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CAS RN: 1678540-23-2 | 產品號碼: E1267
Ethyl (11bR)-4-Amino-2,6-bis(3,5-di-tert-butylphenyl)-4,5-dihydro-3H-cyclohepta[1,2-a:7,6-a']dinaphthalene-4-carboxylate
![Ethyl (11bR)-4-Amino-2,6-bis(3,5-di-tert-butylphenyl)-4,5-dihydro-3H-cyclohepta[1,2-a:7,6-a']dinaphthalene-4-carboxylate No-Image](/medias/E1267.jpg?context=bWFzdGVyfHJvb3R8NzE4MDJ8aW1hZ2UvanBlZ3xhREV6TDJnMVlTODRPVEl4TmpZek5qWTRNalUwTDBVeE1qWTNMbXB3Wnd8YTE2MGM4Y2FhYzFlMDNlYjEwYTk5NTg1NDYwOTc5ZmE1M2EwNDhiYTFiZjM5ZDlkY2VjYjE4ODM3MmM1OWJjYQ)
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產品號碼 | E1267 |
純度/分析方法 | >97.0%(HPLC) |
分子式 / 分子量 | C__5__4H__6__3NO__2 = 758.10 |
外觀與形狀(20°C) | Solid |
儲存條件 | Refrigerated (0-10°C) |
應避免的情況 | Heat Sensitive |
CAS RN | 1678540-23-2 |
PubChem Substance ID | 354334205 |
產品規格
Appearance | White to Almost white powder to crystal |
Purity(HPLC) | min. 97.0 area% |
NMR | confirm to structure |
性質
GHS
圖形表示 |
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信號詞 | Warning |
危險性說明 | H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
防範說明 | P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P302 + P352 : IF ON SKIN: Wash with plenty of water. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P362 + P364 : Take off contaminated clothing and wash it before reuse. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. |
相關法規
運輸資料
HS編碼* | 2922.49-000 |
Application
Decarboxylative Asymmetric Chlorination Using an Asymmetric Catalyst
Experimental procedure:
To a stirred solution of 1 (10 mol%), N-chlorosuccinimide (1.5 eq.) in toluene is added α-alkyl-β-ketocarboxylic acid (1 eq.) and the reaction mixture is stirred under darkness. After completion, the resulting mixture is subjected directly silica gel column chromatography (hexane:dichloromethane) to give the corresponding α-chloroketone.
To a stirred solution of 1 (10 mol%), N-chlorosuccinimide (1.5 eq.) in toluene is added α-alkyl-β-ketocarboxylic acid (1 eq.) and the reaction mixture is stirred under darkness. After completion, the resulting mixture is subjected directly silica gel column chromatography (hexane:dichloromethane) to give the corresponding α-chloroketone.
References
- Enantioselective decarboxylative chlorination of β-ketocarboxylic acids
Application
An Enantioselective Fluorination of α-Branched Aldehydes Using Newly Developed Chiral Amine Catalyst
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Typical Procedure (synthesis of 2-fluoro alcohol; Ar=Ph, R1=CH3):
To a solution of the chiral amine catalyst [E1267] (20 mg, 0.026 mmol, 10 mol%) in toluene (0.54 mL) is added 3,5-dinitrobenzoic acid (5.5 mg, 0.026 mmol, 10 mol%), 2-phenylpropionaldehyde (52 mg, 0.39 mmol, 1.5 eq.), and N-fluorobenzenesulfonimide (NFSI) (0.26 mmol, 82 mg, 1 eq.) at 0 °C. The reaction mixture is stirred at 0 °C for 48 h, then poured into CH3OH/CH2Cl2 (1:4, 1.3 mL) at 0 °C. To this solution, NaBH4 (1.6 mmol, 6 eq.) is added, and the mixture is stirred at room temperature for 1 h. The reaction is quenched with saturated aq.NH4Cl, and the mixture is extracted with Et2O. The organic layer is dried over Na2SO4, and concentrated. The residue is purified by silica gel chromatography (eluent: hexane/ethyl acetate = 3/1) to give (S)-2-fluoro-2-phenylpropan-1-ol (34.5 mg, 86% yield based on NFSI, 95% ee) as a white solid.
To a solution of the chiral amine catalyst [E1267] (20 mg, 0.026 mmol, 10 mol%) in toluene (0.54 mL) is added 3,5-dinitrobenzoic acid (5.5 mg, 0.026 mmol, 10 mol%), 2-phenylpropionaldehyde (52 mg, 0.39 mmol, 1.5 eq.), and N-fluorobenzenesulfonimide (NFSI) (0.26 mmol, 82 mg, 1 eq.) at 0 °C. The reaction mixture is stirred at 0 °C for 48 h, then poured into CH3OH/CH2Cl2 (1:4, 1.3 mL) at 0 °C. To this solution, NaBH4 (1.6 mmol, 6 eq.) is added, and the mixture is stirred at room temperature for 1 h. The reaction is quenched with saturated aq.NH4Cl, and the mixture is extracted with Et2O. The organic layer is dried over Na2SO4, and concentrated. The residue is purified by silica gel chromatography (eluent: hexane/ethyl acetate = 3/1) to give (S)-2-fluoro-2-phenylpropan-1-ol (34.5 mg, 86% yield based on NFSI, 95% ee) as a white solid.
References
考研文獻
文章/手冊
TCIMail
[Research Articles] Decarboxylative Asymmetric Chlorination Using an Asymmetric Catalyst[Research Articles] An Enantioselective Fluorination of α-Branched Aldehydes Using Newly Developed Chiral Amine Catalyst
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