60046-49-3

Basic information

• Product Name: 2,2,6-Trimethyl-1,4-cyclohexandion
• Synonyms: 2,2,6-Trimethyl-1,4-cyclohexandion;(R)-2,2,6-trimethyl-1,4-cyclohexanedione
• CAS NO: 60046-49-3
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.21
• Mol File: 60046-49-3.mol
• Article Data: 36

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane; Methanol; Ethyl Acetate
• CAS DataBase Reference: 2,2,6-Trimethyl-1,4-cyclohexandion(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,6-Trimethyl-1,4-cyclohexandion(60046-49-3)
• EPA Substance Registry System: 2,2,6-Trimethyl-1,4-cyclohexandion(60046-49-3)

Safety Data

• Hazardous Substances Data: 60046-49-3(Hazardous Substances Data)

Usage

Uses

(6R)-Levodione is an intermediate used in the synthesis of Xanthoxin (X742550), which is a growth inhibitor in plants.

Purification Methods

It is obtained from fermentation and is purified by recrystallisation from diisopropyl ether. [ORD: Leuenberger et al. Helv Chim Acta 59 1832 1976.] The racemate has m 65-67o, and the 4-(4-phenyl)semicarbazone has m 218-220o (from CH2Cl2/MeOH) [Isler et al. Helv Chim Acta 39 2041 1956, Beilstein 7 IV 2032.]

Upstream product

• 952-92-1 1-Benzyl-1,4-dihydronicotinamide 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 

Downstream Products

• 20548-02-1 (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one 
• 130584-00-8 Acetic acid (Z)-5-[(1R,4R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-pent-2-en-4-ynyl ester 
• 130583-96-9 Acetic acid (Z)-5-[(4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2,2,6-trimethyl-cyclohexyl]-3-methyl-pent-2-en-4-ynyl ester 
• 130584-04-2 (+)-1(Z)-(1R,4R,6S)-4-tert-butyldimethylsiloxy-1-(5-hydroxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexanol 
• 130584-04-2 (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-((Z)-5-hydroxy-3-methyl-pent-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol 
• 130646-72-9 (-)-1(Z)-(1S,4R,6R)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol 
• 130583-99-2 (+)-1(Z)-(1R,4R,6S)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol 
• 130646-73-0 (-)-1(Z)-(1R,4R,6R)-1-(5-acetoxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexan-1,4-diol 
• 26533-74-4 Acetic acid (Z)-5-((1S,6R)-1-hydroxy-2,2,6-trimethyl-4-oxo-cyclohexyl)-3-methyl-pent-2-en-4-ynyl ester 
• 130694-70-1 Acetic acid (Z)-5-((1R,6S)-1-hydroxy-2,2,6-trimethyl-4-oxo-cyclohexyl)-3-methyl-pent-2-en-4-ynyl ester 
• 130694-58-5 Acetic acid (Z)-5-((1R,6R)-1-hydroxy-2,2,6-trimethyl-4-oxo-cyclohexyl)-3-methyl-pent-2-en-4-ynyl ester 
• 130694-62-1 (-)-(4R,5R)-methyl dihydroabscisate 
• 130694-54-1 (+)-(4S,5S)-methyl dihydroabscisate 
• 130694-68-7 (1'S,2'R)-2',3'-dihydro-abscisic acid methyl ester 

Relevant articles and documents

Photoenzymatic reduction of C=C double bonds

A simplified procedure for cell-free biocatalytic reductions of conjugated C=C double bonds using old yellow enzymes (OYEs) is reported. Instead of indirectly regenerating YqjM (an OYE homologue from B. subtilis) or NemA (N-ethylmaleimide reductase from E

A robust and stereocomplementary panel of ene-reductase variants for gram-scale asymmetric hydrogenation

We report an engineered panel of ene-reductases (ERs) from Thermus scotoductus SA-01 (TsER) that combines control over facial selectivity in the reduction of electron deficient C[dbnd]C double bonds with thermostability (up to 70 °C), organic solvent tolerance (up to 40 % v/v) and a broad substrate scope (23 compounds, three new to literature). Substrate acceptance and facial selectivity of 3-methylcyclohexenone was rationalized by crystallisation of TsER C25D/I67T and in silico docking. The TsER variant panel shows excellent enantiomeric excess (ee) and yields during bi-phasic preparative scale synthesis, with isolated yield of up to 93 % for 2R,5S-dihydrocarvone (3.6 g). Turnover frequencies (TOF) of approximately 40 000 h?1 were achieved, which are comparable to rates in hetero- and homogeneous metal catalysed hydrogenations. Preliminary batch reactions also demonstrated the reusability of the reaction system by consecutively removing the organic phase (n-pentane) for product removal and replacing with fresh substrate. Four consecutive batches yielded ca. 27 g L?1 R-levodione from a 45 mL aqueous reaction, containing less than 17 mg (10 μM) enzyme and the reaction only stopping because of acidification. The TsER variant panel provides a robust, highly active and stereocomplementary base for further exploitation as a tool in preparative organic synthesis.

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.