methyl (1S,12S,14S,15R,20R)-14-hydroxy-15-methyl-8,17-diazapentacyclo[10.7.1.01,9.02,7.017,20]icosa-2,4,6,9-tetraene-10-carboxylate
Grundinformationen
- CAS
62861-08-9- Standard-SMILES
COC(=O)C1=C2Nc3ccccc3[C@]23CCN2C[C@@H](C)[C@@H](O)C[C@H](C1)[C@@H]23- InChIKey
LHNRZSVXQWMCJY-JAGIDWHDSA-N- Summenformel
- C21H26N2O3
- Durchschnittliche Molmasse
- 354,4 g/mol
Namen und Bezeichner
- Bevorzugter Name
- methyl (1S,12S,14S,15R,20R)-14-hydroxy-15-methyl-8,17-diazapentacyclo[10.7.1.01,9.02,7.017,20]icosa-2,4,6,9-tetraene-10-carboxylate
- IUPAC
- methyl (1S,12S,14S,15R,20R)-14-hydroxy-15-methyl-8,17-diazapentacyclo[10.7.1.01,9.02,7.017,20]icosa-2,4,6,9-tetraene-10-carboxylate
- Englischer Name
- (5β,12S,19β)-2,3-Didehydro-7β-hydroxy-8β-methyl-8a-homo-20,21-dinoraspidospermidine-3-carboxylic acid methyl ester
- Summenformel
- C21H26N2O3
- Molmasse
- 354.44
Namen und Synonyme
Iboxyphylline2,3-Didehydro-7β-hydroxy-8β-methyl-8a-homo-20,21-dinoraspidospermidine-3-carboxylic acid methyl ester(5β,12S,19β)-2,3-Didehydro-7β-hydroxy-8β-methyl-8a-homo-20,21-dinoraspidospermidine-3-carboxylic acid methyl esterIndolo[2,3-i]pyrrolo[3,2,1-jk][1]benzazepine-6-carboxylic acid, 1,2,3,4,4a,5,7,12,13,14a-decahydro-3-hydroxy-2-methyl-, methyl ester, (2R,3S,4aS,11bS,14aR)- (9CI)
Datenbank-Bezeichner
- CAS
62861-08-9- Nikkaji
- J18.275C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,6
- Polarare Oberfläche (TPSA)
- 61,8 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 647
Physikochemische Eigenschaften
- Schmelzpunkt
- 245 °C · 245°C
- Siedepunkt
- 533.4 · 533.4±50.0 °C(Predicted)
- Dichte
- 1.31 · 1.31±0.1 g/cm3(Predicted)
- pka
- 14.82 · 14.82±0.60(Predicted)
Chemie und Industrie
Anwendungen
BeschreibungThe leaves of Tabernanthe iboga and T. subsessilis yield this alkaloid which occurs with ibophyllidine (q.v.). When crystallized from Me2CO it yields colourless monoclinic crystals. The base has a specific rotation of [α]D + 444° (c 1.0, CHCl3) and gives an ultraviolet spectrum in EtOH with absorption maxima at 227, 295 and 328 nm. Iboxyphylline has been characterized as the O-acetate with m.p. 167°C and a specific rotation of [α]D + 466° (c 1.0, CHCI3). The structure given above has been confirmed by X-ray crystallography. The crystals are monoclinic with space group P2 1 and a = 9.7642, b = 12.4493 and c = 8.1182 A with Z = 2.
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