3-イソクロマノン
3-イソクロマノン · イソクロマン-3-オン · 1,4-ジヒドロ-3H-2-ベンゾピラン-3-オン · 1H-2-ベンゾピラン-3(4H)-オン · 3,4-ジヒドロ-1H-2-ベンゾピラン-3-オン · 3‐イソクロマノン · ISOCHROMAN-3-ONE · 3- Isochromone
識別子と物理属性
| CAS No. | 4385-35-7 |
|---|---|
| 分子式 | C9H8O2 |
| 平均分子量 | 148.16 g/mol |
| 単同位体質量 | 148.0524295 g/mol |
| SMILES | O=C1Cc2ccccc2CO1 |
| InChIKey | ILHLUZUMRJQEAH-UHFFFAOYSA-N |
| PubChem CID | 78092 |
| ChEMBL | CHEMBL447815 |
| EC No. | 224-493-9 |
| DTXSID | DTXSID00195960 |
| 現地名 | 3-イソクロマノン |
化学・物理的性質
| XLogP | 1.3 |
|---|---|
| 極性表面積 | 26.3 |
| 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 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 165 |
| LogP（分配係数） | 1.02 |
| 融点 | 80-82 °C (lit.) |
| 沸点 | 130 °C / 1mmHg |
| 密度 | 1.196±0.06 g/cm3(Predicted) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 溶解度 | クロロホルム（微量、加熱、超音波処理）、メタノール（微量） |
| 外観・状態 | 個体 |
| 色 | ホワイト～ペールベージュ |
| BRN | 123692 |
| InChI | InChI=1S/C9H8O2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-4H,5-6H2 |
| InChIKey | ILHLUZUMRJQEAH-UHFFFAOYSA-N |
| SMILES | C1(=O)OCC2=CC=CC=C2C1 |
| CAS データベース | 4385-35-7(CAS DataBase Reference) |
化学的特性
Lamellae
安全性と法規制
| GHS 分類 | WarningH315 (67.1%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 85 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (67.1%) |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 2932990090 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (5)-6813 |
| 危険表示 | Xi |
| 安全措置（S） | 26-37/39 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
使用
3-Isochromanone may be used as starting reagent in the synthesis of of BDPBI (7-bromo-1,4-dihydro-2-phenyl-4,4-bis(4-pyridinylmethyl)2H-isoquinolin-3-one dihydrochloride).
一般的な説明
3-Isochromanone has been reported to be isolated from the fungus Nigrospora sp. PSU-F12. An improved Knoevenagel condensation of 3-isochromanone with aromatic aldehydes has been achieved by microwave irradiation on solid supports in the presence of various catalysts. Synthesis of 3-isochromanone via Beayer-Villiger rearrangement has been reported.
製法・合成法
調製方法
3-Isochromanone is a well-known compound, and several methods for its preparation are described in the chemical literature. For example, it can be prepared by (i) the Baeyer-Villiger oxidation of 2-indanone using hydrogen peroxide in sulphuric acid and acetic anhydride or using 3-chloroperoxybenzoic acid combined with trifluoroacetic acid; (ii) from 2-methoxycarbonylmethylbenzoic acid by (a) treatment with ethyl chloroformate in triethylamine and (b) sodium borohydride; or (iii) from isochroman-3-ol and chromium trioxide. It is also known to prepare 3-isochromanone by the bromination of o-tolylacetic acid with N-bromosuccinimide followed by ring closure by boiling the 2-bromomethylphenylacetic acid so formed with potassium hydroxide in ethanol.