4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one supplier

Name
4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one
EINECS 201-224-3
CAS No. 79-77-6
Article Data115
CAS DataBase
Density 0.944 g/cm³
Solubility Soluble in water (0.11 mg/mI at 20°C).
Melting Point -49 °C
Formula C₁₃H₂₀O
Boiling Point 254.816 °C at 760 mmHg
Molecular Weight 192.301
Flash Point 121.291 °C
Transport Information UN 3082 9/PG 3
Appearance
Safety 61-36/37-26
Risk Codes 38-51/53-36
Molecular Structure
Hazard Symbols Xi,N
Synonyms 3-Buten-2-one,4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E)- (8CI);(E)-b-Lonone;trans-b-Lonone;
PSA 17.07000
LogP 3.65820

Synthetic route

: 62692-61-9
5E-6,10-dimethylundeca-3,5,9-trien-2-one

A: 79-77-6
(E)-β-ionone

B: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

Conditions

Conditions	Yield
With hydrogen fluoride at 0 - 5℃; for 0.333333h; Cyclization;	A 98% B 2%

: 22029-76-1, 27008-60-2, 35031-11-9, 53078-25-4, 53108-96-6, 81600-95-5, 81801-17-4, 83348-85-0, 472-80-0
beta-ionol

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With sodium hydroxide; dipotassium peroxodisulfate; nickel(II) sulphate In dichloromethane; water for 72h; Ambient temperature;	95%
Stage #1: beta-ionol With 7,7-dichlorocyclohepta-1,3,5-triene In dichloromethane; dimethyl sulfoxide at -30℃; for 0.333333h; Swern Oxidation; Inert atmosphere; Stage #2: With triethylamine In dichloromethane; dimethyl sulfoxide at -30 - 20℃; for 0.333333h; Swern Oxidation; Inert atmosphere;	80%
With ruthenium(IV) oxide	78%

: 141-10-6
pseudoionone

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With C7H13N2O3S(1+)HO4S(1-)Cl0.9Nd0.3 In dichloromethane at 37℃; for 0.75h; Solvent; Temperature; Reagent/catalyst;	94%
With sulfuric acid In nitromethane at 0℃; for 0.25h;	75%
Multi-step reaction with 2 steps 1: 75 percent / CF3CO2H; fluorosulfonic acid / 1 h 2: CF3CO2H; fluorosulfonic acid / 1 h View Scheme

: 2-Methyl-2-[(E)-2-(2,6,6-trimethyl-cyclohex-1-enyl)-vinyl]-[1,3]dithiane

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With periodic acid In tetrahydrofuran; diethyl ether for 0.1h; Ambient temperature;	93%

: 75-16-1
methylmagnesium bromide

: 141208-06-2
(2E)-N-methoxy-N-methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenamide

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
In tetrahydrofuran; toluene at 0 - 20℃; for 20h;	92%

: 917-54-4
methyllithium

: 141208-06-2
(2E)-N-methoxy-N-methyl-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenamide

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0℃; for 1h;	89%

: 141-10-6
pseudoionone

A: 79-77-6
(E)-β-ionone

B: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

Conditions

Conditions	Yield
With sulfuric acid; water In dichloromethane at -20 - 5℃; for 0.916667h; Product distribution / selectivity;	A 88.2% B 0.8%
With sulfuric acid; water In hexane at -20 - 5℃; for 0.916667h; Product distribution / selectivity;	A 88% B 0.6%
With Amberlyst-36 In benzene at 80℃; for 2h;	A 11% B 32%

: 99747-72-5
2,6,6-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate

: 78-94-4
methyl vinyl ketone

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With bis(triphenylphosphine)palladium(II)-chloride; triethylamine In N,N-dimethyl-formamide at 75℃; for 18h;	88%

: 14398-32-4
(3E)-4-(2,6,6-trimethyl-1(2)-cyclohexenyl)-3-buten-2-one-ethylene acetal

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With lithium chloride In water; dimethyl sulfoxide at 90℃; for 6h;	86%

: 141-10-6
pseudoionone

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With sulfuric acid In diethyl ether; acetic acid at 0℃; for 1.5h;	85%
With sulfuric acid; acetic acid

: 884845-78-7
N-benzyl-N-methoxy-3-(2,6,6-trimethyl-cyclohex-1-enyl)-acrylamide

: 917-54-4
methyllithium

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
In tetrahydrofuran at -78℃;	85%

: 339148-59-3
(Z)-4-Hydroxy-6,10-dimethyl-undeca-5,9-dien-2-one

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With sulfuric acid In hexane at -10℃; for 0.75h;	75%

: 174390-26-2
(E)-β-ionone oxime

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In tetrachloromethane for 18h; Heating;	62%

: 161023-01-4
β-carotene

A: 2408-37-9
2,2,6-trimethylcyclohexan-1-one

B: 79-77-6
(E)-β-ionone

C: 432-25-7
2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions

Conditions	Yield
With oxygen In ethyl acetate at 80℃; Catalytic behavior;	A n/a B 62% C n/a

...Expand

: 122258-61-1
4-methoxy-β-ionone

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With trimethylsilyl iodide In dichloromethane at -78℃; for 0.0833333h;	60%

: 432-25-7
2,6,6-trimethylcyclohex-1-enecarbaldehyde

: 1439-36-7
1-triphenylphosphoranylidene-2-propanone

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
In dichloromethane at 70℃; under 10500800 Torr; for 5h;	59%

: 5,6-epimino-5,6-dihydro-β-ionone

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With triethylamine; isopentyl nitrite 1.) 30 min; 2.) CCl4, 80 deg C, 30 min;	43%

tricarbonyl(η4-β-ionone)iron(0): tricarbonyl(η4-β-ionone)iron(0)

A: 79-77-6
(E)-β-ionone

B: 36340-49-5
5,6-epoxy-trans-β-ionone

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In acetone at -20℃; for 24h;	A 43% B 31%

: 432-25-7
2,6,6-trimethylcyclohex-1-enecarbaldehyde

: 67-64-1
acetone

: 79-77-6
(E)-β-ionone

Conditions

Conditions	Yield
With potassium hydroxide In water Inert atmosphere; Reflux;	40%
With sodium hydroxide In water at 20℃;
Aldol Condensation; Alkaline conditions;

: 141-10-6
pseudoionone

A: 79-77-6
(E)-β-ionone

B: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

Conditions

Conditions	Yield
With tungstophosphoric acid on mesoporous SBA-15 In toluene at 109.84℃; under 760.051 Torr; for 6h;
With water; zinc(II) iodide
With water; zinc(II) chloride

: 6627-74-3
(+/-)-α-cyclogeraniol

: 472-20-8
β-cyclogeraniol

A: 79-77-6
(E)-β-ionone

B: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

Conditions

Conditions	Yield
With aluminum tri-tert-butoxide; acetone
With aluminium(III) phenoxide; acetone

...Expand

: 13927-47-4
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A: 49816-69-5
gamma-ionone

B: 79-77-6
(E)-β-ionone

C: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

D: 55955-46-9, 73925-69-6, 84847-78-9, 113084-09-6, 113084-15-4
hydroxyionone

Conditions

Conditions	Yield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;

...Expand

: 13927-47-4
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A: 49816-69-5
gamma-ionone

B: 79-77-6
(E)-β-ionone

C: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

D: 55955-46-9, 73925-69-6, 84847-78-9, 113084-09-6, 113084-15-4
hydroxyionone

E: 33073-35-7
(3E,5Z)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

F: 33073-36-8
(3E,5E)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

Conditions

Conditions	Yield
With sulfuric acid In toluene at 27 - 38℃; for 1.2h; Product distribution;

...Expand

: 13927-47-4
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A: 49816-69-5
gamma-ionone

B: 79-77-6
(E)-β-ionone

C: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

D: 16789-27-8
(3E,5Z)-10-Hydroxy-6,10-dimethyl-undeca-3,5-dien-2-one

Conditions

Conditions	Yield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;

...Expand

: 13927-47-4
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A: 49816-69-5
gamma-ionone

B: 79-77-6
(E)-β-ionone

C: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

D: 16755-27-4
(3E,5E)-10-Hydroxy-6,10-dimethyl-undeca-3,5-dien-2-one

Conditions

Conditions	Yield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;

...Expand

: 13927-47-4
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A: 49816-69-5
gamma-ionone

B: 79-77-6
(E)-β-ionone

C: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

D: 33073-35-7
(3E,5Z)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

Conditions

Conditions	Yield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;

...Expand

: 13927-47-4
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A: 49816-69-5
gamma-ionone

B: 79-77-6
(E)-β-ionone

C: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

D: 33073-36-8
(3E,5E)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

Conditions

Conditions	Yield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;

...Expand

: 13927-47-4
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A: 79-77-6
(E)-β-ionone

B: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

Conditions

Conditions	Yield
With methanol; fluorosulphonic acid In various solvent(s) at -130℃; Product distribution; Other temperatures, other HSO3F-ketone ratios, other SO2ClF-HSO3F ratios, other holding times.;	A 26 % Chromat. B 74 % Chromat.

: 141-10-6
pseudoionone

A: 49816-69-5
gamma-ionone

B: 79-77-6
(E)-β-ionone

C: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

D: 55955-46-9, 73925-69-6, 84847-78-9, 113084-09-6, 113084-15-4
hydroxyionone

Conditions

Conditions	Yield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;

...Expand

: 141-10-6
pseudoionone

A: 49816-69-5
gamma-ionone

B: 79-77-6
(E)-β-ionone

C: 127-41-3, 6901-97-9, 14398-36-8, 24190-29-2, 30685-95-1, 31798-12-6, 52340-45-1, 67529-94-6, 67529-95-7
alpha-ionone

D: 55955-46-9, 73925-69-6, 84847-78-9, 113084-09-6, 113084-15-4
hydroxyionone

E: 33073-35-7
(3E,5Z)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

F: 33073-36-8
(3E,5E)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

Conditions

Conditions	Yield
With sulfuric acid In toluene at 27 - 38℃; for 1.2h; Product distribution;

...Expand

: 79-77-6
(E)-β-ionone

: 22029-76-1, 27008-60-2, 35031-11-9, 53078-25-4, 53108-96-6, 81600-95-5, 81801-17-4, 83348-85-0, 472-80-0
beta-ionol

Conditions

Conditions	Yield
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran for 1.3h; Reduction; Heating;	100%
With sodium tetrahydroborate In methanol at 0 - 20℃;	99%
With sodium tetrahydroborate In methanol	99%

: 79-77-6
(E)-β-ionone

: 17283-81-7
4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on

Conditions

Conditions	Yield
With nickel In tetrahydrofuran at 20℃; for 0.25h; Reduction;	100%
With hydrogen; Wilkinson's catalyst In benzene at 20℃; for 14h; Hydrogenation;	100%
Stage #1: (E)-β-ionone With triethylsilane; Wilkinson's catalyst at 55℃; Reduction; Stage #2: With methanol; potassium carbonate solvolysis;	99%

: 79-77-6
(E)-β-ionone

: 36340-49-5
5,6-epoxy-trans-β-ionone

Conditions

Conditions	Yield
With sodium dodesylsulfate; 3-chloro-benzenecarboperoxoic acid In hexane; water for 24h;	100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 20h; Ambient temperature;	85%
With o-nitrobenzenesulfonyl peroxy radical In acetonitrile at -35℃; for 4h;	85%

: 79-77-6
(E)-β-ionone

: 1826-67-1
vinyl magnesium bromide

: 59057-30-6
(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 20h;	100%
In tetrahydrofuran for 14h; Ambient temperature;	94%

: 79-77-6
(E)-β-ionone

: 2181-44-4
trimethylsulfonium methylsulfate

: 58689-13-7
2-Methyl-2-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]oxirane

Conditions

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 24h; Ambient temperature;	100%

: 79-77-6
(E)-β-ionone

: 2',6',6'-Trimethyl-5-[(E)-2-(2,6,6-trimethyl-cyclohex-1-enyl)-vinyl]-bicyclohexyl-4,1'-dien-3-one

Conditions

Conditions	Yield
With sodium methylate In pentane at 0 - 20℃; Dimerization; Michael addition; Robison annulation;	100%

aqueous sodium chloride: aqueous sodium chloride

: 79-77-6
(E)-β-ionone

: 2181-42-2
trimethylsulphonium iodide

: 58689-13-7
2-Methyl-2-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]oxirane

Conditions

Conditions	Yield
In tetrahydrofuran; water; dimethyl sulfoxide; mineral oil; pentane	100%

...Expand

: 79-77-6
(E)-β-ionone

: 372-09-8
cyanoacetic acid

: 5299-98-9
(2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienenitrile

Conditions

Conditions	Yield
With piperidine In benzene for 6.5h; Inert atmosphere; Reflux; regioselective reaction;	100%
With piperidine In benzene for 18h; Reflux;	86%

: 79-77-6
(E)-β-ionone

: 14393-45-4
(E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid

Conditions

Conditions	Yield
With bromine; sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 6h;	99%
With sodium hydroxide; bromine In 1,4-dioxane; water for 4h; Ambient temperature;	92%
With sodium hypobromide In 1,4-dioxane for 4h; Ambient temperature;	90%

: 79-77-6
(E)-β-ionone

: 75-24-1
trimethylaluminum

: 54344-73-9
4-(2,6,6-trimethyl-cyclohex-1-enyl)-pentan-2-one

Conditions

Conditions	Yield
With copper(I) bromide In tetrahydrofuran; hexane for 2h;	99%
copper(I) bromide In tetrahydrofuran for 0.5h; Ambient temperature;	96%
With bis(acetylacetonate)nickel(II) In diethyl ether

: 79-77-6
(E)-β-ionone

: 52612-51-8, 52612-53-0, 60761-23-1, 64666-26-8, 6138-85-8
4-(2,2,6-trimethylcyclohexyl)-butan-2-one

Conditions

Conditions	Yield
With hydrogen; palladium In diethyl ether at 25℃;	99%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 2h; chemoselective reaction;	98%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 2h; chemoselective reaction;	95%
With hydrogen; β-cyclodextrin/Pd In water at 25℃; under 15001.2 Torr; for 5h;	71%
Hydrogenation;

: 79-77-6
(E)-β-ionone

: 81801-17-4
(2S,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ol

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; bis(1,5-cyclooctadiene)nickel (0); (S)-4-(tert-butyl)-2-(pyrimidin-2-yl)-4,5-dihydrooxazole; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at -25℃; for 0.666667h; Inert atmosphere; Sealed tube; enantioselective reaction;	99%
With (-)-(S)-BINAL-H In tetrahydrofuran 1.) -100 deg C, 1 h; 2.) -78 deg C, 2 h;	87%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 79-77-6
(E)-β-ionone

: 17974-55-9
(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate

Conditions

Conditions	Yield
With sodium hydride In diethyl ether Wittig-Horner reaction;	99%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In diethyl ether at 0 - 20℃; for 2h; Stage #2: (E)-β-ionone In diethyl ether	92.5%
With sodium hydride In tetrahydrofuran at 50℃; for 3h; Emmons-Horner reaction;	70%

: 79-77-6
(E)-β-ionone

: Dimethyl (3-trimethylsilyl-2-propynyl)phosphonate

: trimethyl((5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-enyl)hexa-3,5-dien-1-ynyl)silane

Conditions

Conditions	Yield
Stage #1: Dimethyl (3-trimethylsilyl-2-propynyl)phosphonate With n-butyllithium In tetrahydrofuran at 20℃; Metallation; Stage #2: (E)-β-ionone In tetrahydrofuran Condensation; Horner-Wadsworth-Emmons reaction;	99%

: 79-77-6
(E)-β-ionone

: 100940-60-1
[13C2]-triethyl phosphonoacetate

: 347367-53-7
[10,11-13C2]-(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate

Conditions

Conditions	Yield
With sodium hydride In diethyl ether Wittig-Horner reaction;	99%

: 79-77-6
(E)-β-ionone

: 53163-45-4
[1,1,1-2H3]-(3E)-4-(2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one

Conditions

Conditions	Yield
With deuteromethanol; N-ethyl-N,N-diisopropylamine for 72h;	98%
With [D]-sodium hydroxide In water-d2 at 0 - 25℃; for 12h; Inert atmosphere;	98%
With water-d2; sodium hydride In pyridine at 20℃; for 2h;	93%
With deuteriated sodium hydroxide In 1,4-dioxane; water-d2

: 7677-24-9
trimethylsilyl cyanide

: 79-77-6
(E)-β-ionone

: (E)-2-Methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-2-trimethylsilanyloxy-but-3-enenitrile

Conditions

Conditions	Yield
With MgAlCO3-HT In n-heptane for 0.5h; Ambient temperature;	98%

: 79-77-6
(E)-β-ionone

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 101315-22-4
5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-4-penten-2-yn-1-al

Conditions

Conditions	Yield
Stage #1: (E)-β-ionone With diethyl chlorophosphate; lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: N,N-dimethyl-formamide With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;	97%

: 79-77-6
(E)-β-ionone

: (E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ol

Conditions

Conditions	Yield
Stage #1: (E)-β-ionone With C51H80N4O4; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran at 35℃; for 0.5h; Stage #2: With potassium borohydride In tetrahydrofuran; water at 0℃; for 5h; enantioselective reaction;	97%

: 79-77-6
(E)-β-ionone

: 587-04-2
3-Chlorobenzaldehyde

: 1204518-01-3
(1E,4E)-1-(3-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-1,4-dien-3-one

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 24h;	97%
With potassium hydroxide In methanol; water at 20℃; for 1.5h;

: 79-77-6
(E)-β-ionone

: 98633-46-6
dihydro-α-ionone

Conditions

Conditions	Yield
With hydrido(triphenylphosphine)copper(I) hexamer; phenylsilane In toluene for 47h; Ambient temperature;	96%

: 79-77-6
(E)-β-ionone

: 446293-91-0, 446293-94-3
4-(2,6,6-trimethyl-cyclohex-1-enyl)-butan-2-ol

Conditions

Conditions	Yield
With LaNi5 hydride In tetrahydrofuran; methanol for 33h; Ambient temperature;	95%
With LaNi5 hydride In tetrahydrofuran; methanol 1) 0 deg C, 4 h, 2) r.t., 33 h;	95%
With hydrogen; silica gel; copper; titanium(IV) oxide In isopropyl alcohol at 110℃; under 4560 Torr;	82%

: 917-64-6
methyl magnesium iodide

: 79-77-6
(E)-β-ionone

: 51468-87-2
1.1.3-trimethyl-2-(3-hydroxy-3-methyl-buten-(1)-yl-(1t))-cyclohexene-(2)

Conditions

Conditions	Yield
	95%
In diethyl ether

: 75-77-4
chloro-trimethyl-silane

: 79-77-6
(E)-β-ionone

: 79636-77-4
β-ionone

Conditions

Conditions	Yield
Stage #1: (E)-β-ionone With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 0.5h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -70 - 0℃; for 1.5h;	95%
With lithium diisopropyl amide In tetrahydrofuran
With sodium hydride 1.) hexane, THF, -40 deg C, 15 min, 2.) hexane, THF, from -40 to 0 deg C; Yield given. Multistep reaction;
Stage #1: (E)-β-ionone With potassium hexamethylsilazane In tetrahydrofuran at -75℃; for 0.75h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -75 - 0℃;
With triethylamine; sodium iodide In acetonitrile at 0 - 20℃; for 1h; Inert atmosphere;

: 79-77-6
(E)-β-ionone

: 475-03-6
1,2,3,4-tetrahydro-1,1,6-trimethylnaphthalene

Conditions

Conditions	Yield
toluene-4-sulfonic acid In benzene for 8h; Heating; or with iodine in refluxing CCl4 (15 min);	95%
With iodine In neat (no solvent) at 110℃; for 0.5h;	95%
With iodine at 110℃; Cyclization;	95%

: 79-77-6
(E)-β-ionone

: 4301-14-8
acetylenemagnesium bromide

: 17974-59-3
(7E)-9-ethynyl-β-ionol

Conditions

Conditions	Yield
	95%

: 109-72-8, 29786-93-4
n-butyllithium

: 79-77-6
(E)-β-ionone

: (E)-3-methyl-1-(2,6,6-trimethylcyclohex-1-enyl)-hept-1-en-3-ol

Conditions

Conditions	Yield
Stage #1: n-butyllithium With mischmetall trichloride In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: (E)-β-ionone In tetrahydrofuran; hexane at -78℃; for 3h; Imamoto reaction;	95%

: 79-77-6
(E)-β-ionone

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 866561-15-1
(1E,4E)-1-Dimethylamino-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-1,4-dien-3-one

Conditions

Conditions	Yield
for 12h; Heating;	95%

4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one Consensus Reports

Reported in EPA TSCA Inventory.

4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one Specification

The 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one, with the CAS registry number 79-77-6, is also known as (3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one. It belongs to the product categories of Anti-Proliferative Agents; Antitumor Agents; Carthamus Tinctorius (Safflower Oil); Ephedra Sinica; Aspalathus Linearis (Rooibos Tea); Building Blocks; C13 to C14; Cancer Research; Carbonyl Compounds; Chemical Synthesis; Ginkgo Biloba; Ketones; Nutrition Research; Ocimum Basilicum (Basil); Organic Building Blocks; Phytochemicals by Plant (Food/Spice/Herb); Zingiber Officinale (Ginger). Its EINECS registry number is 201-224-3. This chemical's molecular formula is C₁₃H₂₀O and molecular weight is 192.30. What's more, its IUPAC name is called (E)-4-(2,6,6-Trimethylcyclohexen-1-yl)but-3-en-2-one.

Physical properties about 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one are: (1)ACD/LogP: 3.853; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.85; (4)ACD/LogD (pH 7.4): 3.85; (5)ACD/BCF (pH 5.5): 498.89; (6)ACD/BCF (pH 7.4): 498.89; (7)ACD/KOC (pH 5.5): 2970.55; (8)ACD/KOC (pH 7.4): 2970.55; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.518; (14)Molar Refractivity: 61.704 cm³; (15)Molar Volume: 203.651 cm³; (16)Polarizability: 24.461×10^-24cm³; (17)Surface Tension: 33.617 dyne/cm; (18)Density: 0.944 g/cm³; (19)Flash Point: 121.291 °C; (20)Enthalpy of Vaporization: 49.226 kJ/mol; (21)Boiling Point: 254.816 °C at 760 mmHg; (22)Vapour Pressure: 0.017 mmHg at 25 °C.

Preparation of 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one: this chemical can be prepared by b-Jonol. This reaction needs reagent manganese dioxide and solvent hexane at ambient temperature. The yield is 70 %.

4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one can be prepared by b-Jonol.

Uses of 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one: it is used to produce other chemicals. For example, it can react with (2-isocyano-benzyl)-lithium to get 1-(2-isocyano-phenyl)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-ol. This reaction needs solvent bis-(2-methoxy-ethyl) ether at temperature of -78 °C. The yield is 98 %.

4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one can react with (2-isocyano-benzyl)-lithium to get 1-(2-isocyano-phenyl)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-ol.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes and may present an immediate or delayed danger to one or more components of the environment. And it is irritating to eyes and skin. It is toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. Therefore, you should wear suitable protective clothing, gloves. You should avoid releasing to the environment and refer to special instructions/safety data sheet. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(\C=C\C1=C(\CCCC1(C)C)C)C
(2) InChI: InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+
(3) InChIKey: PSQYTAPXSHCGMF-BQYQJAHWSA-N

Product Name

4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one

Synthetic route

4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one Consensus Reports

4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one Specification

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