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Tabersonine
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Name

Tabersonine

 EINECS 224-615-0
CAS No. 4429-63-4 Density 1.27 g/cm3
PSA 41.57000 LogP 3.29710
Solubility N/A Melting Point 196 °C
Formula C21H24N2O2 Boiling Point 488.7 °C at 760 mmHg
Molecular Weight 336.434 Flash Point 249.4 °C
Transport Information N/A Appearance Yellow to brownish powder, pungent odour
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 4429-63-4 (TABERSONINE) Hazard Symbols N/A
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;

Article Data 17

Tabersonine Synthetic route

55856-70-7

19-Iodo-tabersonine

4429-63-4

tabersonine

Conditions
ConditionsYield
With sodium hydroxide; hydrogen; nickel In methanol at 0℃; for 0.0833333h;90%
62414-79-3

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

4429-63-4

tabersonine

Conditions
ConditionsYield
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%
17640-15-2

methyl cyanoformate

32975-46-5

(-)-1,2,14,15-tetradehydroaspidospermidine

4429-63-4

tabersonine

Conditions
ConditionsYield
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%
91201-53-5

C21H24N2O2

A

4429-63-4

tabersonine

B

1,2-seco-1,21-cyclotabersonine

Conditions
ConditionsYield
In acetonitrile at 30℃; Irradiation; Title compound not separated from byproducts;A n/a
B 10%
62414-79-3, 63490-95-9, 74165-08-5, 80695-59-6, 80695-62-1, 95042-67-4

(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

4429-63-4

tabersonine

Conditions
ConditionsYield
With tetrachloromethane; triphenylphosphine In acetonitrile
67249-34-7

tabersonine N4-oxide

4429-63-4

tabersonine

Conditions
ConditionsYield
With iron(II) sulfate for 0.25h; Heating;0.5 mg
41787-54-6

16-epi-19-S-vindolinine

4429-63-4

tabersonine

Conditions
ConditionsYield
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
80642-07-5

5-chloro-2-ethyl-(4S)-hydroxypentanal lactol

4429-63-4

tabersonine

Conditions
ConditionsYield
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
66859-22-1

methyl 1,2,3,4,5,6-hexahydroazepino<4,5-b>indole-5-carboxylate

4429-63-4

tabersonine

Conditions
ConditionsYield
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
124293-81-8

1-(benzenesulfonyl)-2-methyl-1H-indole-3-carbaldehyde

4429-63-4

tabersonine

Conditions
ConditionsYield
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

Tabersonine Chemical Properties

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

Tabersonine Toxicity Data With Reference

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 Specification

 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 .

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