Structure of 889-31-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 889-31-6 |
Formula : | C15H19NO |
M.W : | 229.32 |
SMILES Code : | CC(C1)(C)CC(NCC2=CC=CC=C2)=CC1=O |
MDL No. : | MFCD00170309 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | at 90℃; for 15h;Neat (no solvent); | Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | at 90℃; for 14h;Neat (no solvent); | Aldehyde 1 (1 mmol), dihydrothiophen-3(2H)-one-1,1-dioxide 2 (0.134 g, 1 mmol), enaminone 3 (1 mmol) and were triturated together in an agate mortar for 5 minutes. Then the mixture was kept at 90 C for a certain time (monitored by TLC). The result mixture was washed with water and recrystallized from ethanol (95 %) to give pure product 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), benzyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/petroleum ether (60-80 C)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), benzyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/petroleum ether (60-80 C)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), benzyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/petroleum ether (60-80 C)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), benzyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/petroleum ether (60-80 C)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), benzyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/petroleum ether (60-80 C)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), aryl or alkyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/ petroleum ether (60-80 C)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tert.-butylhydroperoxide; copper diacetate; In water; at 30℃; for 12h; | General procedure: A mixture of N-benzyl enaminoketone (1.0 mmol), di-alkylacetylenedicarboxylate (1.0 mmol), aryl or alkyl amine (1.0 mmol), Cu(OAc)2 (8 mol%) and TBHP (4.0 mmol, 0.56 mL of a 70% aqueous solution) in water (0.5 mL) was stirred at 30 C for 12 h under air. The reaction progress was monitored by TLC. After completion of the reaction, the solid was filtrated out and washed with hot ethyl acetate. Finally the solvent of the filtrate was removed under vacuum and the resulting crude product was purified by column chromatography over 60-120 mesh silica gel [ethyl acetate/ petroleum ether (60-80 C)]. |