methyl vinyl ketone
isoprene
A
5-acetyl-1-methylcyclohexene
B
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With zeolite ZSM-5 In dichloromethane Heating; | A 2% B 98% |
scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; for 13h; | A 6.7% B 91% |
With tin (IV) chloride pentahydrate In benzene at 21℃; for 1h; Inert atmosphere; | A n/a B 10% |
Conditions | Yield |
---|---|
With C36H47AlClN2O(1+)*C24H12BCl8(1-) In dichloromethane at 20℃; for 12h; Reagent/catalyst; Schlenk technique; | 97% |
With tris(pentafluoroethyl)difluorophosphorane In dichloromethane at 0 - 25℃; for 21h; Catalytic behavior; Kinetics; Mechanism; Temperature; Time; Diels-Alder Cycloaddition; | 93% |
With methyltrioxorhenium(VII) In chloroform for 18h; Ambient temperature; | 90% |
1-(4-methyl-3-cyclohexen-1-yl)ethanol
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 2h; | 93% |
A
(Z)-α-bisabolene
B
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 70℃; for 1h; | A 90.7% B n/a |
A
(E)‐α‐bisabolene
B
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 1h; | A 83.3% B n/a |
1-(c-4'-hydroxy-4'-methyl-r-1'-cyclohexyl)ethanone
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With iodine In toluene for 0.25h; Heating; | 81% |
C9H15O(1+)*F6Sb(1-)
A
methyl-4 cyclohexenyl-1 methyle cetone
B
1-(4-methyl-cyclohex-2-enyl)-ethanone
C
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
at 40℃; for 1h; Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 70% |
methyl vinyl ketone
isoprene
A
3-acetyl-1-methylcyclohexene
B
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
at 20℃; for 0.666667h; deposition of a mixture of the substrates on the silica gel; reaction with acroleine; acceleration of a Diels-Alder reaction under adsorption conditions; | A n/a B 70% |
With tin(IV) chloride In benzene at 5 - 10℃; for 2h; |
4-acetyl-1-trimethylsilylmethyl-1-cyclohexene
A
1-(4-Methylenecyclohexyl)ethanone
B
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With potassium fluoride In dimethyl sulfoxide at 120℃; for 12h; | A 10% B 62% |
With potassium fluoride In dimethyl sulfoxide at 120℃; for 12h; Yield given; | |
With potassium fluoride In dimethyl sulfoxide at 120℃; for 12h; Mechanism; Product distribution; Method for preparation of exo-methylenecyclohexanes and cyclohexenes.; |
1-acetyl-2-methyl-2-vinylcyclobutane
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
ethylaluminum dichloride In dichloromethane at 0℃; for 0.5h; | 51% |
α-4-dimethyl-3-cyclohexene-1-acetaldehyde
A
(+-)-4-acetyl-1-methylcyclohexene
B
1-(4-methyl-3-cyclohexen-1-yl)ethanol
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium hydroxide In water; dimethyl sulfoxide; isopropyl alcohol at 20 - 80℃; for 3.5h; | A 12% B 46% |
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With chromium(VI) oxide; sulfuric acid 1-methyl-4-acetyl-cyclohexen-(1) of unknown optical behaviour; |
p-menthane-1,8,9-triol
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With chromium(VI) oxide; sulfuric acid optically inactive 1-methyl-4-acetyl-cyclohexene-(1); |
p-menthane-1,8,9-triol
A
1-(4-hydroxy-4-methylcyclohexyl)ethan-1-one
B
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With sulfate of CrO3 |
1-(4-hydroxy-4-methyl-cyclohexyl)-ethanone semicarbazone
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With oxalic acid isomer(ic) mixture; |
Conditions | Yield |
---|---|
With sulfuric acid; mercury(II) oxide at 45℃; isomer(ic) mixture; |
(R)-2-methyl-2-(4-methylcyclohex-3-en-1-yl)-1,3-dioxolane
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With hydrogenchloride In acetone |
Conditions | Yield |
---|---|
With oxygen; uranyl acetate In pyridine Irradiation; | |
Stage #1: limonene. With cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 In acetonitrile at 55℃; for 0.5h; Stage #2: With dihydrogen peroxide In acetonitrile for 8h; | |
Multi-step reaction with 3 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 2 h / 0 °C / Inert atmosphere 2.1: pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C 3.1: dihydrogen peroxide; potassium hydroxide / dimethyl sulfoxide; isopropyl alcohol; water / 3.5 h / 20 - 80 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 1.2: 2 h / 0 °C / Inert atmosphere 2.1: pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C 3.1: dihydrogen peroxide; potassium hydroxide / dimethyl sulfoxide; isopropyl alcohol; water / 3.5 h / 20 - 80 °C 4.1: pyridinium chlorochromate / dichloromethane / 2 h / 0 - 20 °C View Scheme |
4-oxocyclohexanecarboxylic acid
methyl iodide
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
(i) Li, Et2O, (ii) /BRN= 1635956/; Multistep reaction; |
2-phenylsulfinylmethyl-1,3-butadiene
methyl vinyl ketone
A
5-acetyl-1-methylcyclohexene
B
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
methyl vinyl ketone
isoprene
A
(+-)-4-acetyl-1-methylcyclohexene
B
1-(5-methylcyclohex-3-enyl)ethanone
Conditions | Yield |
---|---|
In toluene at 120℃; for 15h; Yield given; |
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With naphthalene-2-sulfonate at 160 - 180℃; isomer(ic) mixture; |
Conditions | Yield |
---|---|
With diethyl ether isomer(ic) mixture; |
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With chromium(VI) oxide; sulfuric acid 1-methyl-4-acetyl-cyclohexen-(1) of unknown optical behaviour; |
sulfuric acid
p-menthane-1,8,9-triol
A
(+-)-4-acetyl-1-methylcyclohexene
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With acetic acid; zinc |
(4-Methyl-3-pentenyl) diphenylphosphine oxide
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) butyllithium / 1.) hexane, THF, 0 deg C, 30 min; 2.) hexane, THF, -78 deg C; 3.) allowed to warm to r.t. during 2 h 2: sodium hydride / dimethylformamide / 1 h / 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) butyllithium / 1.) hexane, THF, 0 deg C, 30 min; 2.) hexane, THF, -78 deg C; 3.) allowed to warm to r.t. during 2 h 2: 85 percent potassium hydroxide / dimethylsulfoxide / 1 h / 50 °C View Scheme |
trimethyl(2-methylenebut-3-enyl)silane
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 64 percent / aluminium chloride / benzene / 3.5 h / 15 - 20 °C / without cat. at 80 deg C, 36 h 2: KF / dimethylsulfoxide / 12 h / 120 °C View Scheme |
1-acetyl-2-methylcyclobutene
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) CuBr*Me2S / 1) THF, 40 min, -40 deg C or 30 min, -20 deg C 2) 280 min, -40 deg C 2: 51 percent / EtAlCl2 / CH2Cl2 / 0.5 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt Condensation; | 98% |
Conditions | Yield |
---|---|
In diethyl ether for 0.5h; Ambient temperature; | 97% |
With hydrogenchloride 1.) Et2O, 35 deg C, 2 h, 2.) methanol, r.t., 20 min; Yield given. Multistep reaction; |
(+-)-4-acetyl-1-methylcyclohexene
1-(4-methyl-3-cyclohexen-1-yl)ethanol
Conditions | Yield |
---|---|
With aluminium trichloride; diphenylstibane In tetrahydrofuran for 2h; Ambient temperature; | 96% |
With ethanol; sodium | |
With C46H45ClN3O2PRu; sodium hydroxide In isopropyl alcohol at 90℃; for 24h; Reagent/catalyst; Glovebox; |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 2h; Reagent/catalyst; Claisen-Schmidt Condensation; | 96% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 3h; Claisen-Schmidt Condensation; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 2h; Claisen-Schmidt Condensation; | 93% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 3h; Claisen-Schmidt Condensation; | 92% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt Condensation; | 92% |
(+-)-4-acetyl-1-methylcyclohexene
4-acetyl-1,2-epoxy-1-methylcyclohexane
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane Ambient temperature; | 86% |
(+-)-4-acetyl-1-methylcyclohexene
1-(4-methyl-3-cyclohexen-1-yl)-1-ethanone oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In water; acetonitrile at 20℃; for 3h; | 86% |
Conditions | Yield |
---|---|
In diethyl ether for 0.25h; Ambient temperature; | 85% |
With diethyl ether dl-α-terpineol; |
Conditions | Yield |
---|---|
With sodium acetate In water; acetonitrile at 20℃; for 8h; | 82% |
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
With ruthenium trichloride; sodium periodate In ethyl acetate; acetonitrile for 0.05h; | 81% |
Conditions | Yield |
---|---|
With 5 weight% palladium(0) nanoparticles supported on mesoporous natural phosphate In neat (no solvent) for 24h; Reflux; | 80% |
With sulfuric acid |
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide electroreductive coupling; | 80% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt Condensation; | 80% |
(+-)-4-acetyl-1-methylcyclohexene
Conditions | Yield |
---|---|
Stage #1: (+-)-4-acetyl-1-methylcyclohexene With iron(III) chloride In dichloromethane; water at 20℃; Stage #2: With sodium hypochlorite In dichloromethane; water at 20℃; for 0.583333h; | 80% |
Conditions | Yield |
---|---|
With tetraethylammonium tosylate In N,N-dimethyl-formamide electrolytic coupling; | 79% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 2h; Claisen-Schmidt Condensation; | 72% |
(+-)-4-acetyl-1-methylcyclohexene
propargyl magnesium bromide
Conditions | Yield |
---|---|
In diethyl ether for 2h; Ambient temperature; | 70% |
4-methyleneoxetan-2-one
(+-)-4-acetyl-1-methylcyclohexene
6-methyl-2-(4-methylcyclohex-3-en-1-yl)-1,3-dioxin-4-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 20h; Heating; | 70% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 20℃; for 5h; Claisen-Schmidt Condensation; | 68% |
The 4-Acetyl-1-methyl-1-cyclohexene, with the CAS registry number 6090-09-1, is also known as Ethanone, 1-(4-methyl-3-cyclohexen-1-yl)-. It belongs to the classification code of TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]. This chemical's molecular formula is C9H14O and molecular weight is 138.21. What's more, both its IUPAC name and systematic name are the same which is called 1-(4-Methylcyclohex-3-en-1-yl)ethanone.
Physical properties about 4-Acetyl-1-methyl-1-cyclohexene are: (1)ACD/LogP: 2.177; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.18; (4)ACD/LogD (pH 7.4): 2.18; (5)ACD/BCF (pH 5.5): 26.58; (6)ACD/BCF (pH 7.4): 26.58; (7)ACD/KOC (pH 5.5): 364.18; (8)ACD/KOC (pH 7.4): 364.18; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 17.07 Å2; (13)Index of Refraction: 1.465; (14)Molar Refractivity: 41.183 cm3; (15)Molar Volume: 148.982 cm3; (16)Polarizability: 16.326×10-24cm3; (17)Surface Tension: 29.736 dyne/cm; (18)Density: 0.928 g/cm3; (19)Flash Point: 76.667 °C; (20)Enthalpy of Vaporization: 42.571 kJ/mol; (21)Boiling Point: 189.499 °C at 760 mmHg; (22)Vapour Pressure: 0.568 mmHg at 25 °C.
Preparation of 4-Acetyl-1-methyl-1-cyclohexene: this chemical can be prepared by but-3-en-2-one with 2-methyl-buta-1,3-diene. This reaction needs reagent boron trifluoride etherate and solvent CH2Cl2 at temperature of -40 °C. The reaction time is 1 hour. The yield is 84 %.
Uses of 4-Acetyl-1-methyl-1-cyclohexene: it is used to produce other chemicals. For example, it can react with methylmagnesium iodide to get p-menth-1-en-8-ol. The reaction occurs with solvent diethyl ether at ambient temperature. The reaction time is 15 min. The yield is 85 %.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C(C1C/C=C(/C)CC1)C
(2) InChI: InChI=1S/C9H14O/c1-7-3-5-9(6-4-7)8(2)10/h3,9H,4-6H2,1-2H3
(3) InChIKey: HOBBEYSRFFJETF-UHFFFAOYSA-N
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