1-(trimethylsilyloxy)cyclopentene
methyl iodide
A
2-Methylcyclopentanone
B
2,2-dimethylcyclopentanone
C
cis-2,5-dimethylcyclopentanone
(+/-)-trans-2,5-dimethylcyclopentanone
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium; dimethyl zinc(II) In tetrahydrofuran at -78℃; for 10h; | A 98% B n/a C n/a D n/a |
With methyllithium In tetrahydrofuran at 0℃; for 3h; Further byproducts given; | A 79% B n/a C n/a D n/a |
5,5-dimethylcyclopent-2-enone
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol for 6h; Ambient temperature; | 96% |
With lithium tri(t-butoxy)aluminum hydride In tetrahydrofuran at -78℃; for 2h; | 66% |
1-(2-hydroxyprop-2-yl)cyclobutanol
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Rearrangement; | 93% |
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With acetic acid; zinc at 110℃; for 2h; | 92% |
5-iodo-2,2-dimethylpentanenitrile
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
Stage #1: 5-iodo-2,2-dimethylpentanenitrile With n-hexyllithium In tetrahydrofuran; hexane at -20 - -5℃; for 1.33333h; Stage #2: With oxalic acid In tetrahydrofuran; hexane; water at -5 - 20℃; | 81% |
With magnesium; ethylene dibromide In diethyl ether |
1-(trimethylsilyloxy)cyclopentene
methyl iodide
A
2-Methylcyclopentanone
B
2,2-dimethylcyclopentanone
C
2,2,5-trimethylcyclopentanone
D
cis-2,5-dimethylcyclopentanone
Conditions | Yield |
---|---|
With methyllithium In tetrahydrofuran at 0℃; for 3h; Further byproducts given; | A 79% B n/a C n/a D n/a |
With methyllithium 1.) THF, 2.) 0 deg C, 3 h; Multistep reaction. Further byproducts given. Yields of byproduct given; |
1-(trimethylsilyloxy)cyclopentene
methyl iodide
A
2-Methylcyclopentanone
B
2,2-dimethylcyclopentanone
C
2,2,5-trimethylcyclopentanone
D
cis-2,5-dimethylcyclopentanone
(+/-)-trans-2,5-dimethylcyclopentanone
Conditions | Yield |
---|---|
With methyllithium In tetrahydrofuran at 0℃; for 3h; Product distribution; var. temp., times, and reagent systems; other lithium enolates; | A 79% B n/a C n/a D n/a E n/a |
trans-1,2-dimethylcyclopentan-1,2-diol
1-(2-hydroxyprop-2-yl)cyclobutanol
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With phosphoric acid; phosphorus pentoxide at 45℃; for 0.166667h; Rearrangement; | 66% |
1-(1-Methyl-1-methylselanyl-ethyl)-cyclobutanol
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With potassium hydroxide; chloroform; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 20℃; for 1h; | 63% |
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
bei langsamer Destillation; |
Conditions | Yield |
---|---|
With diethyl ether; sodium amide anschliessend Behandeln mit Methyljodid, zuletzt auf dem Dampfbad; |
Conditions | Yield |
---|---|
With thorium hydroxide at 280 - 290℃; | |
With barium dihydroxide at 285℃; |
cis-1,2-dimethyl-1,2-cyclopentanediol
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With sulfuric acid | |
With D3+; oxygen; trimethylamine at 37.5℃; Product distribution; Irradiation; trans compound and various conditions investigated; |
rac-2,2-dimethylcyclopentanol
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With potassium permanganate at 20℃; Erwaermen des Reaktionsprodukts auf 50grad; | |
With chromium(VI) oxide; sulfuric acid In acetone |
Conditions | Yield |
---|---|
With sodium tert-pentoxide; dimethyl sulfate | |
In carbonic acid dimethyl ester |
2-Methylcyclopentanone
methyl iodide
A
2,2-dimethylcyclopentanone
B
2,5-dimethylcyclopentanone
Conditions | Yield |
---|---|
With sodium amide |
Conditions | Yield |
---|---|
With hydrogenchloride; mercury; zinc | |
With titanium tetrachloride; lithium trimethylstannyl 1.) THF, 0 deg C, 15 min, 2.) CH2Cl2, -78 deg C, 15 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
(i) NaNH2, Et2O, (ii) H2SO4, AcOH; Multistep reaction; |
Conditions | Yield |
---|---|
With sodium tert-pentoxide In diethyl ether; benzene | |
With sodium tert-pentoxide In toluene at 20 - 35℃; for 28h; | 5.2 g |
2-<(n-butylthio)methylene>cyclopentanone
methyl iodide
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
(i) Li, liq. NH3, H2O, Et2O, (ii) /BRN= 969135/; Multistep reaction; |
Conditions | Yield |
---|---|
(PPh3)2Co(dppe) In acetonitrile; benzene at 70℃; for 3h; Yield given; |
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine 1.) hexane, THF, -78 deg C, 0.5 h, then 0 deg C, 3 h 2.) 3 h; Yield given. Multistep reaction; |
2-Methylcyclopentanone
methyl iodide
A
2,2-dimethylcyclopentanone
B
2,5-dimethylcyclopentanone
C
2,2,5-trimethylcyclopentanone
D
2,2,5,5-tetramethylcyclopentanone
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
2-Methylcyclopentanone
methyl iodide
A
2,2-dimethylcyclopentanone
B
2,5-dimethylcyclopentanone
C
2,4-dimethylcyclopentanone
Conditions | Yield |
---|---|
With (2-pyrr)2Mg electrogenerated base In N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane at -50℃; for 1.5h; Product distribution; other temperatures, time, recyclization; |
2-Methylcyclopentanone
methyl iodide
A
2,2-dimethylcyclopentanone
B
2,5-dimethylcyclopentanone
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With acetic anhydride |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water for 5h; Baeyer-Villiger Ketone Oxidation; Reflux; | 100% |
With trifluoroacetyl peroxide at 0℃; | 99% |
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h; Baeyer-Villiger Ketone Oxidation; | 77% |
With dihydrogen peroxide; trifluoroacetic anhydride at 20℃; Baeyer-Villiger oxidation; | 67% |
With Mg10Al2(OH)24CO3; oxygen; benzaldehyde In 1,2-dichloro-ethane at 40℃; for 24h; | 61% |
2,2-dimethylcyclopentanone
(R)-1-phenyl-ethyl-amine
(R,E)-N-(2,2-dimethylcyclopentylidene)-1-phenylethanamine
Conditions | Yield |
---|---|
With titanium tetrachloride; triethylamine In dichloromethane at 20℃; for 16h; Cooling with ice; | 100% |
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With sodium acetate In methanol Reflux; | 100% |
2,2-dimethylcyclopentanone
ketene t-butyldimethylsilyl methyl acetal
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylcyclopentanone With bis(trifluoromethanesulfonyl)amide In diethyl ether at -78 - 23℃; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere; Stage #2: ketene t-butyldimethylsilyl methyl acetal In diethyl ether at -20℃; for 0.5h; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In toluene at 100℃; for 22h; | 97% |
In toluene at 100℃; for 22h; Temperature; | 97% |
trimethylsilyl cyanide
2,2-dimethylcyclopentanone
2,2-Dimethyl-1-trimethylsilanyloxy-cyclopentanecarbonitrile
Conditions | Yield |
---|---|
With zinc(II) iodide In benzene for 7.5h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
at 20 - 110℃; for 2.75h; Inert atmosphere; | 95% |
at 110℃; for 1h; Inert atmosphere; | 94% |
2,2-dimethylcyclopentanone
2-Trifluoromethylbenzaldehyde
5-[1-(2-trifluoromethylphenyl)-meth-(E)-ylidene]-2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 0 - 20℃; | 94% |
N,N-phenylbistrifluoromethane-sulfonimide
2,2-dimethylcyclopentanone
5,5-dimethylcyclopent-1-en-1-yl trifluoromethanesulfonate
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylcyclopentanone With lithium diisopropyl amide In tetrahydrofuran; n-heptane at -78℃; for 1h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃; for 1h; | 92% |
Stage #1: 2,2-dimethylcyclopentanone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran; hexane at -78 - 20℃; for 3h; | 50% |
Stage #1: 2,2-dimethylcyclopentanone With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 3h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃; for 1h; | 28% |
2,2-dimethylcyclopentanone
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 2,2-dimethylcyclopentanone In dichloromethane at 20 - 40℃; for 17h; Inert atmosphere; | 91.93% |
2,2-dimethylcyclopentanone
malononitrile
cyano (2,2-dimethylcyclopentylidene) acetonitrile
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid In toluene Heating / reflux; | 91% |
With piperidine; benzoic acid In benzene for 100h; Condensation; Heating; | 61% |
2,2-dimethylcyclopentanone
oxalic acid diethyl ester
ethyl 2-(3,3-dimethyl-2-oxo-cyclopentyl)-2-oxo-acetate
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylcyclopentanone; oxalic acid diethyl ester With ethanol; sodium ethanolate; sodium hydride at 0 - 20℃; for 6.25h; Stage #2: With hydrogenchloride In ethanol; water at 0℃; | 90% |
With sodium ethanolate | |
In ethanol | |
With sodium ethanolate In ethanol at -15 - 20℃; Inert atmosphere; | 8.2 g |
With sodium ethanolate In ethanol at -15 - 20℃; Inert atmosphere; | 8.2 g |
2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylcyclopentanone With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; pentane at 0℃; for 0.25h; Aldol Condensation; Inert atmosphere; Stage #2: 1-(2-hydroxy-1-((4-methoxybenzyl)oxy)propan-2-yl)cyclopropane-1-carbaldehyde In tetrahydrofuran; N,N-dimethyl-formamide; pentane at 0℃; for 0.25h; Inert atmosphere; | 90% |
2,2-dimethylcyclopentanone
2,4-difluorobenzaldehyde
5-[1-(2,4-difluorophenyl)-meth-(E)-ylidene]-2,2-dimethylcyclopentanone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 0 - 20℃; | 88% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil for 24h; Reflux; | 88% |
With sodium hydride |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0) In methanol at 80℃; for 18h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube; | 87% |
2,2-dimethylcyclopentanone
rac-2,2-dimethylcyclopentanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 20℃; for 3h; | 86% |
With borane-THF; L-proline In tetrahydrofuran for 0.166667h; Reduction; | 78% |
With sodium tetrahydroborate In isopropyl alcohol at 25℃; for 20h; Kinetics; |
2,2-dimethylcyclopentanone
2-Iodobenzyl bromide
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylcyclopentanone With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 2-Iodobenzyl bromide In tetrahydrofuran; hexane at -78 - 0℃; for 1.5h; Schlenk technique; Inert atmosphere; | 85% |
2,2-dimethylcyclopentanone
benzaldehyde
(E)-2-benzylidene-5,5-dimethylcyclopentanone
Conditions | Yield |
---|---|
With sodium methylate In methanol for 16h; Ambient temperature; | 84% |
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-2H-furan With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - 0℃; for 1h; Stage #2: 2,2-dimethylcyclopentanone In tetrahydrofuran; pentane at -78 - 20℃; for 6h; Stage #3: With Dowex-50X In dichloromethane at 20℃; for 24h; Further stages.; | 81% |
2,2-dimethylcyclopentanone
(R)-2,2-dimethylcyclopentan-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran for 1h; in air; | 80% |
Stage #1: 2,2-dimethylcyclopentanone With (4R,5R)-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylic acid In tetrahydrofuran for 0.25h; Cooling with ice; Stage #2: With sodium tetrahydroborate In tetrahydrofuran for 2h; optical yield given as %ee; | 80% |
With (+)-diiso-2-ethylapophosphate pinacylboraneheptane In ethyl acetate at -25℃; for 24h; | 68% |
With diisopinocamphenylchloroborane Yield given; | |
With Octanethiol; 2,4-dinitrobenzenesulfonic acid; (2S,4S)-pentane-2,4-diol In benzene for 1.5h; Reflux; optical yield given as %ee; | 36 %Spectr. |
2,2-dimethylcyclopentanone
carbonic acid dimethyl ester
methyl 3,3-dimethyl-2-oxocyclopentyl-1-carboxylate
Conditions | Yield |
---|---|
With sodium hydride In methanol at 82℃; for 5h; | 79.5% |
Conditions | Yield |
---|---|
With pyridine at 20℃; for 18h; Inert atmosphere; | 79% |
The 2,2-Dimethylcyclopentanone, with the CAS registry number 4541-32-6, is also known as Cyclopentanone, 2,2-dimethyl-. It belongs to the product categories of C7 to C8; Carbonyl Compounds; Ketones. This chemical's molecular formula is C7H12O and formula weight is 112.17. What's more, its IUPAC name is called 2,2-dimethylcyclopentan-1-one. This chemical is clear colorless to yellow liquid.
Physical properties of 2,2-Dimethylcyclopentanone: (1)ACD/LogP: 1.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.23; (4)ACD/LogD (pH 7.4): 1.23; (5)ACD/BCF (pH 5.5): 5.07; (6)ACD/BCF (pH 7.4): 5.07; (7)ACD/KOC (pH 5.5): 111.31; (8)ACD/KOC (pH 7.4): 111.31; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.438; (13)Molar Refractivity: 32.51 cm3; (14)Molar Volume: 123.6 cm3; (15)Surface Tension: 27.1 dyne/cm; (16)Density: 0.907 g/cm3; (17)Flash Point: 32.8 °C; (18)Enthalpy of Vaporization: 38.51 kJ/mol; (19)Boiling Point: 148.1 °C at 760 mmHg; (20)Vapour Pressure: 4.29 mmHg at 25°C.
Preparation: this chemical can be prepared by 5,5-dimethyl-cyclopent-2-enone. This reaction will need reagent lithium tri-t-butoxyaluminium hydride and solvent tetrahydrofuran. The reaction time is 2 hours with reaction temperature of -78 ℃. The yield is about 66%.
Uses of 2,2-Dimethylcyclopentanone: it can be used to produce 5,5-dimethyl-1-morpholinocyclopentene. This reaction will need reagent p-toluenesulfonic acid and solvent toluene with reaction time of 36 hours. The yield is about 75%.
When you are using this chemical, please be cautious about it as the following:
This chemical is flammable. You should keep it away from sources of ignition - No smoking. In addition, please do not empty into drains. Besides, you should take precautionary measures against static discharges.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1(CCCC1=O)C
(2)InChI: InChI=1S/C7H12O/c1-7(2)5-3-4-6(7)8/h3-5H2,1-2H3
(3)InChIKey: FTGZMZBYOHMEPS-UHFFFAOYSA-N
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