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CAS No. : | 1207453-90-4 | MDL No. : | MFCD22370184 |
Formula : | C8H4FNO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JBLFHMWQMPVDDL-UHFFFAOYSA-N |
M.W : | 197.12 | Pubchem ID : | 57519176 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.55 |
TPSA : | 72.12 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) : | -6.59 cm/s |
Log Po/w (iLOGP) : | 1.06 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | 1.67 |
Log Po/w (MLOGP) : | 1.69 |
Log Po/w (SILICOS-IT) : | 0.38 |
Consensus Log Po/w : | 1.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.5 mg/ml ; 0.00759 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.39 |
Solubility : | 0.796 mg/ml ; 0.00404 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.24 |
Solubility : | 1.13 mg/ml ; 0.00573 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.28 |
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 |
---|---|---|
79% | With water In 1,4-dioxane for 96 h; Reflux | A mixture of methyl 5-fluoro-2-methyl-3-nitrobenzoate (28 g, 130.5 mmol), NBS (27.8 g, 156.6 mmol) and BPO (3.13 g, 13.1 mmol) in CCl4 (400 mL) was heated to reflux overnight. TLC (petroleum ether/EtOAc=15:1) showed the starting material was consumed completely. Water (200 mL) was added and CCl4 was removed under reduced pressure. The residue was extracted with DCM (200 mL.x.3). The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give crude methyl 2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate (36 g, yield 94percent) as a brown oil. A mixture of methyl 2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate (36 g, 123 mmol) in 1,4-dioxane (250 mL) and water (62.5 mL) was heated to reflux for 4 days. TLC (petroleum ether/EtOAc=15:1) showed the starting material was consumed completely. Dioxane was removed under reduced pressure. The residue was extracted with EtOAc (300 mL.x.4). The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give crude product. The crude product was purified by gel chromatography (petroleum ether to petroleum ether/EtOAc=5:1) to give 6-fluoro-4-nitroisobenzofuran-1(3H)-one (19.2 g, yield 79percent) as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 5.74 (s, 2H), 7.97-7.98 (dd, 1H), 8.24-8.27 (dd, 1H); LC-MS (ESI) m/z: 198(M+1)+ |
79% | for 96 h; Reflux | Example 63B6-Fluoro-4-nitroisobenzofuran- 1 (3H)-one[00598] A mixture of methyl 5-fluoro-2-methyl-3-nitrobenzoate (28 g, 130.5 mmol), NBS (27.8 g, 156.6 mmol) and BPO (3.13 g, 13.1 mmol) in CC14 (400 mL) was heated to reflux overnight. TLC (petroleum ether/ EtOAc = 15: 1) showed the starting material was consumed completely. Water (200 mL) was added and CC14 was removed under reduced pressure. The residue was extracted with DCM (200 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, concentrated to give crude methyl 2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate (36 g, yield 94percent) as a brown oil. A mixture of methyl 2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate (36 g, 123 mmol) in 1, 4-dioxane (250 mL) and water (62.5 mL) was heated to reflux for 4 days. TLC (petroleum ether / EtOAc = 15: 1) showed the starting material was consumed completely. Dioxane was removed under reduced pressure. The residue was extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine, dried over Na2S04, concentrated to give crude product. The crude product was purified by gel chromatography (petroleum ether to petroleum ether/ EtOAc = 5: 1) to give 6-fluoro-4- nitroisobenzofuran-l(3H)-one (19.2 g, yield 79percent) as a white solid. ^-NMR (400 MHz, CDC13) δ (ppm): 5.74 (s, 2H), 7.97-7.98 (dd, 1H), 8.24-8.27 (dd, 1H); LC-MS (ESI) m/z: 198(M+1)+. |
2.3 g | Reflux | Amixtureofthecrudecompound5methyl2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate(4.5g)in1,4-dioxane(15mL)andwater(3mL)washeatedtorefluxovernight.TLC(petroleumether/EtOAc=5:1)showedthestartingmaterialwasconsumedcompletely. Dioxanewasremovedunderreducedpressure.TheresiduewasextractedwithEtOAc(15mL×4).Thecombinedorganiclayerswerewashedwithbrine,driedoverNa 2SO 4,concentratedtogivethecrudeproduct.Thecrudeproductwaspurifiedbygelchromatography(petroleumethertopetroleumether/EtOAc=5/1)togivecompound6,6-fluoro-4-nitroisobenzofuran(2.3g,83.3percentyield,twosteps)asawhitesolid. 1HNMR(400MHz,CDCl 3):δ(ppm)8.25(dd,J=7.8,2.2Hz,1H),7.97(dd,J=6.0,2.0Hz,1H),5.12(d,J=2.0Hz,2H) |
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