16189-57-4

Usage

Type of compound

Saturated bicyclic alcohol

Industrial uses

Pharmaceutical and agrochemical industries (as a key building block for synthesis of various products)

Other applications

Solvent in the production of perfumes and flavors

Molecular structure

Cyclohexyl and cyclopentyl ring fused together

Specific properties

Unique molecular structure leading to specific reactivity

Toxicity

Low toxicity

Stability

High stability

Value in industrial applications

Versatile chemical

InChI:InChI=1/C11H20O/c12-11(8-4-5-9-11)10-6-2-1-3-7-10/h10,12H,1-9H2

Upstream product

• 120-92-3 cyclopentanone 
• 931-50-0 cyclohexylmagnesium bromide 
• 931-52-2 cyclohexylmagnesium iodide 

Downstream Products

• 253869-05-5 5-cyclohexyl-5-oxopentanal 
• 15972-18-6 5-cyclohexyl-5-pentanolide 
• 16189-56-3 cyclohexylcyclopentene 

Relevant academic research and scientific papers

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.

Studies in Alicyclic Compounds: Part VII - Koch-Haaf Carboxylation of 1-Cycloalkylcycloalkanols

The Koch-Haaf carboxylation (K-H-C) of 1-cycloalkylcyclopentanols (Ia and Ib) and 1-cycloalkylcyclohexanols (VIa and VIb) has been investigated.In the case of 1-cycloalkylcyclopentanols (Ia and Ib), K-H-C results in the formation of rearranged tertiary (30) bridgehead acids (Va and Vb) providing interesting examples of ring expansion reactions, whereas K-H-C of 1-cycloalkylcyclohexanols (VIa and VIb) furnishes the corresponding 30 carboxylic acids (VIIIa and VIIIb) in good yields.