Tropinone
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
식별자 및 물리적 특성
| CAS No. | 532-24-1 |
|---|---|
| 분자식 | C8H13NO |
| 평균 분자량 | 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 |
화학 및 물리적 성질
| XLogP | 0.3 |
|---|---|
| 극성 표면적 | 20.3 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 10 |
| 형식 전하 | 0 |
| 복잡도 | 151 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Chemical shift |
| 녹는점 | 40-44 °C(lit.) |
| 끓는 점 | 113 °C25 mm Hg(lit.) |
| 밀도 | 1.0268 (rough estimate) |
| 굴절률 | 1.4598 (estimate) |
| 인화점 | 194 °F |
| 저장 조건 | Inert atmosphere,2-8°C |
| 용해도 | 클로로포름(약간 용해됨), 메탄올(약간 용해됨) |
| pKa(산도 계수) | 8.93±0.20(Predicted) |
| 물리적 상태 | 수정 같은 |
| 색상 | 갈색 |
| 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 |
| NIST | 8-Azabicyclo[3.2.1]octan-3-one, 8-methyl-(532-24-1) |
| EPA | 8-Azabicyclo[3.2.1]octan-3-one, 8-methyl- (532-24-1) |
화학적 성질
Tropinone is a white to light yellow crystal powder, It is an alkaloid and a precursor to a number of additional plant alkaloids. Tropinone is the first intermediate in the biosynthesis of the pharmacologically important tropane alkaloids that possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Chemical synthesis of tropinone was achieved in 1901 but the mechanism of tropinone biosynthesis has remained elusive.
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| 운송 번호(UN) | 1544 |
| 관세 코드 | 29399990 |
| 위험 문구(R) | 34-22-36/37/38 |
| 위험 표시 | C,Xi |
| 안전 문구(S) | 23-24/25-36/37/39-26-22 |
| 포장분류 | III |
| 위험 등급 | 6.1Acute Tox. 4 InhalationAcute Tox. 4 Oral |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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.
용도
Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids.
제조 및 합성 방법
제조 방법
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%.