Benzylation and α-homobenzylation can proceed satisfactorily, whereas allylzinc and propargylzinc derivatives undergo only addition to the carbonyl group. Although some promising results have been obtained in α-homoallylation and α-homopropargylation, these reactions need to be further improved. (C) 2000 Elsevier Science Ltd.

Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones

Optically active α-methyl α-substituted cycloalkanones are prepared by a chemoenzymatic sequence which involves a Lipozyme-catalyzed transesterification of 1-(chloroacetoxy)bicyclo[n.1.0]alkanes and ring opening of these cyclopropanol derivatives.

Consecutive 6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions

A range of substituted Se-phenyl 5,9-dieneselenoates, viz. 15a, 25, 26, 27, 42 and 52, have been synthesised and their reactions with Bu3SnH-AIBN investigated.The diene esters 15a, 42 and 52 are shown to lead to decalone and to perhydrophenanthrone derivatives, viz. 19, 43 and 53, respectively, via consecutive 6-endo trig modes of cyclisations starting from the corresponding 5,9-diene acyl radical intermediates.By contrast, the 5,9-dienoates 25 and 27 lacking alkyl substitution at C-9 instead underwent cyclisation to the indanones 36 and 37, respectively, and the 6-methyl substituted analogue 26 produced only the cyclopentanone 38 on treatment with Bu3SnH-AIBN.

The alkylation of silyl enol ethers with SN1-unreactive iodides in the presence of silver trifluoroacetate

Silyl enol ethers can be effectively alkylated with primary n-alkyl iodides in the presence of silver trifluoro-acetate to give monoalkyl ketones.

An Organozinc Aid in Alkylation and Acylation of Lithium Enolates

The presence of dimethylzinc in the reaction of lithium enolates and electrophiles effectively suppresses undesired α-proton exchange reaction and enhances the efficiency of enolate alkylation and acylation.

α-ALKYLATION AND α-ALKYLIDENATION OF CARBONYL COMPOUNDS BY O-SILYLATED ENOLATE PHENYLTHIOALKYLATION

For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates.In the case of α-alkylation of carbonyl compounds, Lewis acid (TiCl4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, Bui, and Me3Si), followed by reductive sulphur removal by Raney nickel, 5->6, is found to be a reliable method for this synthetically important C-C bond forming step.An alternative sulphur elimination pathway via the sulphoxide, 5->7, allows the regio- and stereocontrolled α-alkylidenation of carbonyl compounds.The phenylthioalkylation reaction is applicable to ketones, aldehydes, esters, and lactones.

Amphiphilic Reactions by Means of Exceptionally Bulky Organoaluminum Reagents. Rational Approach for Obtaining Unusual Equatorial, Anti-Cram, and 1,4 Selectivity in Carbonyl Alkylation

Exceptionally bulky, oxygenophilic organoaluminum reagents, methylaluminum bis(2,6-di-tert-4-alkylphenoxide) (MAD and MAT), have been successfully utilized for stereoselective activation of carbonyl moiety.Combination of MAD or MAT with carbon nucleophiles such as organolithiums or Grignard reagents generates a new amphiphilic reaction system in which the alkylation may be interpreted as the nucleophilic addition of a reactive organometallic compound to an electrophilically activated carbonyl substrate in order to account for the regio- and stereochemical consequences.In contrast to the ordinary alkylations, the amphilic alkylation disclosed herein would be categorized into the new, yet unexplored class of alkylation that exhibits high chemoselectivity to carbonyl compounds, and more significantly it allows excellent equatorial and anti-Cram selectivity in carbonyl alkylations, hitherto difficult by the existing methodologies.Further, unusual conjugate addition of organolithium reagents to α,β-unsaturated carbonyl compounds has been accomplished by using the amphiphilic reaction system.

Prostaglandin analogue

A novel prostaglandin analogue of the formula: STR1 [wherein the symbol represents β-configuration, the dotted line ---------- represents α-configuration, and the double bond between C13 -C14 represents transconfiguration] and cyclodextrin clathrates thereof, and non-toxic salts thereof are useful for the treatment and/or prevention of diseases induced by platelet aggregation, such as thrombosis, or induced by cytodamage.

Five-membered ring spiro-annulation via thermal rearrangement of enol silyl ethers of 2-(cyclopropylmethylene)cycloalkanones. A formal total synthesis of some spirovetivane-type sesquiterpenoids

Treatment of the 2-(iodomethylene)cycloalkanones 10 and 11 with lithium (phenylthio)(cyclopropyl)cuprate provided good yields of the corresponding β-cyclopropyl enones 12 and 13, respectively.Thermolysis of the latter substances produced relatively poor yields of the desired spiro-annulation products 14 and 15.However, conversion of 12 and 13 into the corresponding enol silyl ethers 24 and 25, followed by thermal rearrangement of the latter materials and acid hydrolysis of the resulting products, provided synthetically useful yields of the spiro enones 14 and 15.Cuprous iodide-catalyzed addition of methyl magnesium iodide to 2-cyclohexen-1-one, followed by trapping of the resultant enolate anion with cyclopropanecarboxaldehyde, provided the ketols 38, which could be converted into the mixture of enol silyl ethers 34 and 35.Thermal rearrangement of the latter substances gave, after acid hydrolysis of the crude thermolysate, the spiro enones 42 and 43 in a ratio of ca. 2.5 : 1 (57 percent yield).Treatment of 42 with methyllithium in ether gave the tertiary alcohols 44 and 45 (ratio ca. 4 : 1).Hydroboration (disiamylborane, tetrahydrofuran; H2O2, NaOH) of 44, followed by oxidation of the resultant diol 46 with pyridinium chlorochromate, provided the ketol 47.A similar sequence of reactions converted the olefinic alcohol 45 into the ketol 49.Dehydration (p-toluenesulfonic acid in benzene) of 47 gave the spiro enones 28 and 48, in a ratio of ca. 9 : 1.Compound 28, also prepared previously from the ketol 49, had been converted earlier into the spirovetivane-type sesquiterpenoids (+/-)-α-vetispirene (29), (+/-)-vetivone (30), (+/-)-hinesol (31), (+/-)-hinesol acetate (32), and (+/-)-agarospirol (33).