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 trans (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone 
• 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 

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

Aqueous chemoenzymatic one-pot enantioselective synthesis of tertiary α-aryl cycloketonesviaPd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation

An aqueous chemoenzymatic cascade reaction combining Pd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation (AH) was developed for enantioselective synthesis of tertiary α-aryl cycloketones in good yields and excellent enantioselectivities. The stereopreference of the enzyme in AH of α-aryl cyclohexenones was studied. An enantiocomplementary enzyme was obtained by site-directed mutation.

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.