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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.
7-Ethoxycoumarin is a substrate for cytochrome P450 (CYP450) used for the functional characterization of various CYPs.
Synonyms: 7-O-Ethylumbelliferone
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| CAS No. : | 31005-02-4 |
| Formula : | C11H10O3 |
| M.W : | 190.20 |
| SMILES Code : | O=C1OC2=C(C=CC(OCC)=C2)C=C1 |
| Synonyms : |
7-O-Ethylumbelliferone
|
| English Name : | 7-Ethoxy-2H-chromen-2-one |
| MDL No. : | MFCD00006877 |
| InChI Key : | LIFAQMGORKPVDH-UHFFFAOYSA-N |
| Pubchem ID : | 35703 |
* 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% | Stage #1: 7-hydroxy-2H-chromen-2-one With potassium carbonate In acetone for 0.5h; Stage #2: ethyl iodide With potassium iodide In acetone at 40℃; for 60h; | 4.1.3 Preparation ,of 2, 8 and 14 (Scheme 1b) General procedure: 0.4g of SM1 (2.2mmol), SM2 (2.4mmol) and SM3 (2.2mmol), respectively, were dissolved with 2mL of DMF (compound 2) or acetone (compound 8 and 14). After that, solid K2CO3 (1.9 or 3.8 equivalents) were add, and stirred during thirty minutes. 2.2 equivalents of ethyl iodide and potassium iodide (as catalyst) were added to the mixture and heating for 2, 2.5 and 5 days at 40°C, respectively. Finally, when reaction was completed (monitored by TLC analysis), the solid was filtered off and dried to afford the corresponding compounds 2 (6,7-diethoxy-2H-chromen-2-one), 8 (7-ethoxy-2H-chromen-2-one) and 14 (7-ethoxy-4-methyl-2H-chromen-2-one). |
| With potassium carbonate; acetone | ||
| With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With liver cytochrome P450 IA2 (wild type) at 25℃; catalytic efficiency in the presence of P450 IA2 mutants; also hydroxylation of methanol at the same conditions; | ||
| With fusion enzyme between rat P4501A1 and yeast P450 reductase from microsomal fraction of recombinant yeast AH22; NADPH In water at 30℃; effect of phosphatidylcholin; | ||
| With rat hepatocytes In various solvent(s) at 37℃; for 0.3h; |
| With 1,1,2,2-tetrachloroethylene; rat hepatic microsome | ||
| With Arachidonic acid; NADPH-generating system; recombinant human cytochrome P450 or CYP enzymes In phosphate buffer Enzymatic reaction; | ||
| With Lentinula edodes (Le.) cytochrome P450 CYP1 | ||
| With mutant Q87W T115A H132L R191W G294D actinomycete cytochrome P450; water at 28℃; for 4h; aq. phosphate buffer; Enzymatic reaction; | ||
| With cytochrome Noc4(nfa46410)-RhFRed-expressing Escherichia coli Rosetta 2 strain at 4℃; for 72h; Enzymatic reaction; | ||
| With cytochrome P450 2A6 variant; glycerol In aq. phosphate buffer; glycerol at 37℃; for 0.5h; Darkness; Enzymatic reaction; | ||
| With D-glucose; GDH; cytochrome P450 monooxygenase CYP116B4 from Labrenzia aggregata; nicotinamide adenine dinucleotide phosphate In aq. buffer at 30℃; for 5h; Enzymatic reaction; | ||
| With NADPH; cytochrome P450 monooxygenase from Labrenzia aggregata In aq. buffer at 30℃; for 5h; Enzymatic reaction; | ||
| With feline cytochrome P450 2A13 isoform In aq. phosphate buffer at 37℃; for 0.0833333h; Enzymatic reaction; | ||
| With NADPH; cytochrome P450 BM3 Electrochemical reaction; Enzymatic reaction; | ||
| With recombinant marmoset P450 2F1 | ||
| With cytochrome P450 monooxygenase from Labrenzia aggregata In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 4h; Enzymatic reaction; | ||
| With cytochrome P450 monooxygenase Enzymatic reaction; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium hydroxide In ethanol; water at 20℃; Schotten-Baumann reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 67% | With Lawessons reagent In toluene at 110℃; for 24h; | |
| 65% | With Lawessons reagent In toluene for 12h; Reflux; | Preparation of 7-ethoxythiocoumarin 2 Lawesson’s reagent (0.44 g, 1.1 mmol) wasadded to a solution of 7-ethoxycoumarin (0.19 g, 1.0 mmol) in toluene (15 mL). Themixture was refluxed for 12 h and cooled to room temperature. The organic solvent wasremoved under reduced pressure. The residue was purified by column chromatography(silica gel 240 mesh, 1st eluent: dichloromethane, 2nd eluent: ethyl acetate-hexane = 3:1,v/v) to yield thiocoumarin 2 (0.13 g, 65%). 1H NMR (600 MHz, CDCl3) δ 7.37 (m, 2H),7.05 (d, J = 9.2 Hz, 1H), 6.89 (d, J = 2.4 Hz, 1H), 6.85 (dd, J = 8.6 and 2.4 Hz, 1H), 4.06(q, J = 7.0 Hz, 2H), 1.43 (t, J = 7.0 Hz, 3H); 13C NMR (150 MHz, CDCl3) δ 197.8, 162.7,158.5, 135.1, 128.7, 126.6, 114.7, 114.2, 100.8, 64.2, 14.5; HRMS (FAB); m/z calcd forC11H10O2S [M]+: 206.0402, found 206.0388. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 74% | Stage #1: 7-ethoxycoumarin With 1,10-Phenanthroline; oxygen; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Stage #2: phenylboronic acid In N,N-dimethyl-formamide at 100℃; for 24h; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate In N,N-dimethyl-formamide at 55 - 85℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 74% | With palladium(II) trimethylacetate; oxygen; potassium carbonate; Trimethylacetic acid at 100℃; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | With copper(II) acetate monohydrate; palladium dichloride In 1,4-dioxane at 80℃; for 24h; Molecular sieve; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 61% | With copper dichloride; palladium dichloride In 1,4-dioxane at 100℃; for 24h; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91% | With palladium diacetate; trifluoroacetic anhydride at 120℃; for 16h; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 62% | With [2,2]bipyridinyl; dipotassium peroxodisulfate; palladium dichloride In acetonitrile at 100℃; for 24h; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 67% | With [2,2]bipyridinyl; dipotassium peroxodisulfate; palladium dichloride In acetonitrile at 100℃; for 5h; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | With 1,10-Phenanthroline; palladium diacetate; silver carbonate In dimethyl sulfoxide at 130℃; for 72h; Sealed tube; regioselective reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | With 1,10-Phenanthroline; palladium diacetate; silver carbonate In dimethyl sulfoxide at 130℃; for 72h; Sealed tube; regioselective reaction; |