165105-99-7

Upstream product

• 13482-22-9 4-hydroxycyclohexanone 
• 3282-30-2 pivaloyl chloride 
• 556-48-9 1,4-Cyclohexanediol 
• 22428-87-1 4,4-ethylenedioxycyclohexan-1-ol 

Downstream Products

• 945843-14-1 15-[(4-methoxybenzyl)oxy]-7,11,18,21-tetraoxatrispiro[5.2.2.5.2.2]henicos-3-yl pivalate 
• 945843-28-7 15-[(4-methoxybenzyl)oxy]-7,11,18,21-tetraoxatrispiro[5.2.2.5.2.2]henicosan-3-ol 
• 945843-35-6 15-[(4-methoxybenzyl)oxy]-7,11,18,21-tetraoxatrispiro[5.2.2.5.2.2]henicosan-3-one 
• 1373308-22-5 (+/-)-2,2-dimethylpropionic acid 4,4-dimethoxycyclohexyl ester 
• 931-71-5 cis-1,4-cyclohexanediol 
• 120-80-9 benzene-1,2-diol 
• 209472-53-7 2,2-Dimethyl-propionic acid 3-methyl-4-oxo-cyclohexyl ester 

Relevant academic research and scientific papers

A formal synthesis of vinigrol

Two key reactions in a rapid assembly of the tricyclic core of vinigrol are a stereoselective Claisen rearrangement and an intramolecular Diels-Alder reaction. The method paves the way for a total synthesis of this synthetically challenging and biologically interesting natural product. Copyright

Synthesis and NMR spectroscopic conformational analysis of esters of 4-hydroxy-cyclohexanone - The more polar the molecule the more stable the axial conformer

The esters of 4-hydroxy-cyclohexanone and a series of carboxylic acids R-COOH with R of different electronic and steric influence (R=Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, sec-Bu, t-Bu, CF3, CH2Cl, CHCl 2, CCl3, CH2Br, CHBr2, and CBr 3) were synthesized and the conformational equilibria studied by 1H and 13C NMR spectroscopy at 103 K and at 295 K, respectively. The geometry of optimized structures of the axial/equatorial chair conformers was computed at the ab initio MO and DFT levels of theory. Only one preferred conformation was obtained for the axial and the equatorial conformer as well. When comparing the conformational equilibria of the cyclohexanone esters with those of the corresponding cyclohexyl esters a certain polarity contribution of the cyclohexanone framework was revealed, which is independent of the substituent effects and increases the stability of the axial conformers by a constant amount.

Oligospiroketals as novel molecular rods

A modular approach for the synthesis of molecular rods based on oligospiroketals has been developed. The strategy relies on different terminal and intermediate segments, which are joined by ketal formation between ketones and diols. For this purpose it was necessary to develop a new ketalization method to circumvent some problems related with the established methods. The terminal segments are either derived from 4-piperidinone or from 4-oxocyclohexane carboxylic acid whereas the intermediate segments rest on pentaerythritol and cyclohexane-1,4-dione. A series of trispiro (14-18), hexaspiro (19) and nonaspiro (20) compounds have been prepared and characterized. From these we realized that it is imperative to use solubility enhancing groups if more than seven rings are joined.

The synthesis of (±)-wilforonide

The first synthesis of (±)-wilforonide has been completed in ten steps from commercially available starting materials. A high-yielding monomethylation of a reactive ketone enolate, a regioselective α-annulation of an unactivated α-substituted cyclohexanone, and a selective hydrogenation of the resulting unsaturated keto ester were key steps in the synthesis.

Enantioselective deprotonation of protected 4-hydroxycyclohexanones

A series of derivatives of 4-hydroxycyclohexanone (1a-g) with the hydroxy group protected as a silyl ether (1a,b), ether (1d,g), an acetal (1c), or an ester (1e,f) were deprotonated with chiral, optically pure, lithium amides 3-9. The resulting non-racemic enolates were trapped as enol acetates. The enantioselectivity of deprotonation was up to 74percent ee.