2,6,6-Trimethyl-2-cyclohexene-1,4-dione supplier

Name
2,6,6-Trimethyl-2-cyclohexene-1,4-dione
EINECS 214-406-2
CAS No. 1125-21-9
Article Data59
CAS DataBase
Density 1.02 g/cm³
Solubility
Melting Point 26-28 °C(lit.)
Formula C₉H₁₂O₂
Boiling Point 214.2 °C at 760 mmHg
Molecular Weight 152.193
Flash Point 84.9 °C
Transport Information UN 2811 6.1/PG 3
Appearance clear yellow to orange liquid or low melting solid
Safety 26-36/37-37/39
Risk Codes 22-43-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms 2,6,6-Trimethyl-2-cyclohexen-1,4-dione;2,6,6-Trimethylcyclohex-2-ene-1,4-dione;3,5,5-Trimethyl-2-cyclohexene-1,4-dione;4-Ketoisophorone;4-Oxo-a-isophorone;4-Oxoisophorone;6-Oxoisophorone;Ketoisophorone;Oxoisophorone;Oxopholone;Oxophorone;keto-Isophorone;Teaketone;
PSA 34.14000
LogP 1.50080

Synthetic route

: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With 2,5-Dimethyl-1,4-benzoquinone In toluene at 80℃; Reagent/catalyst; Solvent; Temperature;	98.98%
With chromium(VI) oxide
With chromium(VI) oxide; sulfuric acid In acetone
With chromic acid
With sodium anthraquinone-2-sulfonate; oxygen In water at 30℃; Irradiation;

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With diisobutyl ketone; oxygen; 1,4-diaza-bicyclo[2.2.2]octane at 40℃; for 5h;	93%
With (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; oxygen; triethylamine In 1,2-dimethoxyethane; water for 9h; Ambient temperature;	92%
	62.8%

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; cobalt acetylacetonate In acetone at 28℃; for 15h; Solvent; Concentration; Temperature;	79%
With tert.-butylhydroperoxide; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; water In neat (no solvent) at 20℃; for 24h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Temperature; Sealed tube; regioselective reaction;	78%
With tert.-butylhydroperoxide; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In water at 20℃; for 24h; Catalytic behavior; Concentration; Temperature; Solvent; Time;	78%

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

A: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

C: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions

Conditions	Yield
With Tri-n-octylamine; sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 70℃; for 2h; pH=1.5 - 2; Temperature; Reagent/catalyst;	A 8% B 24% C 67%
With Tri-n-octylamine; sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 90℃; for 2h; pH=1.5 - 2; Catalytic behavior; Reagent/catalyst; Temperature;	A 15% B 46% C 16%
With sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 80℃; for 2h; pH=1.5 - 2; Temperature;	A 22% B 5% C 13%
With oxygen; triethylamine; iron tetrasulfophthalocyanine-TiO2 In dimethyl sulfoxide at 60℃; under 1500.12 Torr; for 24h;	A 10 % Chromat. B 57 % Chromat. C 21 % Chromat.

...Expand

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

B: 96493-78-6
2,3,6,7-tetrahydro-2,2,6,6-tetramethylanthracene-1,4,5,8-tetrone

Conditions

Conditions	Yield
With potassium dichromate; air; phosphomolybdic acid; copper(II) sulfate at 90 - 95℃; for 100h;	A 56% B n/a
With potassium dichromate; air; phosphpmolybdic acid; copper(II) sulfate at 90 - 95℃; for 100h; basic treatment during workup;
With potassium dichromate; phosphomolybdic acid; oxygen; copper(II) sulfate 1. 100 deg C, 100 hours; Multistep reaction;

: 518316-69-3
(S)-4-Hydroxy-3,5,5-trimethyl-4-(toluene-4-sulfonylmethyl)-cyclohex-2-enone

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; for 0.3h;	54%

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 10276-21-8
isophorone oxide

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

C: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions

Conditions	Yield
With [2,2]bipyridinyl; silver(I) acetate; lithium perchlorate In water; acetonitrile electrochemical oxidation;
With N-hydroxyphthalimide; oxygen at 60℃; for 10h;

...Expand

: 896107-70-3
9-hydroxymegastigma-4,7-dien-3-one

A: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

B: 20547-99-3
2,6,6-trimethyl-1,4-cyclohexanedione

C: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

D: 13215-88-8
4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

E: megastigmatrienone

Conditions

Conditions	Yield
In water Heating; pH=1;

...Expand

: 127-41-3
alpha-ionone

A: 15764-81-5
dehydrovomifoliol

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

C: 79734-43-3
3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one

Conditions

Conditions	Yield
With t-butyl chromate In tert-butyl alcohol; benzene at 60℃;	A 700 mg B 105 mg C 750 mg

...Expand

: 23526-45-6, 24427-77-8, 50763-72-9, 50763-73-0
6,9-dihydroxymegastigma-4,7-dien-3-one

A: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

B: 697-82-5
2,3,5-trimethylphenol

C: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
Heating; pH=1;

...Expand

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 20547-99-3
2,6,6-trimethyl-1,4-cyclohexanedione

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

C: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

D: 3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

Conditions

Conditions	Yield
In water at 28℃; for 96h; Aspergillus niger, culture broth;
In water at 28℃; for 96h; Aspergillus niger, culture broth; Yield given. Yields of byproduct given;
In water at 28℃; for 96h; Aspergillus niger, culture broth; Yield given;

...Expand

: (-)-3-Hydroxy-2,5-dioxo-1,1,3-trimethyl-cyclohexan

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With sulfuric acid

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 56621-35-3
3-formyl-5,5-dimethyl-2-cycolohexen-1-one

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With methanesulfonic acid; oxygen; molybdovanadophosphate on active carbon In toluene at 80℃; under 760 Torr; for 20h; Product distribution; regioselectivity of the aerobic oxidation, effect of the pore size of supports, or without support at various temperatures;
With phosphomolybdic acid; potassium tert-butylate; oxygen In dimethyl sulfoxide at 115℃; for 8h; Product distribution; Further Variations:; Reagents; reaction time;	A 1.9 % Chromat. B 88.4 % Chromat.
With N-hydroxyphthalimide; oxygen; copper dichloride In acetonitrile at 100℃; under 9000.9 Torr; for 3h; Autoclave;

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

A: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

B: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

C: β-isophorone oxide

D: 5-hydroxy-4,4,6-trimethyl-7-oxa-bicyclo[4.1.0]heptan-2-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; silica gel; titanium(IV) oxide In ethylbenzene at 79.85℃; for 0.208333h; Product distribution; Further Variations:; Catalysts; time; Isomerization; oxidation;

...Expand

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

CuSO4 *5H2 O: CuSO4 *5H2 O

H3 [P(Mo3 O10)4 ]*H2 O: H3 [P(Mo3 O10)4 ]*H2 O

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
MoO3 In hexane; toluene

...Expand

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 10276-21-8
isophorone oxide

B: 56621-35-3
3-formyl-5,5-dimethyl-2-cycolohexen-1-one

C: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With N-hydroxyphthalimide; oxygen; copper(II) sulfate In acetonitrile at 75℃; under 9000.9 Torr; for 5h; Autoclave;

...Expand

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 10276-21-8
isophorone oxide

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With N-hydroxyphthalimide; oxygen; calcium chloride In acetonitrile at 75℃; under 9000.9 Torr; for 5h; Autoclave;
With N-hydroxyphthalimide; oxygen In acetonitrile at 110℃; under 9000.9 Torr; for 5h; Catalytic behavior; Temperature; Time; Concentration;

: (S)-4-hydroxy-3,5,5-trimethyl-4-[(3E,5E,7E,9E,11E,13E,15E)-3,7,12,16-tetramethyl-2-oxo-18-((R)-2,6,6-trimethyl-4-(triethylsilyloxy)cyclohex-1-en-1-yl)octadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-yl]cyclohex-2-enone

A: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

B: (all-E)-(3R)-Triophaxanthin

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride Inert atmosphere;

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

A: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen at 70℃; for 12h; Reagent/catalyst;
With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen at 70℃; for 12h;

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

A: 28750-52-9
2-hydroxy-4,4,6-trimethylcyclohexa-2,5-diene-1-one

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

C: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions

Conditions	Yield
With water; oxygen; triethylamine; acetylacetone In acetone at 21℃; for 18h; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Overall yield = 65.4 %;

...Expand

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

A: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

B: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions

Conditions	Yield
With pyridine; iron(III)-acetylacetonate; oxygen at 59.99℃; under 760.201 Torr; Kinetics; Activation energy; Temperature; Pressure; Inert atmosphere;

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 10276-21-8
isophorone oxide

B: 56621-35-3
3-formyl-5,5-dimethyl-2-cycolohexen-1-one

C: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

D: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; cetyltrimethylammonim bromide; L-proline; copper dichloride In water at 80℃; for 24h; Reagent/catalyst;
With tert.-butylhydroperoxide; N-hydroxyphthalimide; Cu3Al(OH)2(7+)*3.5CO3(2-) In acetonitrile at 90℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature;

...Expand

: 4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions

Conditions	Yield
With Cm-ADH10 at 40℃; for 6h; Enzymatic reaction;	46 mg

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

B: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

C: 3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

D: 4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

Conditions

Conditions	Yield
With perfluorodecanoic acid; CYP102A1 from Bacillus megaterium; oxygen; NADPH; bovine liver catalase In dimethyl sulfoxide at 30℃; for 20h; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction; stereoselective reaction;

...Expand

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

B: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

C: 3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

Conditions

Conditions	Yield
Stage #1: 3,5,5-Trimethylcyclohex-2-en-1-one With sodium hydroxide In water at 0 - 2℃; for 0.166667h; Stage #2: With dihydrogen peroxide In water at 0 - 2℃; for 6h;	A n/a B 12 mg C n/a

...Expand

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

A: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

B: 4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

C: 4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

Conditions

Conditions	Yield
With Peroxygenase from Chaetomium globosum; dihydrogen peroxide In aq. phosphate buffer at 30℃; for 0.5h; pH=7; Catalytic behavior; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	A n/a B n/a C n/a

...Expand

: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

A: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

B: 4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

Conditions

Conditions	Yield
With Peroxygenase from Chaetomium globosum; dihydrogen peroxide In aq. phosphate buffer at 30℃; for 1h; pH=7; Catalytic behavior; Reagent/catalyst; Resolution of racemate; Enzymatic reaction; enantioselective reaction;

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 107-13-1
acrylonitrile

: (1R,2R,4S)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carbonitrile

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-methylaminopropylated silica gel In tetrahydrofuran; hexane at -70 - 20℃; Michael reaction;	100%
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -50℃; for 0.333333h; Stage #2: acrylonitrile In tetrahydrofuran; hexane at -50 - 20℃; for 3h;	99%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 20547-99-3
2,6,6-trimethyl-1,4-cyclohexanedione

Conditions

Conditions	Yield
With phenylsilane; isopropyl alcohol; Mn(dpm)3 at 23℃;	99%
With triethanolamine; [RuII(2,2′-bipyrazyl)2(4,4′-dichloro-2,2′-bipyridyl)]Cl2; thermophilic Old Yellow Enzyme; paraquat dichloride In ethanol; water at 20℃; for 4h; pH=8; Reagent/catalyst; Solvent; Time; pH-value; UV-irradiation;	88%
With acetic acid; zinc

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 20548-02-1
trans (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone

Conditions

Conditions	Yield
With hydrogen; Ra-Ni In methanol at 25℃; under 825.07 Torr; for 8h;	98.1%
With hydrogen; Raney/Ni In ethanol at 20℃; under 5171.62 Torr; for 72h;

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 107-21-1
ethylene glycol

: 14203-64-6
7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one

Conditions

Conditions	Yield
With phenylphosphonate In benzene for 24h;	96.7%
With toluene-4-sulfonic acid; trimethyl orthoformate In dichloromethane for 4h; Heating;	87%
With toluene-4-sulfonic acid In benzene for 10h; Heating;	73%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 108-24-7
acetic anhydride

: 7479-28-9
2,3,5-trimethyl-1,4-hydroquinone diacetate

Conditions

Conditions	Yield
at 60℃; for 9h; Temperature; Molecular sieve;	96.5%
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione; acetic anhydride; methanetrisulfonic acid at 25 - 100℃; for 3.5 - 24h; Stage #2: With sodium carbonate at 20℃; Product distribution / selectivity;	0%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 149-73-5
trimethyl orthoformate

: 4-Methoxy-2,6,6-trimethyl-cyclohexa-2,4-dienone

Conditions

Conditions	Yield
With hydrogenchloride In methanol Heating;	95%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 623-47-2
propynoic acid ethyl ester

: ethyl 3-(1′-hydroxy-3′,5′,5′-trimethyl-4′-oxocyclohex-2′-en-1′-yl)propiolate

Conditions

Conditions	Yield
Stage #1: propynoic acid ethyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;	95%

: 24347-58-8
(R,R)-2,3-butandiol

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 917878-27-4
(2R,3R)-2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 24h; Heating;	94%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 536-74-3
phenylacetylene

: 4-hydroxy-2,6,6-trimethyl-4-(phenylethynyl)cyclohex-2-enone

Conditions

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;	94%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 19620-37-2
(+/-)-4-hydroxy-2,6,6-trimethyl-2-cyclohexenone

Conditions

Conditions	Yield
With aluminum isopropoxide In cyclohexane for 5h; Heating;	93.2%
With C29H34BNOP2Ru In dichloromethane; isopropyl alcohol Schlenk technique; Inert atmosphere; Reflux;	84%
With sodium tetrahydroborate; cerium(III) chloride	66%

: 917-92-0
2,2-dimethyl-3-butyne

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 4-(3′,3′-dimethylbut-1′-yn-1′-yl)-4-hydroxy-2,6,6-trimethylcyclohex-2-enone

Conditions

Conditions	Yield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;	93%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 108-24-7
acetic anhydride

: 124743-97-1
4-acetoxy-2,6,6-trimethylcyclohexa-2,4-dienone

Conditions

Conditions	Yield
With 2-(Dimethylamino)pyridine; triethylamine at 48℃; for 17h;	92.6%
With TEA
With dmap; triethylamine

: 3066-71-5
cyclohexyl acrylate

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: (1S,2S,4R)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid cyclohexyl ester

Conditions

Conditions	Yield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -50℃; for 0.333333h; Stage #2: cyclohexyl acrylate In tetrahydrofuran; hexane at -50 - 20℃; for 7h;	92%
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-methylaminopropylated silica gel In tetrahydrofuran; hexane at -70 - 20℃; for 18h; Product distribution; Further Variations:; Reagents; Michael reaction;	90%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 72526-00-2
(-)-8-phenylmenthyl acrylate

A: 946149-26-4
(2S,1R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1S,2S)-1,5,5-trimethyl-6,8-dioxobicyclo[2.2.2]octane-2-carboxylate

B: (2S,1R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 1,5,5-trimethyl-6,8-dioxobicyclo[2.2.2]octane-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: (-)-8-phenylmenthyl acrylate With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -40℃; for 14h; Further stages.;	A 92% B 4%

...Expand

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 922-67-8
propynoic acid methyl ester

: methyl 3-(1′-hydroxy-3′,5′,5′-trimethyl-4′-oxocyclohex-2′-en-1′-yl)propiolate

Conditions

Conditions	Yield
Stage #1: propynoic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;	92%

: 19132-06-0
(2S,3S)-butane-2,3-diol

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 141245-61-6
(2S,3S)-2,3,7,9,9-pentamethyl-1,4-dioxaspiro<4.5>dec-6-en-8-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 4h; Heating;	91%
With toluene-4-sulfonic acid In toluene for 24h; Heating;	91%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 1066-54-2
trimethylsilylacetylene

: 4-hydroxy-2,6,6-trimethyl-4-((trimethylsilyl)ethynyl)cyclohex-2-enone

Conditions

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;	91%

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 221635-90-1
3,3,5-trimethyl-4-oxocyclohexa-1,5-dien-1-yl trifluoromethanesulfonate

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -83℃;	90%
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃; for 2h;	90%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 9.33333h;	88.8%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	88%
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With lithium diisopropyl amide In tetrahydrofuran for 2h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; for 12h; Further stages.;	85%

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 83020-75-1
oxophorone trimethylsilylenol ether

Conditions

Conditions	Yield
With 2,3,5-trimethyl-pyridine In toluene at -40℃;	90%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 292638-85-8
acrylic acid methyl ester

: (1R,2R,4S)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium dibenzylamide In tetrahydrofuran; hexane at -50℃; Stage #2: acrylic acid methyl ester In tetrahydrofuran; hexane at -50 - 20℃;	90%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 38284-11-6
1,3,3-Trimethyl-7-oxabicyclo<4.1.0>heptan-2,5-dion

Conditions

Conditions	Yield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With sodium hydrogencarbonate; sodium carbonate In water at 0 - 25℃; for 1h; Stage #2: With dihydrogen peroxide In water for 3h;	89%
With sodium hydroxide; dihydrogen peroxide In water at 20 - 25℃; for 6h; pH 9-9.5;
Weitz-Scheffer epoxidation; Inert atmosphere;
With quinone oxidoreductase from Fragaria x ananassa, strawberry; NADPH In aq. buffer at 30℃; for 24h; pH=7.5; Reagent/catalyst;
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With sodium hydroxide In water at 0 - 2℃; for 0.166667h; Stage #2: With dihydrogen peroxide In water at 0 - 2℃; for 6h;

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 80-62-6
methacrylic acid methyl ester

: (1S,2S,4R)-1,2,5,5-Tetramethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -50℃; for 0.333333h; Stage #2: methacrylic acid methyl ester In tetrahydrofuran; hexane at -50 - 20℃;	89%
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-methylaminopropylated silica gel In tetrahydrofuran; hexane at -70 - 20℃; Michael reaction;	83%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 513-85-9
2.3-butanediol

: 1402904-89-5
2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; trimethyl orthoformate at 50℃; for 7h; Inert atmosphere;	88%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 69739-34-0
t-butyldimethylsiyl triflate

: 4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohexa-2,4-dienone

Conditions

Conditions	Yield
With 2,3,5-trimethyl-pyridine In toluene at -40℃;	87%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 2-hydroxy-2,6,6-trimethyl-cyclohexane-1,4-dione

Conditions

Conditions	Yield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With phenylsilane; oxygen; isopropyl alcohol; Mn(dpm)3 In 1,2-dichloro-ethane at 0 - 25℃; Stage #2: With triethyl phosphite In 1,2-dichloro-ethane	87%

: 6153-05-5
(Z)-3-methylpent-2-en-4-ynol

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: (Z)-4-hydroxy-4-(5′-hydroxy-3′-methylpent-3′-en-1′-yn-1′-yl)-2,6,6-trimethylcyclohex-2-enone

Conditions

Conditions	Yield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Time; Inert atmosphere; regioselective reaction;	87%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

: 75-36-5
acetyl chloride

: 7479-28-9
2,3,5-trimethyl-1,4-hydroquinone diacetate

Conditions

Conditions	Yield
With 1-methyl-3-(3-triethoxysilanepropyl)imidazolium chloride at 100℃; for 1h;	85.1%

: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

A: 55058-51-0
(4S)-hydroxy-(6R)-2,2,6-trimethylcyclohexanone

B: 60046-49-3
(6R)-levodione

Conditions

Conditions	Yield
With D-glucose; Saccharomyces cerevisiae (baker's yeast, Fermix(R)); oxygen In ethanol for 48h; Product distribution; Kinetics; Further Variations:; conc. of educt and reagents;	A n/a B 85%

2,6,6-Trimethyl-2-cyclohexene-1,4-dione Chemical Properties

Molecular Structure of 2-Cyclohexene-1,4-dione,2,6,6-trimethyl- (CAS NO.1125-21-9):

IUPAC Name: 2,6,6-Trimethylcyclohex-2-ene-1,4-dione
Empirical Formula: C₉H₁₂O₂
EINECS: 214-406-2
Molecular Weight: 152.1904
Surface Tension: 30.8 dyne/cm
Density: 1.02 g/cm³
Flash Point: 84.9 °C
Enthalpy of Vaporization: 45.05 kJ/mol
Boiling Point: 214.2 °C at 760 mmHg
Vapour Pressure: 0.158 mmHg at 25 °C
Index of Refraction: 1.469
Melting Point: 26-28 °C(lit.)
Product Categories: ketone Flavor

2,6,6-Trimethyl-2-cyclohexene-1,4-dione Safety Profile

Hazard Codes: Harmful Xn, Irritant Xi
Risk Statements: 22-43-36/37/38
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3

2,6,6-Trimethyl-2-cyclohexene-1,4-dione Standards and Recommendations

Essence of 2-Cyclohexene-1,4-dione,2,6,6-trimethyl- (CAS NO.1125-21-9) can be used in preparation of ingredients must not exceed the maximum allowable GB 2760 in use and the maximum allowable residue.

2,6,6-Trimethyl-2-cyclohexene-1,4-dione Specification

2-Cyclohexene-1,4-dione,2,6,6-trimethyl- ,with CAS number of 1125-21-9,can be called 2,2,6-trimethyl-2-cyclohexene-1,4-dione (cetoisophorone) ; 2,2,6-trimethylcyclohex-2-en-1,4-dione (4-oxo-isophorone) ; 2,6,6-Trimethy-2-cyclohexene-1,4-dione (4-oxoisophorone) ; 2,6,6-trimethyl-2-cyclohexene-4-dione ; 2,6,6-trimethylcyclohex- ; 2,6,6-trimethylcyclohex-2-ene ; 2-Cyclohexen-1,4-dione, 2,6,6-trimethyl ; 2-Cyclohexene-1,4-dione, 2,6,6-trimethyl- . 2-Cyclohexene-1,4-dione,2,6,6-trimethyl- (CAS NO.1125-21-9) is a clear yellow to orange liquid or low melting solid,can be used for preparation of tobacco flavor and beverage flavors.

Product Name

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

Synthetic route

2,6,6-Trimethyl-2-cyclohexene-1,4-dione Chemical Properties

2,6,6-Trimethyl-2-cyclohexene-1,4-dione Safety Profile

2,6,6-Trimethyl-2-cyclohexene-1,4-dione Standards and Recommendations

2,6,6-Trimethyl-2-cyclohexene-1,4-dione Specification

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