Levodione

Base Information

• Chemical Name: Levodione
• CAS No.: 60046-49-3
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• DSSTox Substance ID: DTXSID601335381
• Nikkaji Number: J946.010A
• Wikidata: Q27159134
• Mol file: 60046-49-3.mol

Synonyms:dihydrooxoisophorone;DOIP cpd;levodione

Chemical Property of Levodione

Chemical Property:

• PSA: 34.14000
• LogP: 1.58070
• Solubility.: Dichloromethane; Methanol; Ethyl Acetate
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 204

Purity/Quality:

99%min ^*data from raw suppliers

(6R)-Levodione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(=O)CC(C1=O)(C)C
• Isomeric SMILES: C[C@@H]1CC(=O)CC(C1=O)(C)C
• Uses: (6R)-Levodione is an intermediate used in the synthesis of Xanthoxin (X742550), which is a growth inhibitor in plants.

Technology Process of Levodione

There total 9 articles about Levodione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

2,6,6-trimethyl-2-cyclohexene-1,4-dione (1125-21-9) → (4S)-hydroxy-(6R)-2,2,6-trimethylcyclohexanone (55058-51-0) + (6R)-levodione (60046-49-3)

Guidance literature:

With D-glucose; Saccharomyces cerevisiae (baker's yeast, Fermix(R)); oxygen; In ethanol; for 48h; Further Variations:; conc. of educt and reagents; Product distribution; Kinetics;

DOI:10.1002/adsc.200505024

Reference yield: 81.1%

2,6,6-trimethyl-2-cyclohexene-1,4-dione (1125-21-9) → (6R)-levodione (60046-49-3) + (6S)-2,2,6-trimethylcyclohexane-1,4-dione (60686-83-1)

Guidance literature:

With recombinant old yellow enzyme from Bacillus subtilis; water; chromium; Flavin mononucleotide; In aq. buffer; at 21 ℃; for 4h; pH=6.5; stereoselective reaction; Glovebox; Darkness; Inert atmosphere; Enzymatic reaction;

DOI:10.1002/cbic.201900685

Reference yield: 80.0%

2,6,6-trimethyl-2-cyclohexene-1,4-dione (1125-21-9) → (6R)-levodione (60046-49-3)

Guidance literature:

With D-glucose; YqjM-RBS-GDH; NADPH; In aq. buffer; at 30 ℃; for 12h; pH=7.5; enantioselective reaction; Ionic liquid; Green chemistry; Enzymatic reaction;

DOI:10.1039/d1gc00372k

upstream raw materials:

2,6,6-trimethyl-2-cyclohexene-1,4-dione

1-Benzyl-1,4-dihydronicotinamide

Downstream raw materials:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

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

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

(+)-1(Z)-(1R,4R,6S)-4-tert-butyldimethylsiloxy-1-(5-hydroxy-3-methylpent-3-en-1-ynyl)-2,2,6-trimethylcyclohexanol

Refernces

• 1、 Luan, Pengqian,Liu, Yunting,Li, Yongxing,Chen, Ran,Huang, Chen,Gao, Jing,Hollmann, Frank,Jiang, Yanjun. "Aqueous chemoenzymatic one-pot enantioselective synthesis of tertiary α-aryl cycloketonesviaPd-catalyzed C-C formation and enzymatic C=C asymmetric hydrogenation". supporting information. p. 1960 - 1964. Retrieved 2021/03/26.
• 2、 Cleary, Sarah E.,Joseph Srinivasan, Shiny,Paul, Caroline E.,Ramirez, Miguel A.,Reeve, Holly A.,Vincent, Kylie A.. "E. coli Nickel-Iron Hydrogenase 1 Catalyses Non-native Reduction of Flavins: Demonstration for Alkene Hydrogenation by Old Yellow Enzyme Ene-reductases**". supporting information. p. 13824 - 13828. Retrieved 2021/05/13.