(2S,4S)-10-hydroxy-11-methoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohex-2-ene]-1'-one
Grundinformationen
- CAS
10214-55-8- Standard-SMILES
COc1c(O)cc2c3c1[C@]1(C=CC(=O)CC1)C[C@@H]3N(C)CC2- InChIKey
QRZPTEFOIYHABZ-UGSOOPFHSA-N- Summenformel
- C18H21NO3
- Durchschnittliche Molmasse
- 299,4 g/mol
- Monoisotopische Masse
- 299,15214353
Namen und Bezeichner
- Bevorzugter Name
- (2S,4S)-10-hydroxy-11-methoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohex-2-ene]-1'-one
- IUPAC
- (2S,4S)-10-hydroxy-11-methoxy-5-methylspiro[5-azatricyclo[6.3.1.04,12]dodeca-1(12),8,10-triene-2,4'-cyclohex-2-ene]-1'-one
- Englischer Name
- (1S)-2',3',8',8'aβ-Tetrahydro-5'-hydroxy-6'-methoxy-1'-methylspiro[2-cyclohexene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-one
- Summenformel
- C18H21NO3
- Molmasse
- 299.36
Namen und Synonyme
Linearisine(1S)-2',3',8',8'aβ-Tetrahydro-5'-hydroxy-6'-methoxy-1'-methylspiro[2-cyclohexene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-oneSpiro[2-cyclohexene-1,7'(1'H)-cyclopent[ij]isoquinolin]-4-one, 2',3',8',8'a-tetrahydro-5'-hydroxy-6'-methoxy-1'-methyl-, (1S,8'aS)-
Datenbank-Bezeichner
- CAS
10214-55-8- PubChem CID
- 162877108
- Nikkaji
- J15.666C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2
- Polarare Oberfläche (TPSA)
- 49,8 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 505
Physikochemische Eigenschaften
- Schmelzpunkt
- 219 · 219-222°C
- Siedepunkt
- 444.6 · 444.6±45.0 °C(Predicted)
- Dichte
- 1.3 · 1.30±0.1 g/cm3(Predicted)
- pka
- 9.87 · 9.87±0.20(Predicted)
Chemie und Industrie
Anwendungen
BeschreibungThe empirical formula for this alkaloid from Croton linearis Jacq. was originally given as C 1 7H 1903N, representing it as a dihydrocrotonosine. This was later altered to that given above when it was shown that a methylimino group is present. The structure has now been confirmed as dihydro-N-methylcrotonosine. When crystallized from EtOH it forms anisotropic columns. The ultraviolet spectrum shows three absorption maxima at 228, 282 and 288 ffi/J. and the specific rotation in [o:Jf>8 + 116° (c 0.83, MeOH). The hydrochloride also forms colourless columnar crystals which decompose, without melting, above 300°C. One phenolic hydroxyl group is present and on methylation, the alkaloid yields Amuronine (q.v.).
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