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CAS No. : | 1076-38-6 | MDL No. : | MFCD00006856 |
Formula : | C9H6O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VXIXUWQIVKSKSA-UHFFFAOYSA-N |
M.W : | 162.14 | Pubchem ID : | 54682930 |
Synonyms : |
Benzotetronic Acid;NSC 11889;4-Coumarinol
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 44.51 |
TPSA : | 50.44 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.39 cm/s |
Log Po/w (iLOGP) : | 1.36 |
Log Po/w (XLOGP3) : | 1.27 |
Log Po/w (WLOGP) : | 1.5 |
Log Po/w (MLOGP) : | 1.04 |
Log Po/w (SILICOS-IT) : | 1.97 |
Consensus Log Po/w : | 1.43 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.26 |
Solubility : | 0.887 mg/ml ; 0.00547 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.93 |
Solubility : | 1.91 mg/ml ; 0.0118 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.03 |
Solubility : | 0.153 mg/ml ; 0.000942 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.63 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
50% | With sodium hydroxide In benzene | STR39 Method C--Option 1 (Method "C-1") To a stirred mixture of sodium hydride (3.0 equiv., washed free of mineral oil) and diethyl carbonate (10.0 equiv.) in anhydrous benzene was added a solution of compound (3) (1.0 equiv.) in anhydrous benzene, dropwise at room temperature. The reaction mixture was then refluxed under nitrogen atmosphere overnight, cooled to room temperature, then stirred vigorously with 1N NaOH for 3 hours. The separated aqueous layer was acidified with 6N HCl, and the precipitated solid was then extracted with ethyl acetate. The combined organic extracts were washed with water to pH 5-6 for aqueous phase, dried over Na2 SO4 and concentrated to give 4-hydroxycoumarin (4) as an off-white solid (50-87percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With Eaton’s reagent In water for 2 h; Reflux | A mixture of malonic acid monophenyl ester (10) (1 mmol) and Eaton’s reagent (4 ml) was refluxed at 70°C for 2 h. Ice-cold waterwas then added to this mixture with continuous stirring. The precipitateswere filtered with suction, washed with water, dried and recrystallized from ethanol to afford 4-hydroxy coumarin (11).Yield and mp: 63percent, 217–18 C.42 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | at 60 - 65℃; | A mixture of phenol (19.8 g, 0.21 mol), anhydrous ZnCl2 (84.8 g, 0.62 mol), POC13 (97 g, 0.63 mol), and malonic acid (22 g, 0.21 mol) was heated at 60-65 °C for 40 h, then the mixture was cooled. After the mixture was decomposed with water, the solid was filtered. The solid was dissolved with 10percent aqueous Na2CO3, then acidified with diluted hydrochloric acid. The crystal was filtered to give the product 2a. 4-Hydroxycoumarin (2a) Yellow solid; yield 41percent, mp 211-213 °C. 1H NMR (300 MHz, DMSO) δ 12.57 (s, 1H, OH), 7.84 (d, J = 7.7 Hz, 1H, coumarin-5-H), 7.67 (dd, J = 11.4, 4.1 Hz, 1H, coumarin-7-H), 7.39-7.29 (m, 2H, coumarin-6, 8-H), 5.62 (s, 1H, coumarin-3-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; iron(III)-acetylacetonate In tetrahydrofuran at 0℃; for 0.166667 h; Inert atmosphere | Test tube in a nitrogen atmosphere under a tetrahydrofuran (2 mL) and the solvent in the acetylacetonate screen third iron {Fe (acac) 3 5.30 mg, 0.015 mmol} existing under 4-sulfamate coumarin (134.64 mg, 0.5 mmol) and DMPU (576 mg, 9eq) and 1,3-dimethyl -3,4,5,6-tetrahydro -2 (1H) - pyrimidyl dinon (576.76 mg, 4.5 mmol) and then mixed at 0 normal- It was added butyl magnesium chloride (116.87 mg, 1.0 mmol) slowly to give. If after 10 minutes the starting material is exhausted, then terminate the reaction with 1N HCl and extracted with diethyl ether, and after removing the solvent was separated by column chromatography to give the title compound, 4-butyl-coumarin (70percent). |
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