60686-83-1

Basic information

• Product Name: (6S)-2,2,6-trimethylcyclohexane-1,4-dione
• Synonyms: (6S)-2,2,6-trimethylcyclohexane-1,4-dione
• CAS NO: 60686-83-1
• Molecular Weight: 154.209
• Mol File: 60686-83-1.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: (6S)-2,2,6-trimethylcyclohexane-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (6S)-2,2,6-trimethylcyclohexane-1,4-dione(60686-83-1)
• EPA Substance Registry System: (6S)-2,2,6-trimethylcyclohexane-1,4-dione(60686-83-1)

Safety Data

• Hazardous Substances Data: 60686-83-1(Hazardous Substances Data)

Upstream product

• 20548-03-2 4-hydroxy-3,3,5-trimethylcyclohexan-1-one 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 952-92-1 1-Benzyl-1,4-dihydronicotinamide 

Relevant articles and documents

Characterization of xenobiotic reductase A (XenA): Study of active site residues, substrate spectrum and stability

Xenobiotic reductase A (XenA) has broad catalytic activity and reduces various α,β-unsaturated and nitro compounds with moderate to excellent stereoselectivity. Single mutants C25G and C25V are able to reduce nitrobenzene, a non-active substrate for the wild type, to produce aniline. Total turnover is dominated by chemical rather than thermal instability. The Royal Society of Chemistry 2010.

Metals in Biotechnology: Cr-Driven Stereoselective Reduction of Conjugated C=C Double Bonds

Elemental metals are shown to be suitable sacrificial electron donors to drive the stereoselective reduction of conjugated C=C double bonds using Old Yellow Enzymes as catalysts. Both direct electron transfer from the metal to the enzyme as well as mediated electron transfer is feasible, although the latter excels by higher reaction rates. The general applicability of this new chemoenzymatic reduction method is demonstrated, and current limitations are outlined.

Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond Functionalization

In this study, we combined photo-organo redox catalysis and biocatalysis to achieve asymmetric C–H bond functionalization of simple alkane starting materials. The photo-organo catalyst anthraquinone sulfate (SAS) was employed to oxyfunctionalise alkanes to aldehydes and ketones. We coupled this light-driven reaction with asymmetric enzymatic functionalisations to yield chiral hydroxynitriles, amines, acyloins and α-chiral ketones with up to 99 % ee. In addition, we demonstrate functional group interconversion to alcohols, esters and carboxylic acids. The transformations can be performed as concurrent tandem reactions. We identified the degradation of substrates and inhibition of the biocatalysts as limiting factors affecting compatibility, due to reactive oxygen species generated in the photocatalytic step. These incompatibilities were addressed by reaction engineering, such as applying a two-phase system or temporal and spatial separation of the catalysts. Using a selection of eleven starting alkanes, one photo-organo catalyst and 8 diverse biocatalysts, we synthesized 26 products and report for the model compounds benzoin and mandelonitrile > 97 % ee at gram scale.