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| CAS No.: | 130929-57-6 |
|---|---|
| Name: | Entacapone |
| Molecular Structure: | |
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|
|
| Formula: | C14H15N3O5 |
| Molecular Weight: | 305.29 |
| Synonyms: | Entacom;OR 611;2-Propenamide,2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (E)-;(E)-Entacapone;Comtan; |
| Density: | 1.392 g/cm3 |
| Melting Point: | 162-163 °C |
| Boiling Point: | 526.6 °C at 760 mmHg |
| Flash Point: | 272.3 °C |
| Appearance: | Yellow crystalline solid |
| Hazard Symbols: |
 Xn, T, F
|
| Risk Codes: | R10; R20/21/22; R37/38; R41; R62; R38; R36/37/38 |
| PSA: | 130.38000 |
| LogP: | 2.30458 |
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- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 345317-61-5
(E)-2-cyano-N,N-diethyl-3-(3-pivaloyloxy-4-hydroxy-5-nitrophenyl)propenamide
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| With phosphate buffer at 37℃; pH=7.4; Kinetics; | 100% |
- 404860-98-6
(E)-2-cyano-N,N-diethyl-3-[3-t-butyloxycarbonyloxy-4-hydroxy-5-nitrophenyl]propenamide
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| With phosphate buffer at 37℃; pH=7.4; Kinetics; | 100% |
- 857629-78-8
(2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| Stage #1: (2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide With aluminum (III) chloride; triethylamine In dichloromethane at 0 - 5℃; for 3 - 4h; Heating / reflux; Stage #2: With hydrogenchloride In dichloromethane at 0 - 20℃; for 0.5h; | 98% |
| With aluminum (III) chloride; triethylamine In dichloromethane | 98% |
| Stage #1: (2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide With aluminum (III) chloride; triethylamine In tetrahydrofuran at 0℃; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 6h; Solvent; Temperature; Time; Cooling; | 92% |
- 146698-91-1
2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| With pyridine; aluminum (III) chloride In dichloromethane at 0 - 45℃; for 2.5h; | 94.1% |
- 1067233-93-5
3,4-dimethoxy entacapone
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| Stage #1: 3,4-dimethoxy entacapone With aluminum (III) chloride In N,N-dimethyl-formamide at 5 - 80℃; for 15h; Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide at 5 - 30℃; for 2.5h; Product distribution / selectivity; | 92% |
| Stage #1: 3,4-dimethoxy entacapone With pyridine; aluminum (III) chloride In N,N-dimethyl-formamide at 5 - 80℃; for 15h; Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide at 5 - 30℃; for 2h; Product distribution / selectivity; | 80% |
| Stage #1: 3,4-dimethoxy entacapone With boron tribromide In dichloromethane at -15 - 20℃; Stage #2: With water In dichloromethane for 0.5h; Product distribution / selectivity; | 74% |
| With aluminum (III) chloride In pyridine at 80℃; |
- 1047659-01-7
entacapone; piperidine salt
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; isopropyl alcohol at 20 - 30℃; | 91.1% |
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| With pyridine; aluminum (III) chloride In dichloromethane at 0 - 45℃; for 50h; | 87.3% |
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| With pyridine; aluminum (III) chloride In chloroform at 0℃; for 0.5h; Reflux; | 81.1% |
- 26391-06-0
2-cyano-N,N-diethylacetamide
- 116313-85-0
3,4-dihydroxy-5-nitrobenzaldehyde
- 130929-57-6
entacapone
| Conditions | Yield |
|---|---|
| Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With piperidine In 1,2-dimethoxyethane; n-heptane for 15 - 25h; Heating / reflux; Stage #2: In dichloromethane at 25 - 35℃; for 24h; Product distribution / selectivity; | 75% |
| With piperidine In isopropyl alcohol for 12 - 15h; Heating / reflux; | 75.5% |
| Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With acetic acid; diethylamine In toluene Knoevenagel Condensation; Stage #2: With hydrogen bromide In acetic acid; toluene at 20℃; | 73.8% |
- 26391-06-0
2-cyano-N,N-diethylacetamide
- 116313-85-0
3,4-dihydroxy-5-nitrobenzaldehyde
A
- 130929-57-6
entacapone
B
- 145195-63-7
(2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide
| Conditions | Yield |
|---|---|
| Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With piperidine In isopropyl alcohol for 12 - 15h; Heating / reflux; Stage #2: With acetic acid In isopropyl alcohol at 20℃; | A 75.5% B n/a |
| piperidine; methylamine hydrochloride In butan-1-ol at 82℃; for 4 - 5h; Product distribution / selectivity; | |
| piperidine; methylamine hydrochloride In i-Amyl alcohol at 89 - 90℃; for 3h; Product distribution / selectivity; |
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Specification
The Entacapone is an organic compound with the formula C14H15N3O5. The IUPAC name of this chemical is (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide. With the CAS registry number 130929-57-6, it is also named as 2-propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (2E)-. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a yellow crystalline solid, which is a drug that functions as a catechol-O-methyl transferase (COMT) inhibitor. It is used in the treatment of Parkinson's disease.
Physical properties about Entacapone are: (1)ACD/LogP: 2.38; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 0.36; (4)ACD/BCF (pH 5.5): 15.66; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 194.12; (7)ACD/KOC (pH 7.4): 4.46; (8)#H bond acceptors: 8; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 7; (11)Polar Surface Area: 108.38 Å2; (12)Index of Refraction: 1.641; (13)Molar Refractivity: 79.12 cm3; (14)Molar Volume: 219.2 cm3; (15)Polarizability: 31.36×10-24cm3; (16)Surface Tension: 68.1 dyne/cm; (17)Density: 1.392 g/cm3; (18)Flash Point: 272.3 °C; (19)Enthalpy of Vaporization: 83.11 kJ/mol; (20)Boiling Point: 526.6 °C at 760 mmHg; (21)Vapour Pressure: 1.05E-11 mmHg at 25°C.
Preparation: this chemical can be prepared by 3,4-dihydroxy-5-nitrobenzaldehyde and N, N-diethyl cyano acetamide. This reaction will need catalyst piperidine acetate. The yield is about 80%.
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You can still convert the following datas into molecular structure:
(1)SMILES: [O-][N+](=O)c1cc(\C=C(/C#N)C(=O)N(CC)CC)cc(O)c1O
(2)InChI: InChI=1/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
(3)InChIKey: JRURYQJSLYLRLN-BJMVGYQFBD
(4)Std. InChI: InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
(5)Std. InChIKey: JRURYQJSLYLRLN-BJMVGYQFSA-N