Product Name

  • Name

    3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER

  • EINECS
  • CAS No. 24922-00-7
  • Article Data14
  • CAS DataBase
  • Density 1.065 g/cm3
  • Solubility
  • Melting Point
  • Formula C10H16O3
  • Boiling Point 255.3 °C at 760 mmHg
  • Molecular Weight 184.235
  • Flash Point 106.1 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 24922-00-7 (3-CYCLOPENTYL-3-OXO-PROPIONIC ACID ETHYL ESTER)
  • Hazard Symbols
  • Synonyms Cyclopentanepropionicacid, b-oxo-, ethyl ester (8CI);Ethyl3-Cyclopentyl-3-oxopropanoate;Ethyl 3-cyclopentyl-3-oxopropionate;
  • PSA 43.37000
  • LogP 1.69890

Synthetic route

6-bicyclo<3.1.0>hexan-6-ol
71911-64-3

6-bicyclo<3.1.0>hexan-6-ol

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
In neat (no solvent) at 110℃;99%
3-cyclopentyl-2-diazo-3-hydroxy-propionic acid ethyl ester
811467-21-7

3-cyclopentyl-2-diazo-3-hydroxy-propionic acid ethyl ester

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
With copper(II) sulfate at 20℃; for 3h;91%
Cyclopentanecarboxylic acid chloride
4524-93-0

Cyclopentanecarboxylic acid chloride

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
Stage #1: hydrogen ethyl malonate With [2,2]bipyridinyl; n-butyllithium In hexanes at -65 - -55℃;
Stage #2: Cyclopentanecarboxylic acid chloride In hexanes at 20℃;		89%
Multi-step reaction with 2 steps
1: pyridine / CH2Cl2 / 2 h / 0 - 20 °C
2: toluene / 24 h / 80 °C
View Scheme
Cyclopentanecarboxylic acid chloride
4524-93-0

Cyclopentanecarboxylic acid chloride

ethyl potassium malonate
6148-64-7

ethyl potassium malonate

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
With triethylamine; magnesium chloride In acetonitrile at 0℃; for 4h;77%
6-bicyclo<3.1.0>hexan-6-ol
71911-61-0

6-bicyclo<3.1.0>hexan-6-ol

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
at 300℃; for 1h;52%
2-cyclopentanecarbonyl-3-oxo-butyric acid ethyl ester
412018-99-6

2-cyclopentanecarbonyl-3-oxo-butyric acid ethyl ester

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
With diethyl ether; ammonia
1-cyclopentylethanone
6004-60-0

1-cyclopentylethanone

Diethyl carbonate
105-58-8

Diethyl carbonate

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
With sodium amide
ethanol
64-17-5

ethanol

5-(cyclopentanecarbonyl)2,2-dimethyl-1,3-dioxane-4,6-dione
134302-12-8

5-(cyclopentanecarbonyl)2,2-dimethyl-1,3-dioxane-4,6-dione

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
In toluene at 80℃; for 24h; Yield given;
diethyl malonate
105-53-3

diethyl malonate

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) Na / 1. benzene, reflux, 8 h; 2. 2h at 0 deg C, then 6 h room temp.
2: 52 percent / 1 h / 300 °C
View Scheme
Cyclopentanecarboxylic acid chloride
4524-93-0

Cyclopentanecarboxylic acid chloride

ethyl acetate
141-78-6

ethyl acetate

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

Conditions
ConditionsYield
Stage #1: ethyl acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere;
Stage #2: Cyclopentanecarboxylic acid chloride In tetrahydrofuran; hexane at -78℃; for 0.0833333h;
Cyclopentanecarboxylic acid chloride
4524-93-0

Cyclopentanecarboxylic acid chloride

ethyl acetate
141-78-6

ethyl acetate

A

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

B

C10H16O3

C10H16O3

Conditions
ConditionsYield
Stage #1: ethyl acetate With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: Cyclopentanecarboxylic acid chloride In tetrahydrofuran at -78℃; for 2h; Overall yield = 643 mg;
...Expand
cyclopentanecarboxylic acid
3400-45-1

cyclopentanecarboxylic acid

A

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

B

C10H16O3

C10H16O3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C
2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C
2.2: 2 h / -78 °C
View Scheme
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

guanidine hydrochloride
50-01-1

guanidine hydrochloride

2-amino-6-cyclopentyl-4-hydroxypyrimidine

2-amino-6-cyclopentyl-4-hydroxypyrimidine

Conditions
ConditionsYield
With potassium tert-butylate In methanol at 23 - 60℃;88%
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

guanidine hydrochloride
50-01-1

guanidine hydrochloride

2-amino-6-cyclopentyl-3H-pyrimidin-4-one
199863-76-8

2-amino-6-cyclopentyl-3H-pyrimidin-4-one

Conditions
ConditionsYield
Stage #1: ethyl 3-cyclopentyl-3-oxopropionate; guanidine hydrochloride With potassium tert-butylate In methanol at 20 - 60℃;
Stage #2: With hydrogenchloride In methanol; water pH=5;		87%
With potassium tert-butylate In methanol at 23 - 60℃;
2,6-di-tert-butyl-4-(4-methoxybenzylidene)-cyclohexa-2,5-dienone
71711-98-3

2,6-di-tert-butyl-4-(4-methoxybenzylidene)-cyclohexa-2,5-dienone

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

C32H44O5

C32H44O5

Conditions
ConditionsYield
With C51H62N2O2; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at -15℃; for 18h; enantioselective reaction;86%
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

3-cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester
1046450-99-0

3-cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester

Conditions
ConditionsYield
Stage #1: ethyl 3-cyclopentyl-3-oxopropionate With [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate In methanol at 20℃;
Stage #2: With water; sodium hydrogencarbonate In dichloromethane		43%
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

acetic acid
64-19-7

acetic acid

2-amino-1-cyclopentyl-ethanone
89895-04-5

2-amino-1-cyclopentyl-ethanone

Conditions
ConditionsYield
With sodium nitrite Behandeln des Reaktionsprodukts mit Zink und Acetanhydrid unter Zusatz von Eis und Erhitzen des danach isolierten Reaktionsprodukts mit wss. Salzsaeure;
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

thiourea
17356-08-0

thiourea

6-cyclopentyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

6-cyclopentyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

Conditions
ConditionsYield
With ethanol; sodium ethanolate
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

A

5-cyclopentylisoxazol-3-ol
27772-74-3

5-cyclopentylisoxazol-3-ol

B

3-cyclopentyl-2H-isoxazol-5-one
29068-27-7

3-cyclopentyl-2H-isoxazol-5-one

Conditions
ConditionsYield
(i) NH2OH*HCl, aq. NaOH, (ii) aq. HCl; Multistep reaction;
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

3-cyclopentyl-2H-isoxazol-5-one
29871-87-2

3-cyclopentyl-2H-isoxazol-5-one

Conditions
ConditionsYield
With hydroxylamine hydrochloride
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

ethyl bromoacetate
105-36-2

ethyl bromoacetate

diethyl 2-(cyclopentanecarbonyl)succinate
1057673-87-6

diethyl 2-(cyclopentanecarbonyl)succinate

Conditions
ConditionsYield
With sodium In ethanol
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

4-methoxybenzoic acid hydrazide
3290-99-1

4-methoxybenzoic acid hydrazide

3-Cyclopentyl-3-[(4-methoxy-benzoyl)-hydrazono]-propionic acid ethyl ester

3-Cyclopentyl-3-[(4-methoxy-benzoyl)-hydrazono]-propionic acid ethyl ester

Conditions
ConditionsYield
In isopropyl alcohol for 0.5h; Heating;
2,6-dichlorobenzohydroximoyl chloride
6579-27-7

2,6-dichlorobenzohydroximoyl chloride

ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

ethyl 5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate
1020568-84-6

ethyl 5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolecarboxylate

Conditions
ConditionsYield
With sodium ethanolate In tetrahydrofuran; ethanol at 0 - 20℃;
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

4-cyclopentyl-4-oxobutanoic acid
3400-90-6

4-cyclopentyl-4-oxobutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Na / ethanol
2: aq. HCl
View Scheme
ethyl 3-cyclopentyl-3-oxopropionate
24922-00-7

ethyl 3-cyclopentyl-3-oxopropionate

3-cyclopentyl-5-methoxy-isoxazole
29871-78-1

3-cyclopentyl-5-methoxy-isoxazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH2OH*HCl
View Scheme

Ethyl 3-cyclopentyl-3-oxopropanoate Specification

The CAS register number of Ethyl 3-cyclopentyl-3-oxopropanoate is 24922-00-7. It also can be called as Cyclopentanepropanoicacid, b-oxo-, ethyl ester and the IUPAC name about this chemical is ethyl 3-cyclopentyl-3-oxopropanoate. The molecular formula about this chemical is C10H16O3 and molecular weight is 184.23 .

Physical properties about Ethyl 3-cyclopentyl-3-oxopropanoate are: (1)ACD/LogP: 2.21; (2)ACD/LogD (pH 5.5): 2.21; (3)ACD/LogD (pH 7.4): 2.21; (4)ACD/BCF (pH 5.5): 28.23; (5)ACD/BCF (pH 7.4): 28.21; (6)ACD/KOC (pH 5.5): 380.19; (7)ACD/KOC (pH 7.4): 379.9; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 43.37Å2; (11)Index of Refraction: 1.466; (12)Molar Refractivity: 47.93 cm3; (13)Molar Volume: 172.9 cm3; (14)Polarizability: 19x10-24cm3; (15)Surface Tension: 38 dyne/cm; (16)Enthalpy of Vaporization: 49.27 kJ/mol; (17)Boiling Point: 255.3 °C at 760 mmHg; (18)Vapour Pressure: 0.0165 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(CC(=O)OCC)C1CCCC1
(2)InChI: InChI=1/C10H16O3/c1-2-13-10(12)7-9(11)8-5-3-4-6-8/h8H,2-7H2,1H3
(3)InChIKey: MUDKQMLLCRJCEY-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C10H16O3/c1-2-13-10(12)7-9(11)8-5-3-4-6-8/h8H,2-7H2,1H3
(5)Std. InChIKey: MUDKQMLLCRJCEY-UHFFFAOYSA-N

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