Conditions | Yield |
---|---|
With sodium acetate; sodium hydroxide In water at 5 - 90℃; Reagent/catalyst; Temperature; | 96.85% |
With barium dihydroxide; water for 2h; Heating; | 82% |
With sodium hydroxide In water at 65℃; Claisen-Schmidt Condensation; | 51% |
With sodium hydroxide for 2.5h; Ambient temperature; Yield given; | |
With hydrotalcite at 59.85℃; Kinetics; Further Variations:; Reagents; |
pseudoionone
Conditions | Yield |
---|---|
Stage #1: Acetic acid (E)-2-(4-methyl-pent-3-enyl)-6-oxo-hept-2-enyl ester With palladium diacetate; triphenylphosphine In 1,4-dioxane at 80℃; for 1h; Elimination; Stage #2: With 1-methyl-pyrrolidin-2-one; iodine at 160℃; for 1h; Isomerization; | 85% |
4-isopropenyl-3,7-dimethyl-1-octyn-6-en-3-ol
A
pseudoionone
B
6,10-dimethyl-3,6,9-undecatrien-2-one
Conditions | Yield |
---|---|
silver nitrate; potassium nitrate In tetrahydrofuran; water for 15h; Heating; | A 12% B 64% |
silver nitrate; potassium nitrate In tetrahydrofuran; water for 15h; Product distribution; Heating; other catalysts in different amounts, different reaction times; | A 12% B 64% |
iodine In various solvent(s) at 165℃; for 4h; Yield given. Yields of byproduct given; | |
hydrogenchloride In various solvent(s) at 165℃; for 1h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
Stage #1: Geraniol With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 1.5h; Stage #2: 1-triphenylphosphoranylidene-2-propanone In dichloromethane at 20℃; for 72h; Wittig reaction; | 57% |
Conditions | Yield |
---|---|
With aluminum isopropoxide; benzene | |
With aluminum tri-tert-butoxide; benzene | |
Multi-step reaction with 2 steps 1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 1.08 h / 0 - 20 °C / Molecular sieve; Inert atmosphere 2: sodium hydroxide / water / 65 °C View Scheme |
acetoacetic acid-(1-ethynyl-1,5-dimethyl-hex-4-enyl ester)
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
at 200℃; | |
With aluminum isopropoxide; acetic acid; decalin at 190℃; |
3,7-dimethyl-octa-1,2,6-trien-1-yl acetate
citral diacetate
acetone
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
With sodium hydroxide |
methoxyethene
(E)-1-iodo-2,6-dimetheylhepta-1,5-diene
(E)-(2-bromoethenyl)diisopropoxyborane
pseudoionone
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
pseudoionone
Conditions | Yield |
---|---|
With sulfur dioxide; water at 50℃; for 96h; Yield given; |
4-isopropenyl-3,7-dimethyl-1-octyn-6-en-3-ol
A
pseudoionone
B
6,10-Dimethyl-2-oxo-3,6,9-undecatriene
C
4-Isopropenyl-7-methyl-3-methylene-oct-6-en-2-one
D
3,5-Diisopropenyl-1-methyl-2-methylene-cyclopentanol
Conditions | Yield |
---|---|
In N,N,N,N,N,N-hexamethylphosphoric triamide at 165℃; for 5h; Yield given. Yields of byproduct given; | |
In various solvent(s) at 165℃; for 5h; Product distribution; also in other solvents, other time; | |
In various solvent(s) at 165℃; for 5h; Yield given. Yields of byproduct given; |
6,10-dimethyl-3,6,9-undecatrien-2-one
pseudoionone
Conditions | Yield |
---|---|
iodine In methanol for 5h; Heating; Yield given; | |
iodine In methanol for 5h; Product distribution; Heating; var. catalysts, solvents, reaction times and temperatures; |
2-methyl-6-methylene-1,3(E),7-octatriene
acetoacetic acid methyl ester
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
C
(5E,8E)-6,10-Dimethyl-undeca-5,8,10-trien-2-one
D
(5E,7E)-6,10-Dimethyl-undeca-5,7,9-trien-2-one
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; | |
Multistep reaction. Yields of byproduct given; |
pseudoionone
Conditions | Yield |
---|---|
With calcium carbonate In toluene for 24h; Heating; Yield given; |
cis-3,7-dimethyl-2,6-octadienal
acetone
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
In sodium hydroxide at 38 - 40℃; for 1.5h; Product distribution; | |
With sodium hydroxide at 38 - 40℃; for 1.5h; Yield given. Yields of byproduct given; |
3,7-dimethyl-2,6-octadienal
acetone
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
In sodium hydroxide at 38 - 40℃; for 1.5h; Product distribution; | |
With sodium hydroxide at 38 - 40℃; for 1.5h; Yield given. Yields of byproduct given; |
7-methyl-3-methylene-6-octenal
acetone
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
With sodium hydroxide at 38 - 40℃; for 1.5h; Yield given. Yields of byproduct given; | |
In sodium hydroxide at 38 - 40℃; for 1.5h; Product distribution; |
(Z)-isocitral
acetone
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
With sodium hydroxide at 38 - 40℃; for 1.5h; Yield given. Yields of byproduct given; | |
In sodium hydroxide at 38 - 40℃; for 1.5h; Product distribution; |
(3E)-3,7-dimethyl-3,6-octadienal
acetone
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
C
(E)-4-Hydroxy-6,10-dimethyl-undeca-6,9-dien-2-one
Conditions | Yield |
---|---|
With sodium hydroxide at 38 - 40℃; for 1.5h; Yield given. Yields of byproduct given; | |
In sodium hydroxide at 38 - 40℃; for 1.5h; Product distribution; |
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
A
pseudoionone
B
(3Z,5E)ψ-ionone
C
5Z-6,10-dimethylundeca-3,5,9-trien-2-one
Conditions | Yield |
---|---|
In methanol for 1h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
With pyridine at 190℃; |
methyllithium
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
With diethyl ether |
6,10-dimethyl-3-phenylthio-5E,9-undecadien-2-one
pseudoionone
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrachloromethane Heating; | |
Multi-step reaction with 2 steps 1: m-chloroperoxybenzoic acid / CH2Cl2 / 3 h / -78 °C 2: 182 mg / NaHCO3 / CCl4 / 5 h / Heating View Scheme |
pseudoionone
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrachloromethane for 5h; Heating; | 182 mg |
acetone
(E/Z)-3,7-dimethyl-2,6-octadienal
A
(3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one
B
pseudoionone
Conditions | Yield |
---|---|
With rehydrated in liquid phase Mg-Al mixed oxide at 59.85℃; for 0.0833333h; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 88 percent / sodium iodide / tetrahydrofuran / 12 h 2.1: NaHCO3 / CCl4 / Heating View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 88 percent / sodium iodide / tetrahydrofuran / 12 h 2.1: m-chloroperoxybenzoic acid / CH2Cl2 / 3 h / -78 °C 3.1: 182 mg / NaHCO3 / CCl4 / 5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0 °C 1.2: tetrahydrofuran 2.1: 182 mg / NaHCO3 / CCl4 / 5 h / Heating View Scheme |
pseudoionone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 60 percent / APTS / acetic acid / 1 h / 70 °C 2.1: Pd(OAc)2; Ph3P / dioxane / 1 h / 80 °C 2.2: 85 percent / iodine; 1-methyl-2-pyrrolidinone / 1 h / 160 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 0 deg C to rt 2: 82 percent / Ba(OH)2, H2O / 2 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / NaH / tetrahydrofuran / 0 deg C, then Rt 1 h 2: 1.) Dibal; 2.) silica gel / 1.) petroleum ether, hexane, -60 deg C, then 10 deg C over 1.5 h; 2.) petroleum ether, hexane, water, -30 deg C, then 0 deg C, 1 h 3: NaOH / 2.5 h / Ambient temperature View Scheme |
5-methyl-4-hexenenitrile
pseudoionone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 70 percent / diethyl ether / 3 h / 0 °C 2: 85 percent / NaH / tetrahydrofuran / 0 deg C, then Rt 1 h 3: 1.) Dibal; 2.) silica gel / 1.) petroleum ether, hexane, -60 deg C, then 10 deg C over 1.5 h; 2.) petroleum ether, hexane, water, -30 deg C, then 0 deg C, 1 h 4: NaOH / 2.5 h / Ambient temperature View Scheme |
pseudoionone
acetylene
(all-E)-3,7,11-Trimethyldodeca-4,6,10-trien-1-yn-3-ol
Conditions | Yield |
---|---|
With lithium methanolate In methanol at 0 - 5℃; for 0.5h; Inert atmosphere; | 98% |
With ammonia; lithium 2) THF, 10 deg C, 5 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogen; nickel In methanol | 95% |
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 |
pseudoionone
ethynylmagnesium chloride
(all-E)-3,7,11-Trimethyldodeca-4,6,10-trien-1-yn-3-ol
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; chloroform-d1; hexane; calcium carbonate | 92% |
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% |
pseudoionone
lithio-6 methyl-3 dimethoxy-1,1 hexadiene-3,5
dimethoxy-1,1 tetramethyl-3,7,11,15 hydroxy-7 hexadecapentaene-3,5,8,10,14
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In diethyl ether at 0℃; for 1.83333h; | 88% |
Conditions | Yield |
---|---|
A n/a B 87% |
Conditions | Yield |
---|---|
With sodium methylsulfinylmethanide In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 1h; | 83% |
pseudoionone
Conditions | Yield |
---|---|
With fluorosulphonic acid; trifluoroacetic acid for 1h; Isomerization; | 75% |
With ω-sulfonic-perfluoroalkylated poly(styrene-maleic anhydride)/silica hybrid nanocomposites In benzene at 80℃; for 1h; | 62% |
pseudoionone
vinyl magnesium bromide
(4E,6E)-3,7,11-trimethyldodeca-1,4,6,10-tetraene-3-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 0.5h; | 71% |
61% |
Conditions | Yield |
---|---|
With sodium hydride In 1,2-dimethoxyethane at 20℃; for 2.5h; | A 65% B n/a C n/a |
6-bromo-3-methyl-1,1-dimethoxy-3,5-hexadiene
pseudoionone
B
(2E,4E,6E,8E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,8,10,14-hexadienal
Conditions | Yield |
---|---|
A 60.8% B n/a |
pseudoionone
ethyltriphenylphosphonium bromide
A
trans(C10)allofarnesene
B
cis(C10)allofarnesene
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.666667h; | A 28% B 32% |
Conditions | Yield |
---|---|
With triethylsilane In dichloromethane at 20℃; for 2h; | A 19% B 23% |
pseudoionone
methyllithium
2,6,10-trimethyl-undeca-2,5,9-triene
Conditions | Yield |
---|---|
(i) Et2O, (ii) Li, NH3; Multistep reaction; |
Conditions | Yield |
---|---|
Multistep reaction; |
pseudoionone
vinyl magnesium bromide
3,7,11-trimethyldodec-1,4,6,10-tetraene-3-ol
pseudoionone
A
(2E,4E,6E)-6,10-dimethyl-undeca-2,4,6,9-tetraene
Conditions | Yield |
---|---|
(i) NaBH4, EtOH, (ii) 4-nitro-benzoyl chloride, Py; Multistep reaction; |
pseudoionone
(3E,5E)-6,10-dimethyl-undeca-3,5,9-trien-2-ol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether | |
With sodium tetrahydroborate In ethanol Ambient temperature; | |
With sodium hydroxide; sodium tetrahydroborate; zinc 2-ethylhexanoate 1.) THF, reflux, 2.) 40 deg, 1 h; Yield given; Multistep reaction; |
pseudoionone
acetic anhydride
(9E)-11-Acetoxy-6,10-dimethyl-3,5,9-undecatrien-2-one
Conditions | Yield |
---|---|
With selenium(IV) oxide |
pseudoionone
propargyl bromide
(5E,7E)-4,8,12-trimethyl-trideca-5,7,11-trien-1-yn-4-ol
Conditions | Yield |
---|---|
(i) Al, HgCl2, THF, (ii) /BRN= 1722925/; Multistep reaction; |
pseudoionone
Dimethyl succinate
11-Apo-ζ-carotin-dicarbonsaeure-(10.11)
Conditions | Yield |
---|---|
(i) KOtBu, (ii) /BRN= 1722925/, (iii) aq. KOH; Multistep reaction; |
IUPAC Name: (3E,5E)-6,10-Dimethylundeca-3,5,9-trien-2-one
Synonyms: Pseudoionone ; Psi-ionone ; 2,6-Dimethylundeca-2,6,8-triene-10-one ; 5,9-Undecatrien-2-one,6,10-dimethyl-3 ; 9-Undecatrien-2-one,6,10-dimethyl-5 ; Pseudoionone,mixtureofisomers ; 2 6-Dimethylhendeca-2 6 8-trien-10-one ; 6,10-Dimethyl-3,5,9-undecatrien-2-one
CAS NO: 141-10-6
Molecular Formula: C13H20O
Molecular Weight: 192.3
Molecular Structure:
EINECS: 205-457-1
Mol File: 141-10-6.mol
Index of Refraction: 1.475
Surface Tension: 28.1 dyne/cm
Density: 0.871 g/cm3
Flash Point: 129 °C
Enthalpy of Vaporization: 53.76 kJ/mol
Boiling Point: 297.8 °C at 760 mmHg
Vapour Pressure: 0.00132 mmHg at 25°C
Appearance: Pseudoionone (CAS NO.141-10-6) is light yellow oily liquid.
Pseudoionone (CAS NO.141-10-6) is used as intermediate of Vitamin A, spice deodorant and perfumer agent.
Citric acid and acetone, treated by bleaching powder, cobalt nitrate, ethanol,can be obtained relatively low purity of Pseudoionone (CAS NO.141-10-6).
Reported in EPA TSCA Inventory.
Slightly toxic by ingestion and skin contact routes. When heated to decomposition it emits acrid smoke and irritating vapors.
Safety Statements 23-24/25
S23:Do not breathe vapour.
S24/25:Avoid contact with skin and eyes.
WGK Germany 2
RTECS YQ2833700
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View