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inquiryProduct Name: Geranylacetone CAS: 3796-70-1 MF: C13H22O MW: 194.31 EINECS: 223-269-8 Product Categories: Mol File: 3796-70-1.mol Geranylacetone Structure Geranylacetone Chemical Properties Boiling point 254-258 °C(lit.)
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inquiryWe are a trading company aiming at providing high-quality services to customers. Established for many years, with good reputation in the industry Storage:Sealed and preserved Application:Fine chemical intermediates, used as the main raw material for
(E)-2-acetyl-5,9-dimethyldeca-4,8-dienoic acid ethyl ester
trans geranyl acetone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 3h; Reflux; | 95% |
With potassium hydroxide In methanol Reflux; | 85% |
Multi-step reaction with 2 steps 1: aq. NaOH / 1.) rt, 2 h; 60 deg C, overnight 2: benzene / 1 h / Heating View Scheme | |
With methanol; potassium hydroxide at 80℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With polystyrene-supported(cathecholato)oxoRe cat. act. by iPrOH; dimethyl sulfoxide In toluene for 4h; Heating; Dean-Stark apparatus; | 93% |
With pyridinium chlorochromate |
(E)-6,10-Dimethyl-3-(toluene-4-sulfonyl)-undeca-5,9-dien-2-one
trans geranyl acetone
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; sodium amalgam In methanol at 0℃; for 2h; | 90% |
(E)-6,10-dimethyl-5,9-undecadien-2-ol
ethylene glycol
A
(5E)-6,10-dimethylundeca-5,9-dien-2-one ethylene acetal
B
trans geranyl acetone
Conditions | Yield |
---|---|
With dimethyl sulfoxide; [ReOCl3(PPh3)2] In toluene for 5h; Heating; | A 82% B 6% |
C25H32S2
trans geranyl acetone
Conditions | Yield |
---|---|
With water; mercury dichloride In acetonitrile for 2h; | 80% |
3-methoxycarbonyl-6,10-dimethyl-E,E-5,9-undecadien-2-one
trans geranyl acetone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 20℃; for 4h; Decarboxylation; | 65% |
Conditions | Yield |
---|---|
Stage #1: trans-geranyl bromide; ethyl acetoacetate With potassium carbonate In acetone at 70℃; Inert atmosphere; Stage #2: With potassium hydroxide In methanol for 3h; Inert atmosphere; Reflux; | 65% |
Conditions | Yield |
---|---|
With sodium diethylmalonate; ethyl-diphenyl-phosphane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 100℃; for 18h; | 50% |
acetoacetic acid-(3,7-dimethyl-octa-2,6-dienyl ester)
trans geranyl acetone
Conditions | Yield |
---|---|
With palladium diacetate; sodium hydride; triphenylphosphine In tert-butyl alcohol at 50℃; for 4h; | 44% |
With palladium diacetate; triphenylphosphine In tert-butyl alcohol at 50℃; for 4h; | 44% |
4-methyleneoxetan-2-one
3,7-dimethylocta-1,6-dien-3-ol
A
(Z)-nerylacetone
B
trans geranyl acetone
geranyl chloride
sodium ethyl acetylacetate enolate
trans geranyl acetone
Conditions | Yield |
---|---|
With ethanol und Erhitzen des Reaktionsprodukts mit wss.-aethanol.Natronlauge; |
geranyl bromide
sodium ethyl acetylacetate enolate
trans geranyl acetone
Conditions | Yield |
---|---|
With ethanol und Erhitzen des Reaktionsprodukts mit wss.-aethanol.Natronlauge; |
3,7-dimethylocta-1,6-dien-3-ol
ethyl acetoacetate
A
(Z)-nerylacetone
B
trans geranyl acetone
Conditions | Yield |
---|---|
With aluminum isopropoxide | |
With aluminum tri-tert-butoxide |
3,7-Dimethylocta-1,6-dien-3-yl acetoacetate
A
(Z)-nerylacetone
B
trans geranyl acetone
Conditions | Yield |
---|---|
With palladium diacetate; sodium hydride; triphenylphosphine In tert-butyl alcohol at 50℃; for 2h; Yield given. Yields of byproduct given; | |
In diphenylether at 190 - 220℃; for 18h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With sulfur dioxide; water at 50℃; for 5h; Yield given; |
Conditions | Yield |
---|---|
With silica gel In benzene for 20h; Heating; dark; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
A
trans geranyl acetone
B
6-Methyl-hept-5-en-2-on
C
(4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal
D
(4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-al
Conditions | Yield |
---|---|
With periodic acid; 3-chloro-benzenecarboperoxoic acid 1.) CH2Cl2, 0 deg C, 30 min, 2.) ether, 15 min; Yield given. Multistep reaction; |
(E)-4-methyl-8-oxo-non-4-enal
isopropyltriphenylphosphonium bromide
trans geranyl acetone
Conditions | Yield |
---|---|
With n-butyllithium 1) THF, hexane, 25 deg C for 1 h, then r.t. 1.5 h, 2) THF, hexane, 25 deg C, 1.5 h, then r.t. 1 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
In tetrachloromethane at 77℃; for 1h; Yields of byproduct given; | |
In benzene for 1h; Heating; Yield given. Yields of byproduct given; | |
In tetrachloromethane at 77℃; for 1h; Yield given. Yields of byproduct given; |
trans geranyl acetone
Conditions | Yield |
---|---|
In benzene for 1h; Heating; Yield given; |
3,7-dimethylocta-1,6-dien-3-ol
2,2-dimethoxy-propane
A
(Z)-nerylacetone
B
trans geranyl acetone
Conditions | Yield |
---|---|
phosphoric acid; acetic acid at 150℃; for 18h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With water; mercury dichloride In acetonitrile for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
4-methyl-4(E)-nonene-1,8-diol
trans geranyl acetone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1)oxalyl chloride, DMSO, 2)triethylamine / 1) CH2Cl2, -60 deg C, 15 min, 2) CH2Cl2, -60 deg C, 5 min, then to r.t. 2: 1) butyllithium / 1) THF, hexane, 25 deg C for 1 h, then r.t. 1.5 h, 2) THF, hexane, 25 deg C, 1.5 h, then r.t. 1 h View Scheme |
bis(trimethylsilyl) ether of 4-methyl-4E-nonene-1,8-diol
trans geranyl acetone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 98 percent / aq. HCl / ethanol / 2 h / Ambient temperature 2: 1)oxalyl chloride, DMSO, 2)triethylamine / 1) CH2Cl2, -60 deg C, 15 min, 2) CH2Cl2, -60 deg C, 5 min, then to r.t. 3: 1) butyllithium / 1) THF, hexane, 25 deg C for 1 h, then r.t. 1.5 h, 2) THF, hexane, 25 deg C, 1.5 h, then r.t. 1 h View Scheme |
diacetate of 4-methyl-4E-nonene-1,8-diol
trans geranyl acetone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 97 percent / NaOH / aq. ethanol / 5 h / Ambient temperature 2: 1)oxalyl chloride, DMSO, 2)triethylamine / 1) CH2Cl2, -60 deg C, 15 min, 2) CH2Cl2, -60 deg C, 5 min, then to r.t. 3: 1) butyllithium / 1) THF, hexane, 25 deg C for 1 h, then r.t. 1.5 h, 2) THF, hexane, 25 deg C, 1.5 h, then r.t. 1 h View Scheme |
linalyl phenylcarbamate
trans geranyl acetone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / Pd2(dba)3*CHCl3; Ph3P / tetrahydrofuran / 12 h / 40 °C 2: 65 percent / KOH / ethanol; H2O / 4 h / 20 °C View Scheme |
3-Carbomethoxy-6,10-dimethyl-5,9-undecadien-2-on
A
trans geranyl acetone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 10percent aq. NaOH / methanol / Ambient temperature 2: benzene / 1 h / Heating View Scheme |
(Z)-3,7-dimethylocta-2,6-dien-1-yl methyl carbonate
A
trans geranyl acetone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) Pd2(dba)3*CHCl3, dppe / 2.) THF, 50 deg C, 3 h 2: 10percent aq. NaOH / methanol / Ambient temperature 3: benzene / 1 h / Heating View Scheme |
geranyl methyl carbonate
A
trans geranyl acetone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) Pd2(dba)3*CHCl3, dppe / 2.) THF, 50 deg C, 3 h 2: 10percent aq. NaOH / methanol / Ambient temperature 3: benzene / 1 h / Heating View Scheme |
trans geranyl acetone
ethylene glycol
(5E)-6,10-dimethylundeca-5,9-dien-2-one ethylene acetal
Conditions | Yield |
---|---|
With pyridine; toluene-4-sulfonic acid In benzene Heating; | 100% |
With toluene-4-sulfonic acid | 93% |
With toluene-4-sulfonic acid |
trans geranyl acetone
4-{3-[2-(3,3-dimethyl-oxiranyl)-ethyl]-3-methyl-oxiranyl}-butan-2-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane | 100% |
With Oxone; Na2B4O7 - Na2(EDTA) buffer; 1,2,4,5-di-O-isopropylidene-D-erythro-2,3-hexodiuro-2,6-pyranose In water; acetonitrile at 0℃; pH=10.5; |
trans geranyl acetone
para-methylphenylmagnesium bromide
E-6,10-dimethyl-2-hydroxy-2-(p-tolyl)-5,9-undecadiene
Conditions | Yield |
---|---|
In diethyl ether at 20℃; | 100% |
trans geranyl acetone
ethyl(diethylphosphono)(fluoro)acetate
cis,trans-2-Fluor-3,7,11-trimethyl-Δ2,6,10-dodecatriensaeureethylester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran | 99% |
trans geranyl acetone
Conditions | Yield |
---|---|
With borane N,N-diethylaniline complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In toluene Product distribution / selectivity; | 99% |
trans geranyl acetone
O-(2,4-dinitrophenyl)hydroxylamine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 20℃; | 99% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0℃; for 0.5h; | 98% |
With lithium aluminium tetrahydride In diethyl ether for 0.166667h; Heating; | 97% |
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.5h; | 96% |
trans geranyl acetone
(4aS,8aS)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-chromene
Conditions | Yield |
---|---|
With class II squalene-hopene cyclase from Alicyclobacillus acidocaldarius variant G600R In aq. acetate buffer at 30℃; for 24h; pH=6; Enzymatic reaction; | 98% |
With squalene–hopene cyclase from Zymomonas mobilis for 20h; Concentration; Reagent/catalyst; Enzymatic reaction; |
trans geranyl acetone
Conditions | Yield |
---|---|
With potassium osmate(VI) dihydrate; methanesulfonamide; C70H63N5O3; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 24℃; for 10h; Reagent/catalyst; Temperature; Sharpless Dihydroxylation; Cooling with ice; enantioselective reaction; | 97% |
With methanesulfonamide; AD-mix-β In water; tert-butyl alcohol at 0℃; for 192h; Sharpless Dihydroxylation; | 7% |
trans geranyl acetone
acetylenemagnesium bromide
dehydronerolidol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; | 96% |
In tetrahydrofuran; dichloromethane for 1h; Ambient temperature; | 90% |
In tetrahydrofuran; diethyl ether at 20℃; for 4h; | 70% |
Stage #1: trans geranyl acetone; acetylenemagnesium bromide In tetrahydrofuran at 23℃; Inert atmosphere; Stage #2: With water In tetrahydrofuran |
trans geranyl acetone
(5E)-9-chloro-6,10-dimethylundeca-5,10-dien-2-one
Conditions | Yield |
---|---|
With N-chloro-succinimide; selenenyl bromide In dichloromethane at 20℃; for 3.5h; | 96% |
With N-chloro-succinimide; Phenylselenyl chloride In dichloromethane at 20℃; for 1.16667h; Inert atmosphere; | 95% |
With sulfuryl dichloride; Cl2CuI; sodium carbonate In various solvent(s) at -5 - 0℃; for 1h; | 172 mg |
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In methanol | 95% |
With hydrogen; [(C6Me6)2Ru2(PPh2)H2][BF4] In ethanol at 60℃; under 37503 Torr; for 24h; | 85% |
With hydrogen; C16AlF36O4(1-)*C32H44IrNO2P(1+) In dichloromethane at 20℃; under 37503.8 Torr; for 2h; Product distribution / selectivity; | 24% |
Conditions | Yield |
---|---|
With potassium 2-methylbutan-2-olate In diethyl ether | 94% |
With potassium hydroxide In diethyl ether | |
With potassium hydroxide |
trans geranyl acetone
[(p-methylphenyl)sulfonylmethyl]isonitrile
(E)-2,6,10-trimethylundeca-5,9-dienenitrile
Conditions | Yield |
---|---|
Stage #1: trans geranyl acetone; [(p-methylphenyl)sulfonylmethyl]isonitrile With potassium tert-butylate In tetrahydrofuran; diethyl ether at 0℃; Inert atmosphere; Stage #2: With ethanol In tetrahydrofuran; diethyl ether at 0 - 20℃; for 4h; Inert atmosphere; | 94% |
With potassium tert-butylate | 94% |
Conditions | Yield |
---|---|
Stage #1: cyclopropyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 2h; Wittig Olefination; Inert atmosphere; Stage #2: trans geranyl acetone In tetrahydrofuran at -2 - 35℃; for 24h; Wittig Olefination; Inert atmosphere; | 93% |
trans geranyl acetone
trimethylsilyl cyanide
(E)-2,6,10-Trimethyl-2-trimethylsilanyloxy-undeca-5,9-dienenitrile
Conditions | Yield |
---|---|
With mercury(II) iodide | 90% |
With zinc(II) iodide In nitromethane |
trans geranyl acetone
(E)-6,10-dimethyl-undeca-5,9-dien-2-one oxime
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride In ethanol for 0.5h; Heating; | 90% |
trans geranyl acetone
carbonic acid dimethyl ester
methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether for 8h; Heating; | 88% |
With sodium hydride In diethyl ether for 2h; Heating; | 82% |
trans geranyl acetone
vinyl magnesium bromide
(E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol
Conditions | Yield |
---|---|
In dichloromethane 1.) 0 deg C, 15 min, 2.) room temperature, 3 h; | 87% |
In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere; | 27% |
With tetrahydrofuran | |
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
trans geranyl acetone
trimethyl orthoformate
(E)-10,10-dimethoxy-2,6-dimethylundeca-2,6-diene
Conditions | Yield |
---|---|
With sulfuric acid In methanol at 65℃; for 3h; | 87% |
With sulfuric acid In methanol at 65℃; for 3h; Inert atmosphere; | 87% |
With sulfuric acid In methanol at 65℃; for 3h; | 87% |
With sulfuric acid In methanol at 5℃; for 3.08333h; Reflux; | 87% |
trans geranyl acetone
(5E)-[1,1,1,3,3-2H5]-6,10-dimethyl-undeca-5,9-dien-2-one
Conditions | Yield |
---|---|
With water-d2; potassium carbonate at 70℃; Inert atmosphere; | 86% |
With water-d2; potassium carbonate at 70℃; Inert atmosphere; | 86% |
With deuteriated sodium hydroxide; deuteromethanol; water-d2 |
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at -30℃; for 19.5h; Inert atmosphere; | 85.7% |
diethoxyphosphoryl-acetic acid ethyl ester
trans geranyl acetone
ethyl farnesoate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Wittig-Horner Reaction; | 85% |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: trans geranyl acetone In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique; | 72% |
With sodium hydride In benzene | 65% |
trans geranyl acetone
benzenesulfinyl-acetonitrile
3,7,11-trimethyl-4-hydroxy-2,6,10-trienenitrile
Conditions | Yield |
---|---|
With piperidine In methanol for 17h; Ambient temperature; | 85% |
trans geranyl acetone
rac-(E)-8-(3,3-dimethyloxiran-2-yl)-6-methyloct-5-en-2-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h; | 85% |
With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; | 71% |
In water at 27℃; for 24h; biotransformation with Mucor griseocyanus DSM 1173, culture-medium: glucose, malt extract, yeast extract, peptone, pH 6.0; | 17.2% |
trans geranyl acetone
[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride
6,10,14-trimethyl-5,9,13-pentadecatriene-2-on
Conditions | Yield |
---|---|
In tert-butyl methyl ether at 0℃; for 6h; Inert atmosphere; | 85% |
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