Ethyl 2-oxocyclopentanecarboxylate supplier

Name
Ethyl 2-oxocyclopentanecarboxylate
EINECS 210-253-0
CAS No. 611-10-9
Article Data89
CAS DataBase
Density 1.12 g/cm³
Solubility insoluble in water
Melting Point
Formula C₈H₁₂O₃
Boiling Point 228.2 °C at 760 mmHg
Molecular Weight 156.181
Flash Point 77.8 °C
Transport Information
Appearance clear colourless to pale yellow liquid
Safety 23-24/25-36/37-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1-Oxocyclopentane-2-carboxylic acid ethyl ester;2-(Ethoxycarbonyl)-1-cyclopentanone;2-(Ethoxycarbonyl)cyclopentanone;2-Carbethoxy-1-cyclopentanone;2-Carbethoxycyclopentanone;2-Cyclopentanonecarboxylic acid ethyl ester;2-Oxocyclopentanecarboxylic acidethyl ester;Ethyl 1-oxocyclopentane-2-carboxylate;Ethyl 2-cyclopentanone-1-carboxylate;Ethyl 2-cyclopentanonecarboxylate;Ethyl2-oxocyclopentanoate;NSC 22055;NSC 5658;a-(Carboethoxy)cyclopentanone;
PSA 43.37000
LogP 0.91870

Synthetic route

: 141-28-6
diethyl adipate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With sodium methylate at 150℃;	100%
With sodium ethanolate at 120℃; under 7.50075 Torr; for 0.75h;	99%
With potassium tert-butylate In toluene for 3h; Heating;	98%

: oxime of ethyl cyclopentanone-2-carboxylate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With (Bu4N)2S2O8 In 1,2-dichloro-ethane for 1.5h; Heating;	94.3%

: 64-17-5
ethanol

: 10472-24-9
methyl 2-oxocyclopentane-1-carboxylate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 24h; Heating;	92%

: ethyl 2-(methyloxyimino)-1-cyclopentanecarboxylate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With formaldehyd; Amberlyst 15 In water; acetone at 110℃; for 13h;	90%

: 16689-52-4
2-semicarbazono-cyclopentanecarboxylic acid ethyl ester

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 80℃; for 1h; oxidative cleavage;	88%

: 300674-80-0
2-benzyloxyimino-cyclopentanecarboxylic acid ethyl ester

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetone Hydrolysis;	85%

: 23153-73-3
ethyl 1,4-dioxaspiro[4,4]nonane-6-carboxylate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
indium(III) chloride In methanol; water for 1.41667h; Heating;	84%

: 78647-27-5
S-ethyl O-ethyl adipic acid diester

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -30℃; for 3h;	74%

: 626-86-8
adipinic acid monoethyl ester

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With aluminium trichloride; triethylamine In dichloromethane Dieckmann cyclization;	71%
at 270 - 280℃; bei der thermischen Zersetzung;

: ethyl 1-iodo-2-oxocyclopentanecarboxylate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 125℃; under 2585.74 Torr; for 0.025h; microwave irradiation;	70%

: 42593-11-3
ethyl 1-bromo-2-oxocyclopentanecarboxylate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With water; 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate at 125℃; under 2585.74 Torr; for 0.0333333h; microwave irradiation;	70%

: 120-92-3
cyclopentanone

: 1609-47-8
diethyl dicarbonate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With potassium hydride In benzene for 0.5h; Heating;	61%

: 141-28-6
diethyl adipate

: 125541-06-2
potassium 2,4-dimethyl-1-naphthoxide

A: 125541-07-3
2-Hydroxy-2,7a-dimethyl-1a,7a-dihydro-2H-1-oxa-cyclopropa[b]naphthalen-7-one

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With 18-crown-6 ether; oxygen In tetrahydrofuran for 3h; Mechanism; Product distribution; Ambient temperature;	A 60% B 35%

...Expand

: 141-28-6
diethyl adipate

A: 125541-07-3
2-Hydroxy-2,7a-dimethyl-1a,7a-dihydro-2H-1-oxa-cyclopropa[b]naphthalen-7-one

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium 2,4-dimethyl-1-naphthoxide; oxygen In tetrahydrofuran for 3h; Ambient temperature;	A 60% B 35%

: 125541-06-2
potassium 2,4-dimethyl-1-naphthoxide

A: 125541-07-3
2-Hydroxy-2,7a-dimethyl-1a,7a-dihydro-2H-1-oxa-cyclopropa[b]naphthalen-7-one

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With 18-crown-6 ether; diethyl adipate; oxygen In tetrahydrofuran for 3h; Ambient temperature;	A 60% B 35%

: 141-28-6
diethyl adipate

: 125541-06-2
potassium 2,4-dimethyl-1-naphthoxide

A: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 125541-07-3
(1aR,2R,7aR)-2-Hydroxy-2,7a-dimethyl-1a,7a-dihydro-2H-1-oxa-cyclopropa[b]naphthalen-7-one

Conditions

Conditions	Yield
With 18-crown-6 ether; oxygen In tetrahydrofuran for 0.5h; Mechanism;	A 31% B 51%

...Expand

: 39910-34-4
ethyl 2-diazo-2-(1-hydroxycyclobutyl)acetate

A: 27326-83-6
ethyl 2-phenyl-1-cyclopentene-1-carboxylate

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

C: ethyl 2-fluorocyclopent-1-ene carboxylate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; benzene at 5℃; for 2.5h;	A 51% B 32% C 5%

...Expand

: 39910-34-4
ethyl 2-diazo-2-(1-hydroxycyclobutyl)acetate

: 71-43-2
benzene

A: 27326-83-6
ethyl 2-phenyl-1-cyclopentene-1-carboxylate

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

C: ethyl 2-fluorocyclopent-1-ene carboxylate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at 5℃; for 2.5h;	A 51% B 32% C 5%

...Expand

: 5457-28-3
3-cyano-1H-indole

: 122539-74-6
2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester

A: 2-(3-cyanoindol-1-yl)cyclopent-1-enecarboxylic acid ethyl ester

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
Stage #1: 3-cyano-1H-indole With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In 1,4-dioxane; toluene at 60℃; for 0.5h; Stage #2: 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester In 1,4-dioxane; toluene at 60 - 95℃; for 7h;	A 18% B 50%

...Expand

: 122539-74-6
2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester

: 55-21-0
benzamide

A: 18227-13-9
2-Benzamido-cyclopent-1-en-carbonsaeure-ethylester

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With potassium tert-butylate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran; 1,4-dioxane at 80℃;	A 47% B n/a

...Expand

: 64-17-5
ethanol

: 53007-35-5
1,1,4-butanetricarboxylic acid triethyl ester

: 141-52-6
sodium ethanolate

A: 51657-17-1
diethyl cyclopentanone-2,5-dicarboxylate

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

...Expand

: 53007-35-5
1,1,4-butanetricarboxylic acid triethyl ester

A: 51657-17-1
diethyl cyclopentanone-2,5-dicarboxylate

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With ethanol; sodium ethanolate

: 4450-43-5
butane-1,1,4,4-tetracarboxylic acid tetraethyl ester

: 141-52-6
sodium ethanolate

A: 51657-17-1
diethyl cyclopentanone-2,5-dicarboxylate

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

...Expand

: 111-50-2
Adipic acid dichloride

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

Conditions

Conditions	Yield
With triethylamine; benzene Behandeln der Reaktionsloesung mit Chlorwasserstoff enthaltendem Aethanol;

: 52909-66-7
ethyl 2-(N-phenylamino)-1-cyclopentene-1-carboxylate

A: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

B: 62-53-3
aniline

Conditions

Conditions	Yield
With water at 25℃; Rate constant; Mechanism; presence and absence of various enzyme systems; pH range: 1-9;

: 163559-10-2
ethyl 5-(N-methoxy-N-methylcarbamoyl)pentanoate

A: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

B: 2-Oxo-cyclopentanecarboxylic acid methoxy-methyl-amide

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Yield given. Yields of byproduct given;

: 111-50-2
Adipic acid dichloride

: 121-44-8
triethylamine

: 71-43-2
benzene

A: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

B 5-oxo-nonane-dicarboxylic acid-(1.9)-diethyl ester: 5-oxo-nonane-dicarboxylic acid-(1.9)-diethyl ester

Conditions

Conditions	Yield
beim ein unbestaendiges Produkt, das bei der Umsetzung mit Aethanol und wenig HCl;

...Expand

: 64-17-5
ethanol

: 141-28-6
diethyl adipate

sodium: sodium

A: 629-11-8
1,6-hexanediol

B: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

...Expand

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 62-53-3
aniline

: 4874-65-1
2-(N-phenylcarbamoyl)cyclopentanone

Conditions

Conditions	Yield
In neat (no solvent) at 180℃; for 0.75h; Microwave irradiation; Green chemistry;	100%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; Inert atmosphere;	90%
With dmap In toluene for 9.5h; Reflux; Inert atmosphere;	39%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 61586-79-6
ethyl (1R,2S)-2-hydroxycyclopentanecarboxylate

Conditions

Conditions	Yield
In ethanol at 25℃; prepared by Geotrichum candidum;	100%
With Mucor racemosus yeast	100%
With nicotinamide adenine dinucleotide In aq. buffer at 30℃; pH=6.5; Reagent/catalyst; Inert atmosphere; Enzymatic reaction; enantioselective reaction;	95%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine

: 130655-36-6
2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclopent-1-enecarboxylic acid ethyl ester

Conditions

Conditions	Yield
In ethanol at 100℃; for 1.33333h;	100%
In ethanol at 100℃; for 2h;
In chloroform at 70℃; Molecular sieve;

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 78-94-4
methyl vinyl ketone

: 58623-79-3, 69586-18-1, 74627-01-3, 61771-81-1
2-ethoxycarbonyl-2-(3-oxobutyl)cyclopentanone

Conditions

Conditions	Yield
europium-containing poly(2,4-OH2-C6H4COO--co-HCHO)-gel In dichloromethane at 20℃; for 4.5h; Michael addition;	100%
With iron(III) perchlorate at 23℃; for 12h; Product distribution; Further Variations:; Reagents;	99%
With Fe3+-exchanged fluorotetrasilicic mica at 20℃; for 20h; Michael reaction;	99%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 84131-44-2
1-fluoro-2-oxocyclopentane-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With N-fluorobis<(trifluoromethyl)sulfonyl>imide In dichloromethane at 22℃; for 4h;	100%
With N-fluorobis<(trifluoromethyl)sulfonyl>imide In dichloromethane at 22℃; for 4h;	100%
With Genapol LRO; Selectfluor In water at 60℃;	87%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 82415-38-1
ethyl 1-hydroxy-2-oxo-1-cyclopentanecarboxylate

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In acetone at 20℃; for 72h;	100%
With cerium(III) chloride; oxygen In isopropyl alcohol at 23℃; for 16h;	99%
With cerium(III) chloride; oxygen In isopropyl alcohol at 23℃; for 16h;	99%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 107-08-4
1-iodo-propane

: 56197-54-7
2-oxo-1-propyl-cyclopentanecarboxylic acid ethyl ester

Conditions

Conditions	Yield
With sodium hydride In toluene 1.) room temp., 15 min, 2.) reflux, 48 h;	100%

: 3674-09-7, 132854-28-5
methyl 2,3-dichloropropionate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: methyl 2-chloro-3-[1-(ethoxycarbonyl)-2-oxocyclopentyl]propanoate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0℃;	100%

: 693-67-4
bromoundecane

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 553668-26-1
ethyl 2-oxo-1-(n-undecyl)cyclopentanecarboxylate

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetone for 20h; Heating;	100%
With potassium carbonate; potassium iodide In acetone for 20h; Heating;	93%

: 848778-96-1
acetic acid 1-acetoxy-2-benzenesulfonyl-allyl ester

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 1-((E)-3-Acetoxy-2-benzenesulfonyl-allyl)-2-oxo-cyclopentanecarboxylic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 2-ethoxycarbonyl-1-cyclopentanone With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: acetic acid 1-acetoxy-2-benzenesulfonyl-allyl ester In tetrahydrofuran for 1h; Michael addition;	100%

: 67-56-1
methanol

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 209852-02-8
1-ethyl 6-methyl 2-methylenehexanedioate

Conditions

Conditions	Yield
Stage #1: methanol With dihydrogen peroxide; benzaldehyde; iron(III)-acetylacetonate at 20℃; for 0.666667h; Stage #2: 2-ethoxycarbonyl-1-cyclopentanone With diethyl amine hydrochloride	100%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 870-50-8
di-tert-butyl (E)-azodicarboxylate

: 921040-47-3
(R)-N,N'-bis(tert-butoxycarbonyl)-1-hydrazino-2-oxocyclopentanecarboxylic acid ethyl ester

Conditions

Conditions	Yield
With axially chiral guanidine derivative In tetrahydrofuran at -60℃; for 0.0833333h;	100%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 3156-51-2
3-(2-nitroethenyl)-1H-indole

: ethyl-1-[1-(1H-indol-3-yl)-2-nitro-ethyl]-2-oxocyclopentanecarboxylate

Conditions

Conditions	Yield
With sodium acetate at 20℃; for 2h; Michael type addition; Sonication; Neat (no solvent); optical yield given as %de;	100%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 371-40-4
4-fluoroaniline

: 1416585-27-7
C14H18FNO2

Conditions

Conditions	Yield
With acetic acid; zinc In water at 80℃; for 2h; Inert atmosphere;	100%
Stage #1: 2-ethoxycarbonyl-1-cyclopentanone; 4-fluoroaniline With acetic acid; zinc In water at 80℃; for 2h; Stage #2: With ammonium hydroxide pH=10;

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 74-88-4
methyl iodide

: 172825-15-9
ethyl-1-methyl-2-oxocyclopentane-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-ethoxycarbonyl-1-cyclopentanone; methyl iodide With potassium carbonate In acetone at 60℃; for 18h; Inert atmosphere; Schlenk technique; Stage #2: With triethylamine at 20℃; Inert atmosphere; Schlenk technique;	100%

: 110-91-8
morpholine

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 65520-21-0
2-(morpholine-4-carbonyl) cyclopentanone

Conditions

Conditions	Yield
In neat (no solvent) at 180℃; for 0.5h; Microwave irradiation; Green chemistry;	100%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 104-94-9
4-methoxy-aniline

: 94091-87-9
2-(4-methoxyphenylamino)-cyclopent-1-enecarboxylic acid ethyl ester

Conditions

Conditions	Yield
ammonium cerium(IV) nitrate In ethanol at 20℃; for 1.5h;	99%
indium(III) bromide at 20℃; for 1.66667h;	94%
zirconium(IV) chloride at 20℃; for 1.33333h;	93%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 106-95-6
allyl bromide

: 41975-67-1
1-allyl-2-oxo-cyclopentanecarboxylic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 20h; Reflux;	99%
Stage #1: 2-ethoxycarbonyl-1-cyclopentanone With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Stage #2: allyl bromide In tetrahydrofuran; mineral oil at 20℃;	98%
With potassium carbonate In acetone at 60℃; for 20h;	98%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 62-53-3
aniline

: 52909-66-7
ethyl 2-(N-phenylamino)-1-cyclopentene-1-carboxylate

Conditions

Conditions	Yield
With silica gel at 20℃; for 24h;	99%
With zinc(II) perchlorate; magnesium sulfate In dichloromethane at 20℃; for 5h;	99%
With zinc diacetate; magnesium sulfate In dichloromethane for 48h; Heating;	99%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 140-88-5
ethyl acrylate

: 57026-64-9
ethyl 1-(2-ethoxycarbonylethyl)-2-oxocyclopentanecarboxylate

Conditions

Conditions	Yield
With trifluoroacetic acid at 20℃; for 5h; Addition; Michael addition;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 0.0833333h; Michael addition;	99%
With [1-(methyl)-3-N-(benzylacetamido)imidazol-2-ylidene]2Ni In acetonitrile at 20℃; for 16h; Michael addition;	99%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 7149-18-0
ethyl 2-amino-1-cyclopentene-1-carboxylate

Conditions

Conditions	Yield
With ammonia; silica gel at 20℃; for 0.166667h;	99%
With ammonium acetate; tetraethoxy orthosilicate In ethanol Heating;	90%
With tetraethoxy orthosilicate; ammonium acetate In ethanol for 6h; Reflux; Inert atmosphere;	82%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 100-46-9
benzylamine

: 10412-92-7
ethyl 2-(benzylamino)cyclopent-1-ene-1-carboxylate

Conditions

Conditions	Yield
With silica gel at 20℃; for 0.166667h;	99%
at 55℃; under 22.5023 Torr; for 2h;	96%
With zinc diacetate; magnesium sulfate In dichloromethane at 20℃; for 16h;	90%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 42593-11-3
ethyl 1-bromo-2-oxocyclopentanecarboxylate

Conditions

Conditions	Yield
Stage #1: 2-ethoxycarbonyl-1-cyclopentanone With copper(II) bis(trifluoromethanesulfonate); (S)-N-[2-(2,4,6-triisopropylbenzylamino)phenyl]-S-methyl-S-phenylsulfoximine In diethyl ether at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In diethyl ether at -78 - 20℃; for 16h; Inert atmosphere;	99%
With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.333333h;	97%
With ammonium bromide; dihydrogen peroxide; vanadia In dichloromethane; water at 0 - 5℃; for 3.5h;	87%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 459-73-4
GlyOEt*HCl

: 74477-56-8
2-Ethoxycarbonylmethylamino-1-cyclopentencarbonsaeure-ethylester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 60℃; for 0.0166667h;	99%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 87420-26-6
(1R,2S,3R)-3-[N-Phenylsulfonyl-N-(3,5-dimethylphenyl)amino]bornan-2-ol

: 448961-10-2
(1R,2S,3R,4S)-<3--2-bornyl>-2-oxo-cyclopentane-carboxylate

Conditions

Conditions	Yield
With dmap In toluene for 48h; Heating;	99%
With dmap In toluene for 48h; Heating;	99%

: 1629-58-9
4-penten-3-one

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: ethyl 2-oxo-1-(3-oxopentyl)cyclopentane-1-carboxylate

Conditions

Conditions	Yield
With Fe-mica; moisture at 20℃; for 20h; Michael reaction;	99%
With Fe3+-exchanged fluorotetrasilicic mica at 20℃; for 20h; Michael reaction;	99%
With silica gel In neat (no solvent) at 0 - 70℃; for 24h; Michael Addition;	99%

: 930-30-3
cyclopent-2-enone

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: ethyl 2-oxo-(3-oxocyclopentyl)cyclopentanecarboxylate

Conditions

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%

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 292638-85-8
acrylic acid methyl ester

: 177664-80-1
1-(ethoxycarbonyl)-2-oxocyclopentanepropanoic acid methyl ester

Conditions

Conditions	Yield
With [(CH2)2N[(CH2)3N[(CH2)3NHC(O)]2]2]2-azidophosphine dendrimer In acetonitrile at 20℃; for 25h; Michael addition;	99%
With [1-(i-propyl)-3-N-(benzylacetamido)imidazol-2-ylidene]2Ni In acetonitrile at 20℃; for 16h; Michael addition;	96%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 0.166667h; Michael addition;	94%

: 591-87-7
Allyl acetate

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 41975-67-1
1-allyl-2-oxo-cyclopentanecarboxylic acid ethyl ester

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); N,N,N',N'-tetramethylguanidine In toluene at 20℃; for 24h; allylation;	99%
With tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether; carbon dioxide; potassium carbonate at 75℃; under 129209 Torr; for 18h; Tsuji-Trost Allylation; Supercritical conditions; Autoclave;	64%

Ethyl 2-oxocyclopentanecarboxylate Specification

The IUPAC name of this chemical is ethyl 2-oxocyclopentane-1-carboxylate. With the CAS registry number 611-10-9, it is also named as Cyclopentanecarboxylic acid, 2-oxo-, ethyl ester. The product's categories are pharmaceutical intermediates; building blocks. Ethyl 2-oxocyclopentanecarboxylate is clear colourless to pale yellow liquid which is soluble in alcohol, ether, benzene, and insoluble in water. As its usage, it is used as intermediate in pharmaceutical synthesis and organic synthesis. And it is also used as flavor additive.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.26; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.26; (4)ACD/LogD (pH 7.4): 0.26; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 32.9; (8)ACD/KOC (pH 7.4): 32.9; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.468; (13)Molar Refractivity: 38.77 cm³; (14)Molar Volume: 139.3 cm³; (15)Polarizability: 15.37×10^-24 cm³; (16)Surface Tension: 39.5 dyne/cm; (17)Enthalpy of Vaporization: 46.48 kJ/mol; (18)Vapour Pressure: 0.0743 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Tautomer Count: 5; (21)Exact Mass: 156.078644; (22)MonoIsotopic Mass: 156.078644; (23)Topological Polar Surface Area: 43.4; (24)Heavy Atom Count: 11; (25)Complexity: 174.

Preparation of Ethyl 2-oxocyclopentanecarboxylate: It is obtained by the cyclization of hexanedioic acid diethyl ester in toluene and in the presence of sodium. The reaction temperature is 100-115 °C , reaction time is 5h, and the yield is 74-81%.

Uses of Ethyl 2-oxocyclopentanecarboxylate: It can be used in the preparation of Loxoprofen sodium. It reacts with ethyl 2-(4-chloromethylphenyl)propionate (II) by means of KOH in hot DMF gives ethyl 2-[4-(1-ethoxycarbonyl-2-oxocyclopentan-1-ylmethyl)phenyl]propionate (III), which is then hydrolyzed and decarboxylated by treatment with 47% HBr in refluxing dioxane.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin, so people should not breathe vapour and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and gloves.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C(OCC)C1C(=O)CCC1;
2. InChI: InChI=1/C8H12O3/c1-2-11-8(10)6-4-3-5-7(6)9/h6H,2-5H2,1H3.

Product Name

Ethyl 2-oxocyclopentanecarboxylate

Synthetic route

Ethyl 2-oxocyclopentanecarboxylate Specification

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