2,3-epoxycyclopentanone
cyclopent-2-enone
Conditions | Yield |
---|---|
With Amberlyst 15; sodium iodide In acetone at 20℃; for 3h; deoxygenation; | 96% |
hepta-1,6-dien-3-one
cyclopent-2-enone
Conditions | Yield |
---|---|
With [1,3-bis-mesityl-imidazolidin-2-yl]Cl2(PCp3)Ru=CHCH=CMe2 In dichloromethane for 12h; metathesis; Heating; | 93% |
Conditions | Yield |
---|---|
palladium diacetate In acetonitrile | 93% |
2-hydroxy-2-cyclopenten-1-one
cyclopent-2-enone
Conditions | Yield |
---|---|
93% |
2-bromocyclopentanone
cyclopent-2-enone
Conditions | Yield |
---|---|
With lithium carbonate; hydroquinone; lithium bromide In DMF (N,N-dimethyl-formamide) at 100℃; for 4h; | 91.8% |
Conditions | Yield |
---|---|
With oxygen; palladium matal-containing silica-supported catalyst In various solvent(s) at 59.9℃; for 24h; Product distribution; Mechanism; Pd(0) supported on various zeolites , influence of calcination and reaction temperature and of the solvent; | A 90.1% B n/a |
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h; Product distribution; solvent; | A 90.1% B 0.8% |
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h; Yields of byproduct given; | A 90.1% B n/a |
With oxygen; silica gel; palladium In various solvent(s) at 59.9℃; for 24h; | A 90.1% B 0.8% |
Conditions | Yield |
---|---|
With cerium(III) chloride; sodium iodide In acetonitrile for 0.5h; Ambient temperature; | 90% |
With silica gel; iron(III) chloride at 20℃; for 0.166667h; | 87% |
With ammonium cerium(IV) nitrate In methanol; water at 20℃; for 0.166667h; Ring cleavage; | 86% |
cyclopent-2-enol
cyclopent-2-enone
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(ll) bromide In water; acetonitrile at 20℃; for 3.7h; Inert atmosphere; | 90% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; iron(III) chloride In water; ethyl acetate at 20℃; for 2h; | 78% |
With 4-Phenylpyridine 1-oxide; chloro{bis-N,N'-(salicylaldehyde)ethylenediiminato}chromium(III); iodosylbenzene In dichloromethane at 20℃; for 14h; Oxidation; | 74 % Turnov. |
1-triisopropylsilyl(oxy)-cyclopentene
cyclopent-2-enone
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; disodium hydrogenphosphate; oxygen; palladium dihydroxide In dichloromethane at 24℃; for 42h; | 88% |
Conditions | Yield |
---|---|
With methanesulfonic acid; oxygen; palladium diacetate; molybdovanadophosphate/C In water; acetonitrile at 50℃; for 6h; Wacker-type oxidation; | A 1% B 85% |
With methanesulfonic acid; oxygen; palladium diacetate; molybdovanadophosphate/C In ethanol; water at 50℃; for 6h; Wacker-type oxidation; | A 6% B 75% |
Δ3-dimethyl dihydromuconate
cyclopent-2-enone
Conditions | Yield |
---|---|
With water; Al2O3#dotK2O at 400℃; Industry scale; | 85% |
1,3-epiperoxycyclopentane
A
cyclopent-2-enone
B
4-oxopentanal
C
rac-3-hydroxycyclopentanone
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane Rate constant; Product distribution; Et3N, Dabco, Dabco+AcOH in C6D6; Me4NOAc in CD3Cl; | A n/a B 82% C n/a |
With 1,4-diaza-bicyclo[2.2.2]octane; acetic acid In benzene-d6 0 deg C -> 45 deg C, 65 h; |
3-(tri-n-butyl)stannylcyclopentan-1-one
cyclopent-2-enone
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In water; acetonitrile at 60℃; for 1h; cleavage; | 81% |
(1R,2R,3R)-2,3-Dibromo-cyclopentanol
cyclopent-2-enone
Conditions | Yield |
---|---|
With potassium hydroxide In diethyl ether at 0℃; for 1h; | 80% |
Conditions | Yield |
---|---|
ruthenium trichloride for 48h; Condensation; Heating; | A 8% B 80% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(l) iodide In water; acetonitrile at 45℃; for 0.5h; Reagent/catalyst; Temperature; | 79% |
With pyridine; dmap; 5,10,15,20-tetrakisphenylporphyrin; oxygen; acetic anhydride In dichloromethane for 2h; Irradiation; | 71% |
With tert.-butylhydroperoxide; potassium carbonate; 2.5 mol percent Pd on charcoal In dichloromethane at 0℃; | 71% |
cis- and trans-4-cumyloxy-2-cyclopentenol
A
cyclopent-2-enone
B
isopropenylbenzene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 105℃; | A 76.6% B n/a |
Conditions | Yield |
---|---|
With iodic acid; dimethyl sulfoxide at 45℃; for 6h; | 74% |
With allyl diethyl phosphate; sodium carbonate; palladium diacetate In tetrahydrofuran at 86℃; for 21h; | 63% |
With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 7h; Sealed tube; | 51% |
1-(trimethylsilyl)cyclopentene
A
cyclopent-2-enone
B
2-(trimethylsilyl)-2-cyclopentenyl hydroperoxide
Conditions | Yield |
---|---|
With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane at -10 - -5℃; for 2.5h; Irradiation; Yields of byproduct given; | A n/a B 72% |
5-Chlor-2-cyclopenten-1-on
cyclopent-2-enone
Conditions | Yield |
---|---|
With water; zinc In dimethyl sulfoxide; benzene at 25℃; for 6h; | 71% |
allyl cyclopent-1-en-1-yl carbonate
A
cyclopent-2-enone
B
2-allylcyclopentanone
C
cyclopentanone
Conditions | Yield |
---|---|
palladium diacetate; triphenylphosphine In acetonitrile for 1.5h; Heating; Yields of byproduct given; | A 71% B n/a C n/a |
Conditions | Yield |
---|---|
at 580 - 600℃; | A 70% B n/a |
1-(trimethylsilyloxy)cyclopentene
cyclopent-2-enone
Conditions | Yield |
---|---|
With diallylcarbonate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane In benzonitrile for 1h; Heating; | 69% |
With allyl methyl carbonate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane In acetonitrile Heating; | 81 % Chromat. |
Multi-step reaction with 2 steps 1: 77 percent / CH2Cl2 / 25 °C 2: 1) O3 2) Et2NH / 1) CH2Cl2 / -78 deg C 2) CCl4 / reflux View Scheme | |
With 2,4,6-trimethyl-pyridine; sodium hexafluoroantimonate; Graphite In acetonitrile at 20℃; Electrochemical reaction; Inert atmosphere; | 33 %Chromat. |
Conditions | Yield |
---|---|
With hydrogen In water at 160℃; under 30003 Torr; for 1.2h; Autoclave; | A 31% B 69% |
With water; hydrogen at 160℃; | |
Multi-step reaction with 2 steps 1: hydrogen; sodium carbonate; water / 4 h / 160 °C / 30003 Torr / pH 11 / Autoclave 2: hydrogen; water / 160 °C / Autoclave View Scheme |
Conditions | Yield |
---|---|
With water; zinc at 250℃; for 2.33333h; Autoclave; | A 66.1% B 9.4% |
With water; hydrogen at 160℃; Autoclave; |
C11H12Cl2OSe
cyclopent-2-enone
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water | 64% |
With sodium hydrogencarbonate In dichloromethane for 4h; | 64% |
Conditions | Yield |
---|---|
With hydrogen In water at 150℃; under 15001.5 Torr; Pressure; Reagent/catalyst; Autoclave; Green chemistry; | 61.5% |
With hydrogen In hexane; water at 150℃; for 6h; Reagent/catalyst; Solvent; Temperature; Autoclave; | 52.3% |
Multi-step reaction with 2 steps 1: hydrogen; water / 8 h / 160 °C / Inert atmosphere; Autoclave 2: hydrogen; water / 160 °C / Autoclave View Scheme |
4-methylsulfinyl-4-methylthio-1-cyclopentene
A
cyclopent-2-enone
B
3-Cyclopentenon
Conditions | Yield |
---|---|
With sulfuric acid In water; acetone for 5h; Ambient temperature; | A 6% B 60% |
Conditions | Yield |
---|---|
With [(pentamethylcyclopentadienyl)IrIII(4,4’-dihydroxy-2,2’-bipyridine)(H2O)]SO4; alumina; hydrogen In water at 130℃; under 22502.3 Torr; for 4h; Autoclave; | 60% |
With water; zinc at 250℃; for 2.33333h; Autoclave; | 23.1% |
Multi-step reaction with 2 steps 1: water / 4 h / 160 °C / 750.08 Torr / Inert atmosphere; Autoclave 2: hydrogen; water / 160 °C / Autoclave View Scheme |
cyclopent-2-enone
allyl phenyl sulfoxide
1-(3-oxocyclopentyl)-3-phenylsulfinyl-2-(E)-propene
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane Product distribution; 1.) -78 deg C, 90 min; 2.) -78 deg C, 1.0 h; other temperature, other time; | 100% |
With hydrogenchloride; lithium diisopropyl amide 1.) THF, hexane, -78 to 20 deg C, 1.5 h, then 20 deg C, 30 min; 2.) -78 deg C, 1 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; chloro-trimethyl-silane; lithium iodide In various solvent(s) at -78℃; for 0.1h; | 100% |
cyclopent-2-enone
S-tert-butyl cyanothiolacetate
Cyano-(3-oxo-cyclopentyl)-thioacetic acid S-tert-butyl ester
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; sodium hydride In benzene at 10℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With limonene.; palladium on activated charcoal for 0.5h; Heating; | 100% |
With hydrogen; SC-1 Ni2B In methanol at 25℃; under 760 Torr; for 24h; | 100% |
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 0.5h; Ambient temperature; | 99% |
cyclopent-2-enone
ethyl acetoacetate
ethyl 3-oxo-2-(3-oxocyclopentyl)butanoate
Conditions | Yield |
---|---|
With hydrotalcite at 80℃; for 6h; Michael addition; | 100% |
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 25℃; for 10h; Michael reaction; | 99% |
With zinc trifluoromethanesulfonate at 20℃; for 6h; | 95% |
Conditions | Yield |
---|---|
triethylamine In chloroform for 2h; Ambient temperature; | 100% |
With SBA-15 supported (N-heterocyclic carbene)copper(I) complex In 1,2-dichloro-ethane at 100℃; for 48h; Schlenk technique; Glovebox; Inert atmosphere; stereoselective reaction; | 99% |
With tetra(n-butyl)ammonium hydroxide In ethanol; water at 20℃; for 0.0333333h; Catalytic behavior; Solvent; Michael Addition; Green chemistry; | 99% |
cyclopent-2-enone
diethyl trimethylsilyl phosphite
(3-Trimethylsilanyloxy-cyclopent-2-enyl)-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In acetonitrile at 180℃; for 12h; | 100% |
cyclopent-2-enone
diethyl malonate
3-(bis(ethoxycarbonyl)methyl)cyclopentanone
Conditions | Yield |
---|---|
With hydrotalcite at 80℃; for 6h; Michael addition; | 100% |
With montmorillonite-enwrapped copper at 100℃; for 14h; Michael reaction; | 91% |
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 25℃; for 0.5h; Michael reaction; | 90% |
3-phenyl-propionaldehyde
cyclopent-2-enone
2-(1-hydroxy-3-phenylpropyl)-2-cyclopenten-1-one
Conditions | Yield |
---|---|
With tributylphosphine; 1,1'-bi-2-naphthol In tetrahydrofuran at 20℃; for 1h; Baylis-Hillman addition; | 100% |
With Dimethyl(phenyl)phosphine In methanol; chloroform at 20℃; for 23h; Morita-Baylis-Hillman reaction; | 98% |
With sodium phenoxide; tris[tert-butyl]phosphonium tetrafluoroborate In tetrahydrofuran at 20℃; for 1h; Baylis-Hillman reaction; | 95% |
Conditions | Yield |
---|---|
With tributylphosphine; 1,1'-bi-2-naphthol In tetrahydrofuran at 20℃; for 3h; Baylis-Hillman addition; | 100% |
cyclopent-2-enone
chlorodicyclopentylphosphine
Conditions | Yield |
---|---|
With 4 A molecular sieve; acetic acid at 20℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With chloroform; caesium carbonate; triphenylphosphine; palladium diacetate In toluene at 80℃; for 24h; | 100% |
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; sodium carbonate In water at 80℃; for 1h; | 99% |
With tert-butyl-amphos chloride; sodium dodecyl-sulfate; sodium carbonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene at 20℃; | 99% |
cyclopent-2-enone
Methyl 4,4-dimethyl-3-oxopentanoate
Conditions | Yield |
---|---|
Ru[(S,S)-Msdpen](η6-hexamethylbenzene) In toluene at 30℃; for 24h; Michael reaction; | 100% |
cyclopent-2-enone
4-methoxyphenylboronic acid
(R)-3-(4-methoxyphenyl)cyclopentan-1-one
Conditions | Yield |
---|---|
With potassium hydroxide; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene; bis(ethylene)rhodium(I) chloride dimer In 1,4-dioxane; water at 50℃; for 1h; | 100% |
With chlorobis(ethylene)rhodium(I) dimer; C22H20N2O4; potassium hydroxide In ethanol at 30℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 98% |
With chlorobis(ethylene)rhodium(I) dimer; (R)-6,6'-dimethoxy-P2,P2,P2',P2'-tetrakis-[4-(trifluoromethyl)phenyl]-biphenyl-2,2'-bisphosphine; potassium hydroxide In water; toluene at 20℃; for 6.5h; Inert atmosphere; optical yield given as %ee; stereoselective reaction; | 96% |
cyclopent-2-enone
phenylboronic acid
(R)-3-phenylcyclopentanone
Conditions | Yield |
---|---|
With chlorobis(ethylene)rhodium(I) dimer; (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene; potassium hydroxide In methanol; dichloromethane at 20℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 100% |
With potassium hydroxide; (R,R)-tetrafluorobenzobarrelene rhodium catalyst In 1,4-dioxane at 30℃; for 1h; | 99% |
With chlorobis(ethylene)rhodium(I) dimer; C22H20N2O4; potassium hydroxide In ethanol at 30℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
cyclopent-2-enone
dimethyl (prop-2-yn-1-yl)malonate
2-(3-oxocyclopentyl)-2-prop-2-ynylmalonic acid dimethyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 100% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 100% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 10h; | 70% |
cyclopent-2-enone
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
7-Benzyl-2-oxo-7-azabicyclo[3.3.0]octane
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h; | 100% |
With trifluoroacetic acid In dichloromethane at 20 - 25℃; for 5h; | 81.4% |
With trifluoroacetic acid In dichloromethane at -5 - 0℃; |
cyclopent-2-enone
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
(3aS,6aR)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 18h; | 100% |
With trifluoroacetic acid In dichloromethane at 20℃; for 18h; | 100% |
With trifluoroacetic acid In dichloromethane at 0 - 20℃; Inert atmosphere; | 84% |
cyclopent-2-enone
1-methoxy-N-(3-(trifluoromethyl)benzyl)-N-((trimethylsilyl)methyl)methanamine
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 0.75h; Inert atmosphere; | 100% |
cyclopent-2-enone
3,4-dichlophenylboronic acid
(S)-3-(3,4-dichlorophenyl)cyclopentanone
Conditions | Yield |
---|---|
Stage #1: 3,4-dichlophenylboronic acid With bis(norbornadiene)rhodium(l)tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Stage #2: cyclopent-2-enone With triethylamine In 1,4-dioxane; water at 20℃; for 18h; | 100% |
Stage #1: 3,4-dichlophenylboronic acid With bis(norbornadiene)rhodium(l)tetrafluoroborate; (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Stage #2: cyclopent-2-enone With triethylamine In 1,4-dioxane; water at 20℃; for 18h; | 100% |
cyclopent-2-enone
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine In 1,4-dioxane; water at 20 - 100℃; for 18h; Concentration; Temperature; | 100% |
n-butyl magnesium bromide
chloro-trimethyl-silane
cyclopent-2-enone
((3-butylcyclopent-1-en-1-yl)oxy)trimethylsilane
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide In tetrahydrofuran at -78℃; | 99% |
cyclopent-2-enone
(Z)-ethyl 2-bromobut-2-enoate
2-Oxo-6-vinyl-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.25h; | 99% |
cyclopent-2-enone
dimethyl(phenyl)silyllithium
3-(dimethyl(phenyl)silyl)cyclopentanone
Conditions | Yield |
---|---|
With copper(I) iodide dimethyl sulfide complex In tetrahydrofuran at -78 - 0℃; for 11h; | 99% |
With copper(l) cyanide 1.) THF, 0 deg C, 20 min, 2.) THF, -78 deg C, 2 h; Yield given. Multistep reaction; |
cyclopent-2-enone
2-bromo-2-cyclopenten-1-one
Conditions | Yield |
---|---|
With pyridine N-oxide; N-Bromosuccinimide In acetonitrile at 0 - 20℃; Inert atmosphere; | 99% |
With bromine; triethylamine In dichloromethane | 98% |
Stage #1: cyclopent-2-enone With hydrogen bromide In dichloromethane at -20℃; for 0.0833333h; Inert atmosphere; Stage #2: With bromine In dichloromethane at -24 - -20℃; for 1.5h; Inert atmosphere; Stage #3: With pyridine In dichloromethane at -20 - 0℃; Inert atmosphere; | 97% |
cyclopent-2-enone
2-iodo-cyclopent-2-enone
Conditions | Yield |
---|---|
With dmap; iodine; potassium carbonate In tetrahydrofuran for 1h; | 99% |
With dmap; iodine; potassium carbonate In tetrahydrofuran; water at 25 - 30℃; for 4h; | 99% |
With pyridine; iodine In dichloromethane Ambient temperature; further amines as reagents; | 96% |
Conditions | Yield |
---|---|
With pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane; sodium hydrogencarbonate In tetrahydrofuran; water at 25℃; for 40h; Baylis-Hillman Reaction; | 99% |
With dmap; N,N,N,N,-tetramethylethylenediamine; magnesium iodide In methanol at 20℃; for 5h; Morita-Baylis-Hillman reaction; Inert atmosphere; | 94% |
With 1H-imidazole In tetrahydrofuran; water at 20℃; for 16h; Product distribution; Further Variations:; Solvents; | 92% |
cyclopent-2-enone
diethylzinc
3-ethylcyclopentanone
Conditions | Yield |
---|---|
With 1-[3-((S)-1-hydroxy-3,3-dimethyl-2-butanylamino)-3-oxopropyl]-3-benzylbenzimidazolium iodide; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran; hexane at 20℃; for 3h; | 99% |
Stage #1: diethylzinc With [3-[(1R,2R)-2-(3,5-di-tert-butyl-2-hydroxybenzylamino)cyclohexyl]-1-isopropyl-4-phenyl-3H-imidazol-1-ylidene]copper(I) bromide In diethyl ether at 25℃; for 0.25h; Inert atmosphere; Stage #2: cyclopent-2-enone In diethyl ether at 25℃; for 1.16667h; Inert atmosphere; Stage #3: With hydrogenchloride; water In diethyl ether | 91% |
With copper(I) trifluoromethanesulfonate benzene complex; (+)-3-((tert-butyldimethylsilyl)oxy)-8-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxa-phosphepin-4-yl)-8-azabicyclo[3.2.1]oct-6-ene In hexane; dichloromethane at 0℃; for 12h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere; Schlenk technique; | 68% |
Conditions | Yield |
---|---|
europium-containing poly(2,4-OH2-C6H4COO--co-HCHO)-gel In tetrachloromethane for 10h; Michael addition; Heating; | 99% |
silica gel; ytterbium(III) triflate for 144h; Ambient temperature; | 87% |
With trifluoroacetic acid In acetonitrile at 20℃; for 60h; Addition; Michael addition; | 72% |
cyclopent-2-enone
phenylboronic acid
(S)-3-phenylcyclopentanone
Conditions | Yield |
---|---|
With potassium phosphate; chlorobis(ethylene)rhodium(I) dimer; C25H27NO3S In 1,4-dioxane; water at 60℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Stage #1: phenylboronic acid With chlorobis(ethylene)rhodium(I) dimer; (R)-N-cinnamyl-2-methylpropane-2-sulfinamide In 1,4-dioxane at 40℃; for 0.5h; Inert atmosphere; Stage #2: cyclopent-2-enone With potassium phosphate In 1,4-dioxane; water at 40℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
With chlorobis(ethylene)rhodium(I) dimer; (R)-(+)-[(η5-1-bis(3,5-dimethylphenyl)phosphino-2-(3-diphenylphosphino-2-methylpropenyl)cyclopentadienyl-P)]manganese(I) dicarbonyl; potassium hydroxide In 1,4-dioxane; water at 50℃; for 7h; Inert atmosphere; enantioselective reaction; | 99% |
The 2-2-Cyclopentenone with CAS registry number of 930-30-3 is also known as 2-Cyclopentenone. The IUPAC name is Cyclopent-2-en-1-one. It belongs to product categories of Ring Systems; C3 to C6; Carbonyl Compounds; Ketones. Its EINECS registry number is 213-213-0. In addition, the formula is C5H6O and the molecular weight is 82.10. This chemical is a clear yellow liquid that almost insoluble in water but soluble in alcohol and ether. What's more, it may cause inflammation to the skin or other mucous membranes and may cause damage to health. It should be sealed at the temperature of 4 °C at room temperature away from oxidants.
Physical properties about 2-2-Cyclopentenone are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 20.652; (4)ACD/KOC (pH 7.4): 20.652; (5)#H bond acceptors: 1; (6)Index of Refraction: 1.492; (7)Molar Refractivity: 22.793 cm3; (8)Molar Volume: 78.507 cm3; (9)Surface Tension: 36.818 dyne/cm; (10)Density: 1.046 g/cm3; (11)Flash Point: 40.045 °C; (12)Enthalpy of Vaporization: 37.34 kJ/mol; (13)Boiling Point: 135.999 °C at 760 mmHg; (14)Vapour Pressure: 7.529 mmHg at 25 °C.
Preparation of 2-2-Cyclopentenone: it is prepared by elimination of α-bromo-cyclopentanone using lithium carbonate and claisen condensation-decarboxylation-isomerization cascades of unsaturated diesters.
Uses of 2-2-Cyclopentenone: it is used to produce 1-deuterio-2-cyclopentenol. The reaction occurs with reagent LiAlD4 and solvent diethyl ether with other condition of heating for 15 minutes. The yield is about 84%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It also is flammable and harmful if swallowed. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1CC(=O)C=C1
2. InChI: InChI=1S/C5H6O/c6-5-3-1-2-4-5/h1,3H,2,4H2
3. InChIKey: BZKFMUIJRXWWQK-UHFFFAOYSA-N
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