2,6,6-Trimethyl-5beta-isopropenyl-2-cyclohexene-1-one

Base Information

• Chemical Name: 2,6,6-Trimethyl-5beta-isopropenyl-2-cyclohexene-1-one
• CAS No.: 179259-37-1
• Molecular Formula: C12H18O
• Molecular Weight: 178.274
• DSSTox Substance ID: DTXSID70455361
• Nikkaji Number: J1.046.475G
• Wikidata: Q82277320
• Mol file: 179259-37-1.mol

Synonyms:179259-37-1;2,6,6-Trimethyl-5beta-isopropenyl-2-cyclohexene-1-one;CTK0E3318;SCHEMBL17385137;DTXSID70455361;(5s)-5-isopropenyl-2,6,6-trimethylcyclohex-2-en-1-one

Chemical Property of 2,6,6-Trimethyl-5beta-isopropenyl-2-cyclohexene-1-one

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 178.135765193
• Heavy Atom Count: 13
• Complexity: 282

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC(C(C1=O)(C)C)C(=C)C
• Isomeric SMILES: CC1=CC[C@H](C(C1=O)(C)C)C(=C)C

Technology Process of 2,6,6-Trimethyl-5beta-isopropenyl-2-cyclohexene-1-one

There total 2 articles about 2,6,6-Trimethyl-5beta-isopropenyl-2-cyclohexene-1-one 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: 97.0%

(R)-6-methylcarvone (138812-34-7) + methyl iodide (74-88-4) → (+)-(5S)-5-isopropenyl-2,6,6-trimethylcyclohex-2-enone (179259-37-1)

Guidance literature:

(R)-6-methylcarvone; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jacs.0c05042

Reference yield:

(R)-Carvone (6485-40-1,2244-16-8) + methyl iodide (74-88-4) → (6S,5R)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one (91781-46-3) + (6R,5R)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one (91840-35-6) + (+)-(5S)-5-isopropenyl-2,6,6-trimethylcyclohex-2-enone (179259-37-1)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 10h; optical yield given as %de;

DOI:10.1134/S1070428011020047

Reference yield: 93.0%

(+)-(5S)-5-isopropenyl-2,6,6-trimethylcyclohex-2-enone (179259-37-1) → 5R-5-(3-chloroprop-1-en-2-yl)-2,6,6-trimethyl-2-cyclohexene-1-one

Guidance literature:

With tert-butylhypochlorite; silica gel; In hexane; at -30 - 20 ℃; for 0.666667h;

upstream raw materials:

(R)-6-methylcarvone

methyl iodide

(R)-Carvone

Downstream raw materials:

(S)-5-Isopropenyl-2,6,6-trimethyl-1-vinyl-cyclohex-2-enol

(R)-5-(1-Bromomethyl-vinyl)-2,6,6-trimethyl-cyclohex-2-enone

(1S,5S)-5-Isopropenyl-2,6,6-trimethyl-1-phenethyl-cyclohex-2-enol

(+)-(5S)-5-isopropenyl-2,3,4,4-tetramethylcyclohex-2-en-1-one

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