Tropinon
Tropanone · 8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-ONE · Tropinon · 3-Tropinone · (1R,5S)-8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-ONE · Tropanon · ropinone · TROPINONE
Identifikatoren & physikalische Daten
| CAS No. | 532-24-1 |
|---|---|
| Summenformel | C8H13NO |
| Durchschnittliche Molmasse | 139,19 g/mol |
| SMILES | CN1[C@@H]2CC[C@H]1CC(=O)C2 |
| InChIKey | QQXLDOJGLXJCSE-KNVOCYPGSA-N |
| PubChem CID | 446337 |
| ChEMBL | CHEMBL1236344 |
| ChEBI | CHEBI:16656 |
| EC No. | 208-530-6 |
| Lokaler Name | Tropinon |
Chemische & physikalische Eigenschaften
| XLogP | 0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 151 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Chemical shift |
| Schmelzpunkt | 40-44 °C(lit.) |
| Siedepunkt | 113 °C25 mm Hg(lit.) |
| Dichte | 1.0268 (rough estimate) |
| Brechungsindex | 1.4598 (estimate) |
| Flammpunkt | 194 °F |
| Lagerbedingungen | Inert atmosphere,2-8°C |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly) |
| pKa (Säurekonstante) | 8.93±0.20(Predicted) |
| Aggregatzustand | crystalline |
| Farbe | brown |
| pH | 8 (18g/l, H2O, 20℃) |
| BRN | 2329 |
| InChI | 1S/C8H13NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-7H,2-5H2,1H3/t6-,7+ |
| InChIKey | QQXLDOJGLXJCSE-KNVOCYPGSA-N |
| SMILES | CN1[C@@H]2CC[C@H]1CC(=O)C2 |
| CAS Datenbank | 532-24-1(CAS DataBase Reference) |
| NIST chemische Informationen | 8-Azabicyclo[3.2.1]octan-3-one, 8-methyl-(532-24-1) |
| EPA chemische Informationen | 8-Azabicyclo[3.2.1]octan-3-one, 8-methyl- (532-24-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302+H332 (11.1%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation]P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 9 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 1544 |
| Zollcode | 29399990 |
| R-Sätze (R) | 34-22-36/37/38 |
| Gefahrensymbole | C,Xi |
| Sicherheitshinweise (S) | 23-24/25-36/37/39-26-22 |
| Gefahrenklasse | 6.1Acute Tox. 4 InhalationAcute Tox. 4 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Tropinone (8-methyl-8-azabicyclo[3.2.1]octane-3-one)(7) is the simplest plant tropane and is the first intermediate in the biosynthesis of tropane alkaloids. Studies have called 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoic acid as an intermediate metabolite in tropinone biosynthesis[1]. It is an intermediate of atropine sulfate and is used in the synthesis of atropine. Atropine is an anticholinergic drug. It acts as an M-blocker and is indicated for the relief of visceral colic.
Verwenden
Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids.
Herstellung & Synthese
synthetische
The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine. The 1917 synthesis by Robinson is considered a legend in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methyl amine and acetone dicarboxylic acid (or even acetone). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis. Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%.