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79-77-6

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79-77-6 Usage

Uses

Different sources of media describe the Uses of 79-77-6 differently. You can refer to the following data:
1. An aroma compound commonly found in essential oils such as rose oil. β-Lonone is an important fragrance chemical used in perfumery. β-Ionone is effective in the chemoprevention of rat mammary carcinogenesis.
2. It is an important fragrance chemical used in perfumery. The combination of α-ionone and β-ionone is characteristic of the scent of violets and used with other components in flavoring to recreate their scent.

Definition

ChEBI: An ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4.

Synthesis Reference(s)

Synthetic Communications, 17, p. 85, 1987 DOI: 10.1080/00397918708063906Tetrahedron Letters, 30, p. 645, 1989 DOI: 10.1016/S0040-4039(01)80271-9

Flammability and Explosibility

Nonflammable

Purification Methods

Convert β-ionone to the semicarbazone (m 149o) by adding 50g of semicarbazide hydrochloride and 44g of potassium acetate in 150mL of water to a solution of 85g of β-ionone in EtOH.

Check Digit Verification of cas no

The CAS Registry Mumber 79-77-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 79-77:
(4*7)+(3*9)+(2*7)+(1*7)=76
76 % 10 = 6
So 79-77-6 is a valid CAS Registry Number.
InChI:InChI=1/C13H20O/c1-10-6-5-7-12(13(10,3)4)9-8-11(2)14/h7-10H,5-6H2,1-4H3/b9-8+/t10-/m1/s1

79-77-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A13400)  beta-Ionone, 96%   

  • 79-77-6

  • 100g

  • 403.0CNY

  • Detail
  • Alfa Aesar

  • (A13400)  beta-Ionone, 96%   

  • 79-77-6

  • 500g

  • 1629.0CNY

  • Detail

79-77-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name β-ionone

1.2 Other means of identification

Product number -
Other names 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:79-77-6 SDS

79-77-6Synthetic route

Conditions
ConditionsYield
With hydrogen fluoride at 0 - 5℃; for 0.333333h; Cyclization;A 98%
B 2%
Conditions
ConditionsYield
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) oxide78%
pseudoionone
141-10-6

pseudoionone

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
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

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

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
With periodic acid In tetrahydrofuran; diethyl ether for 0.1h; Ambient temperature;93%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

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

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

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 0 - 20℃; for 20h;92%
methyllithium
917-54-4

methyllithium

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

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

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0℃; for 1h;89%
Conditions
ConditionsYield
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%
2,6,6-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate
99747-72-5

2,6,6-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate

methyl vinyl ketone
78-94-4

methyl vinyl ketone

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
With bis(triphenylphosphine)palladium(II)-chloride; triethylamine In N,N-dimethyl-formamide at 75℃; for 18h;88%
(3E)-4-(2,6,6-trimethyl-1(2)-cyclohexenyl)-3-buten-2-one-ethylene acetal
14398-32-4

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

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
With lithium chloride In water; dimethyl sulfoxide at 90℃; for 6h;86%
pseudoionone
141-10-6

pseudoionone

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
With sulfuric acid In diethyl ether; acetic acid at 0℃; for 1.5h;85%
With sulfuric acid; acetic acid
N-benzyl-N-methoxy-3-(2,6,6-trimethyl-cyclohex-1-enyl)-acrylamide
884845-78-7

N-benzyl-N-methoxy-3-(2,6,6-trimethyl-cyclohex-1-enyl)-acrylamide

methyllithium
917-54-4

methyllithium

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
In tetrahydrofuran at -78℃;85%
(Z)-4-Hydroxy-6,10-dimethyl-undeca-5,9-dien-2-one
339148-59-3

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

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
With sulfuric acid In hexane at -10℃; for 0.75h;75%
(E)-β-ionone oxime
174390-26-2

(E)-β-ionone oxime

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
With tert.-butylhydroperoxide In tetrachloromethane for 18h; Heating;62%
β-carotene
161023-01-4

β-carotene

A

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

2,2,6-trimethylcyclohexan-1-one

B

(E)-β-ionone
79-77-6

(E)-β-ionone

C

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

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With oxygen In ethyl acetate at 80℃; Catalytic behavior;A n/a
B 62%
C n/a
4-methoxy-β-ionone
122258-61-1

4-methoxy-β-ionone

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at -78℃; for 0.0833333h;60%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

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

1-triphenylphosphoranylidene-2-propanone

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
In dichloromethane at 70℃; under 10500800 Torr; for 5h;59%
5,6-epimino-5,6-dihydro-β-ionone

5,6-epimino-5,6-dihydro-β-ionone

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
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

(E)-β-ionone
79-77-6

(E)-β-ionone

B

5,6-epoxy-trans-β-ionone
36340-49-5

5,6-epoxy-trans-β-ionone

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at -20℃; for 24h;A 43%
B 31%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

acetone
67-64-1

acetone

(E)-β-ionone
79-77-6

(E)-β-ionone

Conditions
ConditionsYield
With potassium hydroxide In water Inert atmosphere; Reflux;40%
With sodium hydroxide In water at 20℃;
Aldol Condensation; Alkaline conditions;
Conditions
ConditionsYield
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
Conditions
ConditionsYield
With aluminum tri-tert-butoxide; acetone
With aluminium(III) phenoxide; acetone
Conditions
ConditionsYield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
13927-47-4

(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A

gamma-ionone
49816-69-5

gamma-ionone

B

(E)-β-ionone
79-77-6

(E)-β-ionone

E

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

(3E,5Z)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

F

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

(3E,5E)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

Conditions
ConditionsYield
With sulfuric acid In toluene at 27 - 38℃; for 1.2h; Product distribution;
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
13927-47-4

(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A

gamma-ionone
49816-69-5

gamma-ionone

B

(E)-β-ionone
79-77-6

(E)-β-ionone

D

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

(3E,5Z)-10-Hydroxy-6,10-dimethyl-undeca-3,5-dien-2-one

Conditions
ConditionsYield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
13927-47-4

(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A

gamma-ionone
49816-69-5

gamma-ionone

B

(E)-β-ionone
79-77-6

(E)-β-ionone

D

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

(3E,5E)-10-Hydroxy-6,10-dimethyl-undeca-3,5-dien-2-one

Conditions
ConditionsYield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
13927-47-4

(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A

gamma-ionone
49816-69-5

gamma-ionone

B

(E)-β-ionone
79-77-6

(E)-β-ionone

D

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

(3E,5Z)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

Conditions
ConditionsYield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
13927-47-4

(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one

A

gamma-ionone
49816-69-5

gamma-ionone

B

(E)-β-ionone
79-77-6

(E)-β-ionone

D

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

(3E,5E)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

Conditions
ConditionsYield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;
Conditions
ConditionsYield
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.
Conditions
ConditionsYield
With sulfuric acid In toluene for 1.2h; Yield given. Further byproducts given;
pseudoionone
141-10-6

pseudoionone

A

gamma-ionone
49816-69-5

gamma-ionone

B

(E)-β-ionone
79-77-6

(E)-β-ionone

E

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

(3E,5Z)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

F

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

(3E,5E)-6,10-Dimethyl-undeca-3,5,10-trien-2-one

Conditions
ConditionsYield
With sulfuric acid In toluene at 27 - 38℃; for 1.2h; Product distribution;
Conditions
ConditionsYield
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 methanol99%
(E)-β-ionone
79-77-6

(E)-β-ionone

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

4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

5,6-epoxy-trans-β-ionone
36340-49-5

5,6-epoxy-trans-β-ionone

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

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

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

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 20h;100%
In tetrahydrofuran for 14h; Ambient temperature;94%
(E)-β-ionone
79-77-6

(E)-β-ionone

trimethylsulfonium methylsulfate
2181-44-4

trimethylsulfonium methylsulfate

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

2-Methyl-2-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]oxirane

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 24h; Ambient temperature;100%
(E)-β-ionone
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

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

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

aqueous sodium chloride

(E)-β-ionone
79-77-6

(E)-β-ionone

trimethylsulphonium iodide
2181-42-2

trimethylsulphonium iodide

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

2-Methyl-2-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]oxirane

Conditions
ConditionsYield
In tetrahydrofuran; water; dimethyl sulfoxide; mineral oil; pentane100%
(E)-β-ionone
79-77-6

(E)-β-ionone

cyanoacetic acid
372-09-8

cyanoacetic acid

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

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

Conditions
ConditionsYield
With piperidine In benzene for 6.5h; Inert atmosphere; Reflux; regioselective reaction;100%
With piperidine In benzene for 18h; Reflux;86%
(E)-β-ionone
79-77-6

(E)-β-ionone

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

(E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

trimethylaluminum
75-24-1

trimethylaluminum

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

4-(2,6,6-trimethyl-cyclohex-1-enyl)-pentan-2-one

Conditions
ConditionsYield
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
(E)-β-ionone
79-77-6

(E)-β-ionone

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

4-(2,2,6-trimethylcyclohexyl)-butan-2-one

Conditions
ConditionsYield
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;
(E)-β-ionone
79-77-6

(E)-β-ionone

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

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

Conditions
ConditionsYield
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%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(E)-β-ionone
79-77-6

(E)-β-ionone

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

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

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

Dimethyl (3-trimethylsilyl-2-propynyl)phosphonate

Dimethyl (3-trimethylsilyl-2-propynyl)phosphonate

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

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

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

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

[13C2]-triethyl phosphonoacetate

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

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

Conditions
ConditionsYield
With sodium hydride In diethyl ether Wittig-Horner reaction;99%
(E)-β-ionone
79-77-6

(E)-β-ionone

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

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

Conditions
ConditionsYield
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
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

(E)-β-ionone
79-77-6

(E)-β-ionone

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

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

Conditions
ConditionsYield
With MgAlCO3-HT In n-heptane for 0.5h; Ambient temperature;98%
(E)-β-ionone
79-77-6

(E)-β-ionone

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

N,N-dimethyl-formamide

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

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

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

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

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

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

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

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

Conditions
ConditionsYield
With cetyltrimethylammonim bromide; sodium hydroxide In water at 20℃; for 24h;97%
With potassium hydroxide In methanol; water at 20℃; for 1.5h;
(E)-β-ionone
79-77-6

(E)-β-ionone

dihydro-α-ionone
98633-46-6

dihydro-α-ionone

Conditions
ConditionsYield
With hydrido(triphenylphosphine)copper(I) hexamer; phenylsilane In toluene for 47h; Ambient temperature;96%
(E)-β-ionone
79-77-6

(E)-β-ionone

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

4-(2,6,6-trimethyl-cyclohex-1-enyl)-butan-2-ol

Conditions
ConditionsYield
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%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

(E)-β-ionone
79-77-6

(E)-β-ionone

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

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

Conditions
ConditionsYield
95%
In diethyl ether
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(E)-β-ionone
79-77-6

(E)-β-ionone

β-ionone
79636-77-4

β-ionone

Conditions
ConditionsYield
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;
(E)-β-ionone
79-77-6

(E)-β-ionone

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

1,2,3,4-tetrahydro-1,1,6-trimethylnaphthalene

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

(7E)-9-ethynyl-β-ionol
17974-59-3

(7E)-9-ethynyl-β-ionol

Conditions
ConditionsYield
95%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

(E)-β-ionone
79-77-6

(E)-β-ionone

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

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

Conditions
ConditionsYield
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%
(E)-β-ionone
79-77-6

(E)-β-ionone

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

N,N-dimethyl-formamide dimethyl acetal

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

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

Conditions
ConditionsYield
for 12h; Heating;95%

79-77-6Relevant articles and documents

PQQ-dependent Dehydrogenase Enables One-pot Bi-enzymatic Enantio-convergent Biocatalytic Amination of Racemic sec-Allylic Alcohols

Gandomkar, Somayyeh,Rocha, Raquel,Sorgenfrei, Frieda A.,Montero, Lía Martínez,Fuchs, Michael,Kroutil, Wolfgang

, p. 1290 - 1293 (2020/12/23)

The asymmetric amination of secondary racemic allylic alcohols bears several challenges like the reactivity of the bi-functional substrate/product as well as of the α,β-unsaturated ketone intermediate in an oxidation-reductive amination sequence. Heading for a biocatalytic amination cascade with a minimal number of enzymes, an oxidation step was implemented relying on a single PQQ-dependent dehydrogenase with low enantioselectivity. This enzyme allowed the oxidation of both enantiomers at the expense of iron(III) as oxidant. The stereoselective amination of the α,β-unsaturated ketone intermediate was achieved with transaminases using 1-phenylethylamine as formal reducing agent as well as nitrogen source. Choosing an appropriate transaminase, either the (R)- or (S)-enantiomer was obtained in optically pure form (>98 % ee). The enantio-convergent amination of the racemic allylic alcohols to one single allylic amine enantiomer was achieved in one pot in a sequential cascade.

Iodine/water-mediated deprotective oxidation of allylic ethers to access α,β-unsaturated ketones and aldehydes

Chen, Weifeng,Jiang, Kezhi,Xue, Yuntian,Yan, Yaolong,Yang, Lei

, p. 14720 - 14724 (2020/04/27)

The first iodine/water-mediated deprotective oxidation of allylic ethers to access α,β-unsaturated ketones and aldehydes was achieved. The reaction tolerates a wide range of functionalities. Furthermore, this protocol was found to be applicable to the oxidative transformation of allylic acetates. The proposed mechanism involves an oxygen transfer from solvent water to the carbonyl products.

An unexpected generation of magnetically separable Se/Fe3O4 for catalytic degradation of polyene contaminants with molecular oxygen

Chen, Xingyu,Mao, Jingfei,Liu, Chuang,Chen, Chao,Cao, Hongen,Yu, Lei

supporting information, p. 3205 - 3208 (2020/08/12)

Selenization of Fe2O3 with NaHSe led to Se/Fe3O4. The unexpected generation of Fe3O4 attributed to the reduction conditions of the reaction, and the resulted magnetic features of the materi

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