Products Categories
CAS No.: | 4429-63-4 |
---|---|
Name: | TABERSONINE |
Article Data: | 17 |
Molecular Structure: | |
Formula: | C21H24N2O2 |
Molecular Weight: | 336.434 |
Synonyms: | 1H-Indolizino[8,1-cd]carbazole-5-carboxylicacid, 3a-ethyl-3a,4,6,11,12,13a-hexahydro-, methyl ester (7CI);Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-, methyl ester, (5a,12b,19a)-;Tabersonine (8CI);(-)-Tabersonine;Tabersonin; |
EINECS: | 224-615-0 |
Density: | 1.27 g/cm3 |
Melting Point: | 196 °C |
Boiling Point: | 488.7 °C at 760 mmHg |
Flash Point: | 249.4 °C |
Appearance: | Yellow to brownish powder, pungent odour |
PSA: | 41.57000 |
LogP: | 3.29710 |
19-Iodo-tabersonine
tabersonine
Conditions | Yield |
---|---|
With sodium hydroxide; hydrogen; nickel In methanol at 0℃; for 0.0833333h; | 90% |
methyl (2S,3aR,3a1S,10bR)-3a-ethyl-2-hydroxy-2,3,3a,3a1,4,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate
tabersonine
Conditions | Yield |
---|---|
With triphenylphosphine In tetrachloromethane; acetonitrile at 70℃; for 0.5h; | 73% |
With triphenylphosphine In tetrachloromethane; acetonitrile at 70℃; for 0.5h; | 71% |
With triphenylphosphine In tetrachloromethane; acetonitrile at 70℃; for 0.5h; Inert atmosphere; | 64% |
methyl cyanoformate
(-)-1,2,14,15-tetradehydroaspidospermidine
tabersonine
Conditions | Yield |
---|---|
Stage #1: (-)-1,2,14,15-tetradehydroaspidospermidine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: methyl cyanoformate In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; | 73% |
With lithium diisopropyl amide In tetrahydrofuran at -78℃; | 73% |
Conditions | Yield |
---|---|
In acetonitrile at 30℃; Irradiation; Title compound not separated from byproducts; | A n/a B 10% |
(S)-3a-Ethyl-2-hydroxy-2,3,3a,4,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester
tabersonine
Conditions | Yield |
---|---|
With tetrachloromethane; triphenylphosphine In acetonitrile |
tabersonine N4-oxide
tabersonine
Conditions | Yield |
---|---|
With iron(II) sulfate for 0.25h; Heating; | 0.5 mg |
16-epi-19-S-vindolinine
tabersonine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / 10percent Na2CO3, I2 / tetrahydrofuran; H2O / 1 h / Ambient temperature 2: 90 percent / H2, NaOH / Raney Nickel / methanol / 0.08 h / 0 °C View Scheme |
5-chloro-2-ethyl-(4S)-hydroxypentanal lactol
tabersonine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) boric acid, 2.) triethylamine / 1.) methanol, reflux, 24 h, 2.) methanol, reflux, 12 h 2: 71 percent / triphenylphosphine / acetonitrile; CCl4 / 0.5 h / 70 °C View Scheme |
methyl 1,2,3,4,5,6-hexahydroazepino<4,5-b>indole-5-carboxylate
tabersonine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) boric acid, 2.) triethylamine / 1.) methanol, reflux, 24 h, 2.) methanol, reflux, 12 h 2: 71 percent / triphenylphosphine / acetonitrile; CCl4 / 0.5 h / 70 °C View Scheme |
1-(benzenesulfonyl)-2-methyl-1H-indole-3-carbaldehyde
tabersonine
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 0.67 h / -15 °C / Inert atmosphere 3.2: 2 h / -15 °C / Inert atmosphere 4.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere 5.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C / Inert atmosphere 6.2: 2 h / -78 - 20 °C / Inert atmosphere 7.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 48 h / 20 °C / Inert atmosphere 8.1: hydrogenchloride / methanol; water / 0 °C / Inert atmosphere 9.1: sodium carbonate / ethanol / 24 h / 85 °C / Inert atmosphere 10.1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 11.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 11.2: 1 h / -78 °C / Inert atmosphere View Scheme |
Molecular structure of Tabersonine (CAS NO.4429-63-4) is:
Product Name: Tabersonine
CAS Registry Number: 4429-63-4
Molecular Weight: 336.42746 [g/mol]
Molecular Formula: C21H24N2O2
XLogP3-AA: 3.4
H-Bond Donor: 1
H-Bond Acceptor: 4
EINECS: 224-615-0
Index of Refraction: 1.651
Molar Refractivity: 96.78 cm3
Molar Volume: 264.7 cm3
Surface Tension: 55.7 dyne/cm
Density: 1.27 g/cm3
Flash Point: 249.4 °C
Enthalpy of Vaporization: 75.48 kJ/mol
Boiling Point: 488.7 °C at 760 mmHg
Vapour Pressure: 1.06E-09 mmHg at 25°C
Classification Code: Drug / Therapeutic Agent
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | Annales Pharmaceutiques Francaises. Vol. 13, Pg. 123, 1955. |
Tabersonine , its cas register number is 4429-63-4. It also can be called Tabersonin ; Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-,methyl ester, (5alpha,12beta,19alpha)- ; Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetrahydro-,methyl ester, (5-alpha,12-beta,19-alpha)- .It is a yellow to brownish powder with pungent odour .