(-)-Carvomenthone

Base Information

• Chemical Name: (-)-Carvomenthone
• CAS No.: 13163-73-0
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• UNII: 9089X37X82
• DSSTox Substance ID: DTXSID601244235
• Nikkaji Number: J247.017I
• Metabolomics Workbench ID: 46779
• Mol file: 13163-73-0.mol

Synonyms:carvomenthone;p-menthan-2-one;tetrahydrocarvone

Chemical Property of (-)-Carvomenthone

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC(CC1=O)C(C)C
• Isomeric SMILES: C[C@H]1CC[C@@H](CC1=O)C(C)C

Technology Process of (-)-Carvomenthone

There total 37 articles about (-)-Carvomenthone 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: 88.0%

(R,E)-4-[(tert-butyldimethylsilyl)oxy]-4-[(1S,3S,6R)-6-isopropyl-3-methyl-2-oxocyclohexyl]-3-methylbut-2-en-1-yl diethyl phosphate → (-)-carvomenthone (13163-73-0)

Guidance literature:

(R,E)-4-[(tert-butyldimethylsilyl)oxy]-4-[(1S,3S,6R)-6-isopropyl-3-methyl-2-oxocyclohexyl]-3-methylbut-2-en-1-yl diethyl phosphate; With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 2h;

With water; Acidic aq. solution;

DOI:10.1021/ol902854t

Reference yield: 78.0%

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → (-)-carvomenthone (13163-73-0)

Guidance literature:

(S)-p-mentha-6,8-dien-2-one; With 2-methoxy-ethanol; nickel dichloride; zinc; at 40 ℃; for 6h; ultra sound;

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 72h;

DOI:10.1016/j.tetlet.2005.01.080

Reference yield: 53.0%

carvacrol (499-75-2) → methyl-2 isopropyl-5 cyclohexanone (499-70-7,3901-91-5,5206-83-7,7065-48-7,13163-73-0,13163-74-1,59471-80-6,116562-19-7,127911-15-3)

Guidance literature:

With C₃₃H₄₉ClNRh; hydrogen; In 2,2,2-trifluoroethanol; water; at 70 ℃; for 24h; under 60006 Torr; Autoclave;

DOI:10.1021/jacs.5b05868

upstream raw materials:

(1S,2S,4S)-(+)-carvomenthol

(-)neocarvomenthol

(2R,5S)-(-)-carvomenthone

sodium ethanolate

Downstream raw materials:

(2R,5S)-(-)-carvomenthone

(1S,2S,4S)-(+)-carvomenthol

(-)neocarvomenthol

(-)-carvomenthone oxime

Refernces

• 1、 Wei, Yu,Rao, Bin,Cong, Xuefeng,Zeng, Xiaoming. "Highly Selective Hydrogenation of Aromatic Ketones and Phenols Enabled by Cyclic (Amino)(alkyl)carbene Rhodium Complexes". supporting information. p. 9250 - 9253. Retrieved 2015/08/11.
• 2、 Padhi, Santosh Kumar,Bougioukou, Despina J.,Stewart, Jon D.. "Site-saturation mutagenesis of tryptophan 116 of saccharomyces pastorianus old yellow enzyme uncovers stereocomplementary variants". experimental part. p. 3271 - 3280. Retrieved 2009/07/30.