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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.
Synonyms: Anthracen-9(10H)-one
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Search for reports by entering the product batch number.
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'.
Search for reports by entering the product batch number.
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'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 90-44-8 |
Formula : | C14H10O |
M.W : | 194.23 |
SMILES Code : | O=C1C2=C(C=CC=C2)CC3=CC=CC=C13 |
Synonyms : |
Anthracen-9(10H)-one
|
MDL No. : | MFCD00001187 |
InChI Key : | RJGDLRCDCYRQOQ-UHFFFAOYSA-N |
Pubchem ID : | 7018 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
93% | First, 9-anthrone (5 g, 26 mmol), zinc powder (8.5 g, 129 mmol), zinc chloride (7 g, 56 mmol) were added to a three-necked flask, and a certain percentage of 100 ml of a mixed solvent of tetrahydrofuran and water was added. The magnet was stirred for more than 8 hours at room temperature, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, spin-dried and dried to give 4.8 g of a yellow solid. The yellow solid was added to the three-necked flask and a small amount of p-toluenesulfonic acid was added. (PTS) using toluene as solvent, refluxing until the solvent becomes clear, extracting with solvent dichloromethane, drying with anhydrous magnesium sulfate as a drying agent, filtering, spin-drying, and purifying by silica gel column to obtain white crystalline solid 4.3 g, yield 93%. | |
With hydrogenchloride; tin; In acetic acid; | Example 1 Preparation of 1:1 [9,9']Bianthracenyl/Toluene adduct Anthrone (40.00 g, 206 mmol) was refluxed in a mixture of glacial acetic acid (200 ml) and concentrated hydrochloric acid (80 ml). To this refluxing solution granulated tin (80 g, 674 mmol) was cautiously added. The reaction was refluxed for 15 h during which time a white precipitate formed. The mixture was cooled to room temperature and the solution was carefully filtered under vacuum to isolate the precipitate but left unreacted in the reaction vessel. The precipitate was washed with water (100 ml) and dried in a vacuum oven. This solid was then recrystallized from the minimum amount of hot toluene (approximately 500 ml) to yield light yellow crystals of the 1:1 [9,9']Bianthracenyl/Toluene adduct (37 g, 81% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In toluene; at 20℃; for 14h; | General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature. | |
With (1R,2R)-N,N-dimethyl-N'-phthaloyl-1,2-diaminocyclohexane; In 1,2-dichloro-ethane; at -10℃; for 12h; | General procedure: A mixture of maleimide 3 (0.24 mmol), anthrone 2 (0.2 mmol), and the catalyst (20 mol %) in 1,2-dichloroethane (0.6 mL) at -10 C was stirred for 12 h (monitored by TLC). After evaporation under reduced pressure, the residue was purified through column chromatography on silica gel (petroleum ether/ethyl acetate=3/1) to yield pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | General procedure: All reactions were run in closed 50 mL polyethylene vessels. To a solution of anthrone (0.15-0.60 mmol) in CH2Cl2or other solvents (abs., 8 mL) at -40 C, the catalyst 10 (0.1 equiv) was added. After stirring for 15 minutes, maleimide was added to the mixture in one portion. The solution was allowed to warm up to -15 C overnight and stirred for two more days at this temperature. After warming up to room temperature the reaction mixture was purified by flash column chromatography (c-hexane/EtOAc 10:1) to afford the different products as crystalline solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium perchlorate; triethylamine; In chloroform; at 20℃; for 168h; | General procedure: All reactions were run in closed 50 mL polyethylene vessels. To a solution of anthrone (0.15-0.60 mmol) in CH2Cl2or other solvents (abs., 8 mL) at -40 C, the catalyst 10 (0.1 equiv) was added. After stirring for 15 minutes, maleimide was added to the mixture in one portion. The solution was allowed to warm up to -15 C overnight and stirred for two more days at this temperature. After warming up to room temperature the reaction mixture was purified by flash column chromatography (c-hexane/EtOAc 10:1) to afford the different products as crystalline solids. The racemic Diels-Alder products rac-25-rac-27 were prepared with triethylamine (1.0 equiv) instead of guanidine 10. After stirring for 24 hours at room temperature the reaction mixture was also purified by flash column chromatography (c-hexane/EtOAc 10:1).The racemic retro-aldol products rac-28-rac-31 were prepared with triethylamine (1.0 equiv.) instead of guanidine in the presence of a small amount of LiClO4acting as Lewis acid. After stirring for 7 days at room temperature the reaction mixture was also purified by flash column chromatography (c-hexane/EtOAc 10:1). |