トロピノン
トロピノン · 1-メチル-2,6-エタノピペリジン-4-オン · 8-メチル-8-アザビシクロ[3.2.1]オクタン-3-オン · トロパン-3-オン · 8-メチル-3,6-エピミノシクロヘプタン-1-オン · 3-トロパノン · トロピノン, 99% · Tropanone
識別子と物理属性
| CAS No. | 532-24-1 |
|---|---|
| 分子式 | C8H13NO |
| 平均分子量 | 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 |
| 現地名 | トロピノン |
化学・物理的性質
| XLogP | 0.3 |
|---|---|
| 極性表面積 | 20.3 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 151 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Chemical shift |
| 融点 | 40-44 °C(lit.) |
| 沸点 | 113 °C25 mm Hg(lit.) |
| 密度 | 1.0268 (rough estimate) |
| 屈折率 | 1.4598 (estimate) |
| 引火点 | 194 °F |
| 貯蔵条件 | Inert atmosphere,2-8°C |
| 溶解度 | クロロホルム（微量）、メタノール（微量） |
| pKa（酸解離定数） | 8.93±0.20(Predicted) |
| 外観・状態 | 結晶性 |
| 色 | 茶色 |
| 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 データベース | 532-24-1(CAS DataBase Reference) |
| NISTの化学物質情報 | 8-Azabicyclo[3.2.1]octan-3-one, 8-methyl-(532-24-1) |
| EPAの化学物質情報 | 8-Azabicyclo[3.2.1]octan-3-one, 8-methyl- (532-24-1) |
化学的特性
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.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | 1544 |
| 税関コード | 29399990 |
| 危険文句（R） | 34-22-36/37/38 |
| 危険表示 | C,Xi |
| 安全措置（S） | 23-24/25-36/37/39-26-22 |
| 危険等級 | 6.1Acute Tox. 4 InhalationAcute Tox. 4 Oral |
| 包装等級 | III |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
トロピノン(Tropinone)は、第一次世界大戦の際に不足したアトロピンの前駆体として1917年にロバート・ロビンソンによって合成されたのが有名なアルカロイドである。トロピノン、コカイン及びアトロピンは、全て同じトロパン骨格を持っている。
説明
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.
使用
Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids.
製法・合成法
製造方法
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%.