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CAS No. : | 61348-47-8 | MDL No. : | MFCD00218653 |
Formula : | C9H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DBDXTIAEVFSDNN-UHFFFAOYSA-N |
M.W : | 161.16 | Pubchem ID : | 578506 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.96 |
TPSA : | 46.26 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) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 1.73 |
Log Po/w (XLOGP3) : | 1.68 |
Log Po/w (WLOGP) : | 2.05 |
Log Po/w (MLOGP) : | 0.85 |
Log Po/w (SILICOS-IT) : | 1.97 |
Consensus Log Po/w : | 1.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.51 |
Solubility : | 0.498 mg/ml ; 0.00309 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.27 |
Solubility : | 0.873 mg/ml ; 0.00542 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.17 |
Solubility : | 0.109 mg/ml ; 0.000678 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.36 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
5.22 g | With hydroxylamine hydrochloride; In ethanol; at 78℃; for 1h; | To a 100 mL flask was added 15 mL N-methylpyrrolidone, 1-(2-hydroxyphenyl) ethanone (5.03 g, 36.87mmol) and dimethoxy-N,N-dimethylmethanamine (6.21 g, 52.15 mmol) at room temperature. Thereaction mixture was heated to 90 C, stirred at 90 C for 40 min, then cooled to room temperature.Ethanol (50 mL) and hydroxylamine hydrochloride (3.84 g, 55.19 mmol) were added, then the solutionwas heated to 78 C and stirred for 1 h. The reaction mixture was concentrated. The residue washeated to 45 C, then, 125 mL water was added dropwise over 0.5 h. The solution was stirred at 45 Cfor 30 min, then cooled to room temperature and stirred overnight before the solid was collected byfiltration, washed with 20 mL water and dried in an evaporator at 50 C for 4 h to afford 2-(isoxazol-5-yl)phenol as a white solid 5.22 g, (87.7%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.3% | With potassium carbonate; In ethanol; water; at 75℃; for 19h; | To a 250 mL flask was added 2-(isoxazol-5-yl)-3-methoxyphenol (5.02 g, 31.15 mmol), potassiumcarbonate (6.03 g, 43.63 mmol), ethanol (50 mL), and water (25 mL) at room temperature. Thereaction mixture was heated to 90 oC (oil bath temperature) and stirred for 19 h. The solution wasconcentrated, then, dichloromethane (50 mL) was added. The solution was stirred at roomtemperature for 1 h, then, filtered. The solid product was washed with water (2.5 mL) anddichloromethane (25 mL) then dried in an evaporator at 50 C to afford 2-amino-5-methoxy-4Hchromen-4-one (4.38 g, 87.3% yield) as a light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; at 20℃; | Triethylamine (8. 0g, 0. [079MOL)] was added to a stirred solution of [E- (3-] styrenesulphonyl chloride [(12.] 0g, 0. [059MOL)] and 4-hydroxypiperidine (8. 0g, 0. [079MOL)] in THF (100ml) at RT. Stirring was continued overnight before the reaction mixture was reduced to low volume and partitioned between EtOAc followed by aqueous 1M [HC1,] saturated [NAHCO3] and brine. The organic fraction was then dried [(NA2SO4)] and evaporated to give a solid product. (12.75g ; 0. 046mol) ; NMR (CDC13) : 1.5-1. 8 (m, 4H), 1.9-2. 1 (m, 2H), 3.0-3. 2 (m, 2H), 3.4-3. 6 (m, 2H), 3.85 (s, 1H), 6.65 (s, 1H), 7.3-7. 6 (m, 6H); MS: 268. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 20℃; | 2- (5-Isoxazolyl)-phenol (121mg, 0. 75mmol) was dissolved in DCM [(LML)] and E-1- (4- [HYDROXYPIPERIDIN-L-YLSULPHONYL)-2-PHENYLETHENE] (0.2g, 0. [75MMOL)] was added. A solution of triphenylphosphine (0.2g, 0.75mmol) in DCM [(2ML)] followed by a solution of DIAD (0. [15ML,] 0. [75MMOL)] in DCM (2ml) was then added and the resulting mixture stirred at RT overnight. The mixture was concentrated and purified by chromatography: bond elute cartridge, eluent hexane (5 minutes; 20 mUminute), 100% hexane to 100% DCM (15 minutes) to give [E- [4- (2-] (5-isoxazolyl) phenyloxy) [PIPERIDIN-1-YLSULPHONYL]-2-PHENYLETHENE,] which was carried through to the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With hydrazine; In dimethyl sulfoxide; at 90℃; for 15h;Sealed tube; | General procedure: Into a reaction vessel was added 5-(4-chlorophenyl)isoxazole (1a) (997 mg, 5.55 mmol), DMSO (5 mL), and hydrazine (433 mg of 64wt %, 8.65 mmol, 1.6 equiv). The vessel was sealed and heated at 90 C for 15 h, then cooled to 20 C. H2O (15 g) was added, resulting in the precipitation of product. The slurry was cooled in ice-H2O for 1.5 h and filtered. The wet cake was washed with H2O (2 × 10 mL) and dried, resulting in 3-(4-chlorophenyl)-1H-pyrazol-5-amine (2a) (925mg of 93 wt %, 99.6 area %, 4.46 mmol, 80% yield). Another 4% yield was contained in the mother liquor. |
59% | General procedure: Into a reaction vessel was added KOH (391 mg of 85 wt %, 5.92 mmol, 1.04 equiv), EtOH (2.9 mL), and H2O (2.0 mL). The mixture was stirred until a solution resulted. Next, 5-(4-chlorophenyl)isoxazole (1a) (1026 mg, 5.71 mmol) was added, forming a slurry. The vessel was sealed and heated at 50 C for 0.5 h, consuming the starting material and resulting in a solution. After cooling to 20 C, THF (4.3 mL) and HOAc (706 mg, 11.76 mmol, 2.1 equiv) were added, resulting in a slurry. Finally, hydrazine (413 mg of 64 wt %, 8.25 mmol, 1.4 equiv) was added, resulting in a solution. The mixture was heated at 60 C for 2.5h, then cooled to 20 C. The reaction mixture was quenched with saturated aq Na2CO3 (3.1 mL, 5.1 mmol, 0.9 equiv), resulting in pH 11. The phases were separated. To the organic phase was added H2O (30 mL), resulting in the precipitation of product. The slurry was filtered. The wet cake was washed with H2O (2 × 10 mL) and dried at 40 C, resulting in 3-(4-chlorophenyl)-1H-pyrazol-5-amine (2a) (910 mg of87 wt %, 99.7 area %, 4.07 mmol, 71% yield). A second crop (140 mg of64.9 wt %, 0.48 mmol, 8% yield) was recovered from the mother liquor by extracting with MTBE (2 × 25 mL), drying over Na2SO4, and concentrating to dryness. |
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