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CAS RN: 903571-02-8 | Product Number: D3983
(+)-(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Monohydrate
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![(+)-(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Monohydrate](/_ui/responsive/theme-tci/images/missing_product_zoom.jpg "(+)-(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Monohydrate")
Purity: >98.0%(HPLC)
Synonyms:
- (+)-(5aR,10bS)-5a,10b-Dihydro-2-mesityl-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Monohydrate
- Bode Catalyst 2 Monohydrate
Product Documents:
| Size | Unit Price | Belgium | Japan* |
|---|---|---|---|
| 100MG |
€238.00
|
4 | 24 |
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | D3983 |
| Purity / Analysis Method | >98.0%(HPLC) |
| Molecular Formula / Molecular Weight | C__2__1H__2__2ClN__3O·H__2O = 385.90 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| CAS RN | 903571-02-8 |
| Reaxys Registry Number | 10505362 |
| PubChem Substance ID | 125307585 |
| MDL Number | MFCD10566989 |
Specifications
| Appearance | White to Gray to Red powder to crystal |
| Purity(HPLC) | min. 98.0 area% |
| Elemental analysis(Nitrogen) | 10.40 to 11.20 % |
| Specific rotation [a]20/D | +155 to +163 deg(C=1, CHCl3) |
Properties (reference)
| Melting Point | 219 °C |
| Specific Rotation | 158° (C=1,CHCl3) |
GHS
Related Laws:
Transport Information:
| HS Number | 2934999090 |
Application
Highly Enantioselective Diels-Alder Reactions using Bode 2 Catalyst
References
- 1)M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 8418.
- 2)M. He, G. J. Uc, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 15088.
- 3)J. R. Struble, J. W. Bode, Y. Lian, H. M. L. Davies, Org. Synth. 2010, 87, 362.
Application
[4+2] Cycloaddition of α,β-Unsaturated Aldehydes with Chalcones Using NHC (Bode Catalyst 2) and Acid Co-catalyst
Typical procedure (entry 1):
A dry 10 mL Schlenk tube is successively charged with 4-methoxycinnamaldehyde (81 mg, 0.5 mmol), chalcone (52 mg, 0.25 mmol), Bode catalyst 2 monohydrate (18.4 mg, 0.05 mmol), KOAc (61.4 mg, 0.625 mmol) and MS4Å (100 mg). The tube is closed with a septum, evacuated, and refilled with nitrogen. To this mixture is added distilled THF (0.5 mL), followed by AcOH (7.2 µL, 0.0625 mmol). The reaction mixture is stirred at room temperature for 24 h. After the reaction is completed, the solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: hexane/ethyl acetate = 10/1) to afford the corresponding lactone (79.6 mg, 86% yield, 20:1 dr, 99% ee) as a white solid.
A dry 10 mL Schlenk tube is successively charged with 4-methoxycinnamaldehyde (81 mg, 0.5 mmol), chalcone (52 mg, 0.25 mmol), Bode catalyst 2 monohydrate (18.4 mg, 0.05 mmol), KOAc (61.4 mg, 0.625 mmol) and MS4Å (100 mg). The tube is closed with a septum, evacuated, and refilled with nitrogen. To this mixture is added distilled THF (0.5 mL), followed by AcOH (7.2 µL, 0.0625 mmol). The reaction mixture is stirred at room temperature for 24 h. After the reaction is completed, the solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: hexane/ethyl acetate = 10/1) to afford the corresponding lactone (79.6 mg, 86% yield, 20:1 dr, 99% ee) as a white solid.
References
PubMed Literature
Articles/Brochures
TCIMAIL
[TCIMAIL No.150] Useful N-Heterocyclic Carbene Precatalysts “Bode Catalysts”[Research Articles] [4+2] Cycloaddition of α,β-Unsaturated Aldehydes with Chalcones Using NHC (Bode Catalyst 2) and Acid Co-catalyst
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