5,5-ジメチル-1-ピロリンN-オキシド
5,5-ジメチル-1-ピロリンN-オキシド · 5,5-ジメチル-4,5-ジヒドロ-3H-ピロール1-オキシド · 3,4-ジヒドロ-2,2-ジメチル-2H-ピロール1-オキシド · 4,5-ジヒドロ-5,5-ジメチル-3H-ピロール1-オキシド · 5,5-ジメチル-3,4-ジヒドロ-5H-ピロール1-オキシド · 5,5-ジメチル-1-ピロリン-N-オキシド · 1-オキシラト-2,2-ジメチル-3,4-ジヒドロ-2H-ピロール-1-イウム · 3,4-ジヒドロ-1-オキシラト-2,2-ジメチル-2H-ピロリウム
識別子と物理属性
| CAS No. | 3317-61-1 |
|---|---|
| 分子式 | C6H11NO |
| 平均分子量 | 113.16 g/mol |
| 単同位体質量 | 113.08406397 g/mol |
| SMILES | CC1(C)CCC=[N+]1[O-] |
| InChIKey | VCUVETGKTILCLC-UHFFFAOYSA-N |
| PubChem CID | 1774 |
| ChEMBL | CHEMBL79824 |
| ChEBI | CHEBI:149489 |
| EC No. | 222-011-1 |
| DTXSID | DTXSID30186826 |
| 現地名 | 5,5-ジメチル-1-ピロリンN-オキシド |
化学・物理的性質
| XLogP | -0.3 |
|---|---|
| 極性表面積 | 28.8 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 126 |
| 物質分類 | Other Uses -> Biochemical Research |
| Physical Description | White solidHighly hygroscopic[Merck Index] Light yellow, hygroscopic solidified mass or fragmentsmp = 25-29 deg C[Sigma-Aldrich MSDS] |
| 融点 | 25-29 °C (lit.) |
| 沸点 | 75 °C/0.4 mmHg (lit.) |
| 密度 | 1.015 g/mL at 25 °C (lit.) |
| 屈折率 | n20/D 1.496(lit.) |
| 引火点 | 204 °F |
| 貯蔵条件 | -20°C |
| 溶解度 | DMSO (最大 25mg/ml) またはエタノール (最大 25mg/ml) に可溶。 |
| 外観・状態 | 淡黄色の固体または油。 |
| pKa（酸解離定数） | 2.47±0.40(Predicted) |
| 色 | ペールイエロー |
| Merck | 14,3393 |
| BRN | 107603 |
| 安定性 | 安定していますが、光、湿気、熱に弱いです。不活性ガス下の暗所に保管し、冷暗所に保管してください。強力な酸化剤、湿気とは相容れない。 |
| InChI | 1S/C6H11NO/c1-6(2)4-3-5-7(6)8/h5H,3-4H2,1-2H3 |
| InChIKey | VCUVETGKTILCLC-UHFFFAOYSA-N |
| SMILES | CC1(C)CCC=[N+]1[O-] |
| CAS データベース | 3317-61-1(CAS DataBase Reference) |
化学的特性
white to faintly yellow solid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.Not ClassifiedAggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| 有害性の概要 | May cause irritation[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Not Classified |
| F | 8-10 |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29339900 |
| 安全措置（S） | 24/25 |
| 危険等級 | IRRITANT |
| 貯蔵分類 | 10 - Combustible liquids |
用途
説明
Free radicals are highly reactive, short-lived species. Spin traps react with radicals, forming stable adducts that can be further studied. DMPO is a commonly-used spin trap that reacts with O-, N-, S-, and C-centered radicals. This allows their characterization when used in association with electron spin resonance and immuno-spin trapping. DMPO is water-soluble, rapidly penetrates lipid bilayers, has low toxicity, and can be used in vitro and in vivo.
使用
5,5-Dimethyl-1-pyrroline N-oxide is a reagent generally used either as a free-radical spin-trapping agent, or electrophilic component during the synthesis of pyrrolidine derivatives. It may also be considered as 1,3-dipole in cycloaddition processes.
製法・合成法
製造方法
To a three-necked round bottom flask equipped with a condenser, addition funnel, thermometer, and mechanical stirrer and containing 300 ml. 95% ethanol precooled to 2°C is added, all at once, 14.5 g (0.1 mole) 4-methyl-4-nitropentanol, and 13.1 g (1.2 mole) zinc dust. With rapid agitation, the glacial acetic acid (24.0 g, 0.4 mole) is added dropwise over a 1-hr period while maintaining the reaction temperature below 15°C. The mixture is stirred vigorously for 2 hr and then stored in the refrigerator for 2 days, at approximately 1°C. Then the zinc acetate is filtered and rinsed with 100 ml of ethanol. The combined ethanol factions are rotoevapo-rated to give the crude nitrone. The crude nitrone is dissolved in a 200 ml portion of dichloromethane and the latter washed two times with saturated sodium bicarbonate solution. The organic layer is dried over sodium sulfate and the solvent rotoevaporated, to give 10.7 (94% yield) of the crude nitrone. The product was purified by double distillation (b.p. 53°C, 0.1 Torr), to give 6.8 g (60%) of the pure nitrone as a white hygroscopic solid. The H1 NMR (400 MH CDC13, Me4Si) is 6.80 (t, 2H, methylene bound to quaternary C, J = 7.2Hg), 1.43 (s, 6H, methyl), C13NMr (100 MH2, CDC13, Me4 Si) 5=132.4 (Vinyl), 73.5 (quaternary), 34.1 (Allyl), 25.3 (methylene bound to quaternary C), 24.4 (methyls).