160168-89-8

Basic information

• Product Name: Cyclohexanone, 2-methyl-5-(1-methylethyl)-, (5S)- (9CI)
• Synonyms: Cyclohexanone, 2-methyl-5-(1-methylethyl)-, (5S)- (9CI)
• CAS NO: 160168-89-8
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.24932
• Product Categories: ISOPROPYL
• Mol File: 160168-89-8.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cyclohexanone, 2-methyl-5-(1-methylethyl)-, (5S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 2-methyl-5-(1-methylethyl)-, (5S)- (9CI)(160168-89-8)
• EPA Substance Registry System: Cyclohexanone, 2-methyl-5-(1-methylethyl)-, (5S)- (9CI)(160168-89-8)

Safety Data

• Hazardous Substances Data: 160168-89-8(Hazardous Substances Data)

Synthetic route

(S)-p-mentha-6,8-dien-2-one (2244-16-8, 6485-40-1) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
With Rh/Al2O3; hydrogen In ethanol at 20℃; under 31503.2 Torr; for 3.5h; Autoclave;	99%
With 10% palladium on carbon; hydrogen	97%
With hydrogen; Lindlar's catalyst In ethanol
Multi-step reaction with 2 steps 1.1: water; potassium hydroxide; zinc / methanol / 73 h / Reflux 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 48 h / 20 °C 2.2: 0.33 h / 0 °C View Scheme

(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one (201012-68-2) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In hexane at 20℃; under 11251.1 Torr; for 12h; Sealed tube; Inert atmosphere;	98.9%
Stage #1: (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 48h; Stage #2: With Jones reagent In ethyl acetate at 0℃; for 0.333333h; Jones oxidation;	39.39 g

(-)-1-hydroxyneoisocarvomenthol (5745-59-5) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
With sulfuric acid Heating;

(-)-1-hydroxyisocarvomenthol (6711-53-1) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
With sulfuric acid

(1R,2S,4S)-4-isopropyl-1-methylcyclohexane-1,2-diol (39904-00-2) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
With sulfuric acid

Acetic acid (S)-5-isopropyl-2-methyl-cyclohex-1-enyl ester → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) + (5R)-5-isopropyl-2-methylcyclohexanone (127911-15-3)

Conditions	Yield
With cultured cells of Marchantia polymorpha; water at 25℃; for 5h; Yields of byproduct given. Title compound not separated from byproducts;

(1R,2S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol (39903-99-6) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / ethanol 2: aq. H2SO4 View Scheme

(1S,2S,4S)-limonene glycol (39904-04-6) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / ethanol 2: aq. H2SO4 / Heating View Scheme

(1S,2R,4S)-p-menth-8-ene-1,2-diol (39904-01-3) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / ethanol 2: aq. H2SO4 View Scheme

(1S,2S,3R,5R)-2,3-epoxy-5-isopropenyl-2-methylcyclohex-2-enol (39903-74-7) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 2: H2 / Raney-Ni / ethanol 3: aq. H2SO4 View Scheme

(1R,2S,4R,6S)-4-Isopropenyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-ol → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether 2: H2 / Raney-Ni / ethanol 3: aq. H2SO4 / Heating View Scheme

(1R,2R,4R,6S)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-ol (39903-82-7) → (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 2: H2 / Raney-Ni / ethanol 3: aq. H2SO4 View Scheme

(S)-p-mentha-6,8-dien-2-one (2244-16-8, 6485-40-1) → carvotanacetone (499-71-8) + (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) + (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one (201012-68-2)

Conditions	Yield
With hydrogen In tetrahydrofuran; water at 20℃; under 759.826 Torr; for 48h; Schlenk technique; Inert atmosphere;

chloro-trimethyl-silane (75-77-4) + (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) → 1-[(5S)-2-methyl-5-(methylethyl)cyclohex-1-enyloxy]-1,1-dimethyl-1-silaethane (1309660-00-1)

Conditions	Yield
With triethylamine; sodium iodide In acetonitrile at 20℃; for 4h; Inert atmosphere;	99%

(5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) → carvomenthide

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 48h; Inert atmosphere;	65.4%

(5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) → Ψ-diosphenol (54783-36-7) + (6S)-(+)-diosphenol + (6R)-(-)-diosphenol

Conditions	Yield
Stage #1: (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one With bromine In diethyl ether at -10℃; for 7h; Stage #2: With sodium hydroxide In tetrahydrofuran at -10℃; for 0.833333h;	A 12% B n/a C n/a

(5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) → (5R)-2-chloro-2-methyl-5-isopropylcyclohexanone

Conditions	Yield
With sulfuryl dichloride In tetrachloromethane

(5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) → (5S)-2-chloro-2-methyl-5-isopropylcyclohexanone + (5S)-2-chloro-2-methyl-5-isopropylcyclohexanone

Conditions	Yield
With sulfuryl dichloride In tetrachloromethane optical yield given as %de;

(5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) → (2S,5S)-2-methyl-5-(methylethyl)-2-prop-2-enylcyclohexan-1-one (1309659-99-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; sodium iodide / acetonitrile / 4 h / 20 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); (S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-1,3-oxazol; tetrabutylammonium triphenyldifluorosilicate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere View Scheme

(5S)-2-methyl-5-(methylethyl)cyclohexan-1-one (160168-89-8) → (2S,5S)-2-methyl-5-(methylethyl)-2-prop-2-enylcyclohexan-1-one (1309659-99-1) + (2R,5S)-2-methyl-5-(methylethyl)-2-prop-2-enylcyclohexan-1-one (1309660-01-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; sodium iodide / acetonitrile / 4 h / 20 °C / Inert atmosphere 2.1: methyllithium / tetrahydrofuran; 1,2-dimethoxyethane / 1 h / -40 °C / Inert atmosphere 2.2: 19 h / -50 °C / Inert atmosphere 2.3: Inert atmosphere View Scheme

Upstream product

• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 201012-68-2 (5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one 
• 39903-82-7 (1R,2R,4R,6S)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-ol 
• 39903-74-7 (1S,2S,3R,5R)-2,3-epoxy-5-isopropenyl-2-methylcyclohex-2-enol 
• 39904-01-3 (1S,2R,4S)-p-menth-8-ene-1,2-diol 
• 39904-04-6 (1S,2S,4S)-limonene glycol 
• 39903-99-6 (1R,2S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol 
• 39904-00-2 (1R,2S,4S)-4-isopropyl-1-methylcyclohexane-1,2-diol 
• 6711-53-1 (-)-1-hydroxyisocarvomenthol 
• 5745-59-5 (-)-1-hydroxyneoisocarvomenthol 

Downstream Products

• 1309660-00-1 1-[(5S)-2-methyl-5-(methylethyl)cyclohex-1-enyloxy]-1,1-dimethyl-1-silaethane 
• 1309659-99-1 (2S,5S)-2-methyl-5-(methylethyl)-2-prop-2-enylcyclohexan-1-one 
• 1309660-01-2 (2R,5S)-2-methyl-5-(methylethyl)-2-prop-2-enylcyclohexan-1-one 
• 606490-81-7 carvomenthide 
• 54783-36-7 ξ-diosphenol 
• 468722-70-5 (6S)-(+)-diosphenol 
• 468722-70-5 (6R)-(-)-diosphenol 

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