16424-32-1

Usage

InChI:InChI=1/C9H14O/c1-2-3-5-8-6-4-7-9(8)10/h5H,2-4,6-7H2,1H3

Upstream product

• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 123-72-8 butyraldehyde 
• 1056246-36-6 2-bromocyclopentanone 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 110-62-3 pentanal 
• 120-92-3 cyclopentanone 
• 72653-67-9 2-(1-phenylthiobutyl)cyclopentanone 

Downstream Products

• 934-42-9 2-butylcyclopentanone 
• 825-25-2 2-cyclopentylidenecyclopentan-1-one 
• 109645-33-2 8-propyl-1,2,3,5,6,7-hexahydro-dicyclopenta[b,e]pyridine 
• 24071-99-6 Ethyl 5-oxononanoate 
• 102707-15-3 N-(2-butyl-cyclopentyl)-N-cyclopentyl-N'-phenyl-urea 
• 1319726-95-8 (1R,3R,4R,5R)-methyl 1-(4-chlorophenyl)-6-oxo-4-propyl-2-azaspiro[4.4]nonane-3-carboxylate 

Relevant academic research and scientific papers

Identification and synthesis of new volatile molecules found in extracts obtained from distinct parts of cooked chicken

Several chicken parts (skin, fat, juice) were cooked in different ways (roasting, simmering) and investigated separately for their volatile composition. In-depth GC/MS analysis of the separate fractions revealed several unknown molecules. Mass spectra interpretation allowed us to identify nine molecules for the first time in chicken, including cyclic aldehydes, cyclic ketones, and new δ-lactones containing an unsaturated linear chain. Identification was confirmed by chemical synthesis followed by comparison of the mass spectra and linear retention indices. The natural occurrence of five of these molecules is reported here for the first time in a natural product.

A new lewis acid system palladium/TMSCl for Catalytic aldol condensation of aldehydes with ketones

Palladium on charcoal effectively catalyzed the aldol condensation reactions of different ketones with aldehydes in the presence of trimethylsilyl chloride (TMSCl). The following reactions were investigated: (1) aromatic aldehydes with cycloalkanones, (2) aromatic aldehydes with aromatic ketones, (3) cycloalkanones with aliphatic aldehydes, and (4) the self-condensation reactions of aliphatic aldehydes and cycloalkanones.

Thioalkylation of Enolates, IV. α-Alkylidenecyclopentanones by α-Alkylidation of Methyl 2-Oxocyclopentanecarboxylate

An α-alkylidation of cyclopentanone was achieved in two reaction steps in an overall yield of 20 to 79percent via a zinc chloride-catalyzed thioalkylation of the zinc enolate of methyl 2-oxocyclopentanecarboxylate (3) and subsequent saponification/desulfurization of the β-(phenylthio) ketone intermediates 5.For the saponification/desulfurization step DABCO proved to be the reagent of choice and superior to the use of alkali or magnesium halides. - Key Words: Zinc enolates, thioalkylation of / Cyclopentanones, α-alkylidene

Anodic Oxidation of Triphenylphosphine in the Presence of Enol Silyl Ethers or Enol Esters. Electrochemical One-step Preparation of 2-Oxocycloalkyltriphenylphosphonium Tetrafluoroborates

Electrochemical oxidation of triphenylphosphine in the presence of cyclic enol silyl ethers or enol esters gave 2-oxocycloalkyltriphenylphosphonium salts, which underwent the Wittig reaction with aldehydes to afford (E)-2-alkylidenecycloalkan-1-ones.

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.

α-Alkylation and α-alkylidenation of carbonyl compounds: Lewis acid-promoted phenylthioalkylation of o-silylated enolates

The O-silylated enolates of ketones, aldehydes, esters, and lactones can be phenylthioalkylated in the presence of Lewis acids; reductive or oxidative sulphur-removal gives the regiospecifically α-alkylated or alkylidenated carbonyl compounds.