15972-18-6

Upstream product

• 39858-70-3 2-cyclohexylcyclopentanone 
• 931-50-0 cyclohexylmagnesium bromide 
• 120-92-3 cyclopentanone 
• 16189-56-3 cyclohexylcyclopentene 
• 2969-81-5 Ethyl 4-bromobutyrate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 16189-57-4 1-cyclohexylcyclopentanol 
• 253869-05-5 5-cyclohexyl-5-oxopentanal 

Relevant academic research and scientific papers

Oxidation of the cyclopentanone and cyclohexanone alkyl derivatives in a pseudohomogeneous system without a phase transfer agent

The reaction of catalytic oxidation of C5-C12 alkyl- and cycloalkylcyclopentanones and -cyclohexanones to lactones in a pseudohomogeneous system without the participation of phase transfer agents was investigated. It was established that the catalytic systems prepared on the basis of molybdenum and tungsten blue (MeOnBrm, where Me = Mo, W, n = 1, 2, m = 2, 3) and H3PO4 deposited on powdered activated carbon AG-3 at 40-60°C, at 5-6 h duration exhibit a high selectivity in the reaction of nucleophilic addition of oxygen to the ketones with the formation of the valero- and caprolactones. Pleiades Publishing, Ltd., 2011.

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.

Cooperative Catalysis of Samarium Diiodide and Mercaptan in a Stereoselective One-pot Transformation of 5-oxopentanals into δ-lactones

(Matrix Presented) We demonstrate a general method for conversion of various 5-oxopentanals to substituted δ-lactones and 1-oxa-2-decalones by the synergistic catalysis of samarium diiodide and 2-propanethiol (or disulfide). The deliberate use of mercaptan is advantageous to facilitate the catalytic cycle. This method shows high stereoselectivities, and an enantioselective procedure is feasible by using the chiral mercaptan (1R,2S)-1-phenyl-2-(N-acetamido)propanethiol as a promoter.

Catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones

Pilot-plant syntheses of alkyl and cycloalkylcyclanones and their subsequent liquid-phase oxidation into lactones are described. Characteristics of resulting intermediates and target products are reported.

A Direct Synthesis of γ-, δ-, and ε-Lactones Utilizing SmI2-induced Barbier-type Reaction in the Presence of Hexamethylphosphoric Triamide (HMPA)

By using an efficient reduction system of SmI2-THF-HMPA, the coupling reaction of β-, γ-, or δ-bromoesters with carbonyl compounds was completed within a minute at room temperature affording γ-, δ-, or ε-lactones, respectively, in good yields.Cp2ZrCl2 was also found to be effective for the coupling with ketones.