(S)-(-)-α,α-ジフェニル-2-ピロリジンメタノール
(S)-(-)-α,α-ジフェニル-2-ピロリジンメタノール · α-[(S)-2-ピロリジニル]-α-フェニルベンゼンメタノール · (2S)-2α-(ヒドロキシジフェニルメチル)ピロリジン · (2S)-α,α-ジフェニルピロリジン-2α-メタノール · (S)-ピロリジン-2-イルジフェニルメタノール · (S)-α,α-ジフェニル-2-ピロリジンメタノール · (S)-α,α-ジフェニル-2α-ピロリジンメタノール · [(2S)-2-ピロリジニル]ジフェニルメタノール
識別子と物理属性
| CAS No. | 112068-01-6 |
|---|---|
| 分子式 | C17H19NO |
| 平均分子量 | 253.34 g/mol |
| 単同位体質量 | 253.14666423 g/mol |
| SMILES | OC(c1ccccc1)(c1ccccc1)[C@@H]1CCCN1 |
| InChIKey | OGCGXUGBDJGFFY-INIZCTEOSA-N |
| PubChem CID | 2724899 |
| EC No. | 601-153-1 |
| DTXSID | DTXSID50369275 |
| 現地名 | (S)-(-)-α,α-ジフェニル-2-ピロリジンメタノール |
化学・物理的性質
| XLogP | 2.7 |
|---|---|
| 極性表面積 | 32.3 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 3 |
| 重原子数 | 19 |
| 形式電荷 | 0 |
| 複雑度 | 261 |
| 融点 | 77-80 °C(lit.) |
| 比旋光度 | -59 º (c=3, methanol 25 ºC) |
| 沸点 | 396.54°C (rough estimate) |
| 密度 | 1.0078 (rough estimate) |
| 屈折率 | -66.5 ° (C=3, CHCl3) |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 溶解度 | クロロホルムに可溶。 |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 13.15±0.29(Predicted) |
| 色 | ホワイトからオフホワイト、クリスタル |
| Merck | 14,155 |
| BRN | 17103 |
| InChI | 1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m0/s1 |
| InChIKey | OGCGXUGBDJGFFY-INIZCTEOSA-N |
| SMILES | OC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3 |
| CAS データベース | 112068-01-6(CAS DataBase Reference) |
| NISTの化学物質情報 | S-(-)-1,1-diphenylprolinol(112068-01-6) |
化学的特性
white to beige crystals or crystalline powder
安全性と法規制
| GHS 分類 | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (95.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract 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 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (95.7%) |
| F | 10-34 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | No |
| 税関コード | 29339900 |
| 危険文句（R） | 36/37/38 |
| 危険表示 | Xi |
| 安全措置（S） | 26-37/39-24/25-36 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
使用
suzuki reaction
一般的な説明
(S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol is a bifunctional organocatalyst.
製法・合成法
製造方法
Into a four-necked flask, add tetrahydrofuran, L-proline methyl ester hydrochloride, and phenyl magnesium chloride （dissolved in tetrahydrofuran) solution was added dropwise from a constant pressure dropping funnel, and the addition was completed in about 4 hours, and then stirred at 10-15°C for 3 hours. Add water, adjust the pH to 5-6 with 10% ammonium chloride aqueous solution, extract with dichloromethane, extract the aqueous layer twice with dichloromethane each time, and obtain the organic phase. Wash once with saturated sodium chloride aqueous solution. The organic phase was dried with anhydrous sodium sulfate for 4 hours and filtered. The obtained organic phase was distilled under reduced pressure to distill dichloromethane and tetrahydrofuran to obtain light yellow oily (S)-(-)-α,α-Diphenyl-2-pyrrolidinemethanol, yield 86.6%.