Basic Information | Post buying leads | Suppliers | Cas Database |
Name |
Oseltamivir |
EINECS | 1308068-626-2 |
CAS No. | 196618-13-0 | Density | 1.08 g/cm3 |
PSA | 90.65000 | LogP | 2.37660 |
Solubility | Soluble | Melting Point |
107-108 °C |
Formula | C16H28N2O4 | Boiling Point | 473.3 °C at 760 mmHg |
Molecular Weight | 312.409 | Flash Point | 240 °C |
Transport Information | N/A | Appearance | N/A |
Safety | Risk Codes | N/A | |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, [3R-(3a,4b,5a)]-;GOP-A-Flu;GS 4104;Tamiflu-Free;Tamvir; |
Article Data | 66 |
oseltamivir
Conditions | Yield |
---|---|
With 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; for 2.21667h; | 88.7% |
Stage #1: ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate With 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine In ethanol at 35℃; for 2h; Inert atmosphere; Stage #2: With phosphoric acid In acetone for 2h; | 83.69% |
With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid |
(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
oseltamivir
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Inert atmosphere; | 92% |
Stage #1: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate With hydrogenchloride; water In ethanol at 50℃; for 1h; Stage #2: With sodium hydrogencarbonate In water | 90% |
With hydrogenchloride In tetrahydrofuran; ethyl acetate for 0.05h; | 13.8 mg |
ethyl (3R,4R,5S)-4-N-acetylamino-5-N-allylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate
oseltamivir
Conditions | Yield |
---|---|
With ethanolamine; palladium 10% on activated carbon In ethanol at 20℃; for 3h; Heating / reflux; | 70% |
With palladium on activated charcoal; ethanolamine In ethanol for 3h; Heating; | |
With ethanolamine; palladium on activated charcoal In ethanol for 3h; Heating; |
oseltamivir
Conditions | Yield |
---|---|
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 23 - 70℃; for 2h; Inert atmosphere; Stage #2: With ammonia In ethanol at 0℃; for 0.166667h; Stage #3: With potassium carbonate In ethanol at 23℃; for 6h; | 85% |
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 70℃; for 2h; Inert atmosphere; Stage #2: With ammonia In ethanol at 0℃; for 0.166667h; Inert atmosphere; Stage #3: With potassium carbonate In ethanol at 23℃; for 9h; Inert atmosphere; | 81% |
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 70℃; for 2h; Stage #2: With ammonia; potassium carbonate In ethanol at 20℃; for 6h; | 80% |
(3R,4R,5S)-4-acetamido-5-(1,3-dioxoisoindol-2-yl)-3-(pentyl-3-yloxy)cyclohexyl-ethyl-1-ene-1-carboxylate
oseltamivir
Conditions | Yield |
---|---|
With hydrazine In ethanol at 68℃; for 10h; | 100% |
With hydrazine In ethanol at 68℃; for 10h; Inert atmosphere; | 100% |
With hydrazine In ethanol at 68℃; for 11h; Schlenk technique; Inert atmosphere; | 86% |
oseltamivir
Conditions | Yield |
---|---|
With pyrrolidine; tetrakis(triphenylphosphine) palladium(0) In ethanol for 0.5h; | 95.1% |
With 1,3-dimethylbarbituric acid; triphenylphosphine; palladium on activated charcoal In ethanol; water at 80℃; for 1h; |
(3R,4R,5S)-ethyl-4-(N-acetylacetamide)-5-(1,3-dioxoisoindolin-2-yl)-3-(3-pentyloxy)cyclohex-1-ene carboxylate
oseltamivir
Conditions | Yield |
---|---|
Stage #1: (3R,4R,5S)-ethyl-4-(N-acetylacetamide)-5-(1,3-dioxoisoindolin-2-yl)-3-(3-pentyloxy)cyclohex-1-ene carboxylate With hydrazine hydrate In ethanol at 50℃; for 14h; Inert atmosphere; Stage #2: With hydrogenchloride; water In ethanol Stage #3: With ammonium hydroxide In water pH=11; | 96% |
oseltamivir
Conditions | Yield |
---|---|
With trifluoroacetic acid In isopropyl alcohol at 0 - 30℃; for 7h; Solvent; Reagent/catalyst; Temperature; | 96% |
oseltamivir
oseltamivir
Conditions | Yield |
---|---|
With hydrogen at 20℃; under 380.026 Torr; for 3h; | 98.5% |
With tributylphosphine; acetic acid In ethanol; water at 5 - 25℃; for 5.5 - 9h; | 97% |
With triphenylphosphine In tetrahydrofuran; water at 50℃; for 10h; | 96% |
oseltamivir
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 23℃; for 4h; retro Michael reaction; | 91% |
With potassium carbonate In ethanol at 23℃; for 4h; Product distribution / selectivity; | 91% |
Stage #1: (1S,2R,3S,4R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)-2-(p-tolylthio)cyclohexanecarboxylate With ammonia In ethanol at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With potassium carbonate In ethanol at 23℃; for 6h; Inert atmosphere; | 45.2 mg |
The 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- , with cas register number of 196618-13-0, belongs to the classification codes of (1)anti-infective agents ; (2)antiviral agents ; (3)enzyme inhibitors ; (4)influenza treatment. It also has other names such as Oseltamivir ; Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate . Its IUPAC name is ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate . And its systematic name is also called ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate .
Physical properties of 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- are: (1) ACD/LogP: 1.50 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -1.02 ; (4) ACD/LogD (pH 7.4): 0.69 ; (5) ACD/BCF (pH 5.5): 1 ; (6) ACD/BCF (pH 7.4): 1.25 ; (7) ACD/KOC (pH 5.5): 1 ; (8) ACD/KOC (pH 7.4): 24.06 ; (9) #H bond acceptors: 6 ; (10) #H bond donors: 3 ; (11) #Freely Rotating Bonds: 9 ; (12) Index of Refraction: 1.502 ; (13) Molar Refractivity: 84.66 cm3 ; (14) Molar Volume: 286.7 cm3 ; (15) Surface Tension: 41.1 dyne/cm ; (16) Density: 1.08 g/cm3 ; (17) Flash Point: 240 °C ; (18) Enthalpy of Vaporization: 73.64 kJ/mol ; (19) Boiling Point: 473.3 °C at 760 mmHg ; (20) Vapour Pressure: 3.98E-09 mmHg at 25°C.
Uses of 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- : This compound is an acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits neuraminidase. It has been used as a drug for treatment of influenza.
You can still convert the following datas into molecular structure:
(1) SMILES:O=C(OCC)/C1=C/[C@@H](OC(CC)CC)[C@H](NC(=O)C)[C@@H](N)C1;
(2) InChI:InChI=1/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1;
(3) InChIKey:VSZGPKBBMSAYNT-RRFJBIMHBB