(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trione
Grundinformationen
- CAS
110351-94-5- Standard-SMILES
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)CCC1=O- InChIKey
IGKWOGMVAOYVSJ-ZDUSSCGKSA-N- Summenformel
- C13H13NO5
- Durchschnittliche Molmasse
- 263,25 g/mol
- Monoisotopische Masse
- 263,07937252
Namen und Bezeichner
- Bevorzugter Name
- (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trione
- IUPAC
- (4S)-4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10-trione
- Englischer Name
- (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione
- Summenformel
- C13H13NO5
- Molmasse
- 263.25
Namen und Synonyme
(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano(3,4-f)indolizine-3,6,10(4H)-trioneRefChem:403426828-521-6110351-94-5(S)-4-ETHYL-4-HYDROXY-7,8-DIHYDRO-1H-PYRANO[3,4-F]INDOLIZINE-3,6,10(4H)-TRIONE(4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10-trioneExatecan Intermediate 1MFCD09833229IGKWOGMVAOYVSJ-ZDUSSCGKSA-N1H-Pyrano[3,4-f]indolizine-3,6,10(4H)-trione, 4-ethyl-7,8-dihydro-4-hydroxy-, (4S)-YZ4S6C3GB5
Weitere Namen anzeigen
(S)-trione(S)-4-hydroxy-4-propyl-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trioneRUBI-00610(4H)-TRIONE4-F]INDOLIZINE-3Trihydroxy lactoneExatecan Impurity 38-DIHYDRO-1H-PYRANO[3
SCHEMBL614060R-tetrahydropapaverine bitartrateDTXSID30436954CS-B1681EX-A4321AKOS005145923FE23128(4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,8
- Polarare Oberfläche (TPSA)
- 83,9 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 574
Physikochemische Eigenschaften
- Schmelzpunkt
- 183 · 183-185℃ (decomposition)
- Siedepunkt
- 666.6 · 666.6±55.0 °C(Predicted)
- Dichte
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 11.2 · 11.20±0.20(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Off-white to light brown
- InChI
- InChI=1S/C13H13NO5/c1-2-13(18)8-5-9-10(15)3-4-14(9)11(16)7(8)6-19-12(13)17/h5,18H,2-4,6H2,1H3/t13-/m0/s1
- InChIKey
- IGKWOGMVAOYVSJ-ZDUSSCGKSA-N
- SMILES
- C1(=O)C2N(C(=O)C3COC(=O)[C@@](CC)(O)C=3C=2)CC1
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- hazard_class
- IRRITANT
Chemie und Industrie
Anwendungen
Verwenden(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione is a key intermediate in the synthesis of Irinotecan (I767500) and Camptothecin (C175150) analogs.
Darstellung
synthetischeSynthesis of (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione: Compound (Formula 4) 4.3 g (100 mmol), 200 ml of dichloromethane, 200 ml of 2M sulfuric acid, stirred at room temperature for 2 h, separated the organic layer, washed with saturated brine, dried, recovered dichloromethane to dryness, and recrystallized from isopropanol to obtain S-tricyclic lactone (Formula 1) 1.5 g, mp 172-174°C, [α]D15+115.6° (C=0.5, chloroform), yield 57%.
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