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CAS No. : | 4825-75-6 | MDL No. : | MFCD03701200 |
Formula : | C8H7NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GAUKCDPSYQUYQL-UHFFFAOYSA-N |
M.W : | 133.15 | Pubchem ID : | 4068104 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 38.97 |
TPSA : | 26.03 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) : | -5.61 cm/s |
Log Po/w (iLOGP) : | 1.94 |
Log Po/w (XLOGP3) : | 2.11 |
Log Po/w (WLOGP) : | 2.14 |
Log Po/w (MLOGP) : | 1.45 |
Log Po/w (SILICOS-IT) : | 2.4 |
Consensus Log Po/w : | 2.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.66 |
Solubility : | 0.291 mg/ml ; 0.00218 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.29 |
Solubility : | 0.687 mg/ml ; 0.00516 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.27 |
Solubility : | 0.072 mg/ml ; 0.000541 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.27 |
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 |
---|---|---|
83% | With pyridine; for 3.5h;Reflux; | 1-(2-hydroxyphenyl)ethanone O-acetyl oxime (2) (2.89 g, 15 mmol) was heated under reflux with anhydrous pyridine (25 mL) for 3.5 h. Following reflux, the dark yellow reaction mixture was allowed to cool to room temperature and acidified with 5 N HCl (approximately 100 mL). The mixture was extracted with ether (3 × 75 mL). The ether layers were pooled, washed with 1 N HCl (75 mL), dried over anhydrous sodium sulfate, and evaporated under vacuum to give yellow-colored, oily residue as crude product. The crude product was purified using column chromatography with hexane/EtOAc (25:2) as the eluting solvent. Fractions containing the desired compound were combined and dried under vacuum to give 3 as colorless oil. Rf = 0.70 (hexane - EtOAc, 5:1); Yield: 82%; 1H NMR (CDCl3, ppm) δ: 7.70 (d, 1H, J = 7.10 Hz, Ar-H), 7.60-7.55 (m, 2H, Ar-H), 7.31 (m, 1H, Ar-H), 2.30 (s, 3H, CH3); 13C NMR (CDCl3, ppm) δ: 162.8 (C), 154.5 (C), 130.5 (CH), 123.5 (CH), 122.2 (C), 121.6 (CH), 108.5 (CH), 12.8 (CH3); ESI-MS: 134.10(C8H7NO [M + H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 10h;Reflux; | To a solution of 3-methylbenzo[d]isoxazole (10.3 g, 77 mmol) in CC14 (200 mL) was added N-bromosuccinimide (NBS) (16.5 g, 93 mmol) and benzoyl peroxide (BPO) (5.6 g, 22 mmol). The resulting solution was heated to reflux for 10 hours The solids were filtered off and the filtrate was concentrated in vacuo to afford crude 3-(bromomethyl)benzo[d]isoxazole as a green oil (15.3 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With trifluoromethylsulfonic anhydride; In dichloromethane; at 20℃; for 5h;Inert atmosphere; | General procedure: The desired 2-hydroxyaryl aldoxime or ketoxime (2.0 mmol) in 5 mL dry DCM was taken in an oven-dried round-bottom flask. To the reaction mixture was adde ddropwise triflic anhydride (2.0 mmol) in DCM under nitrogen for 15 min. The reaction mixture was stirred at rt and the progress of the reaction was monitored by TLC and GC-MS (Table 1). After completion of reaction, the contents were poured on tocrushed ice (100 mL), neutralized with 10% NaHCO3 solution (20 mL), and extracted with DCM (315 mL). The pure products were obtained by column chromatography with hexane-ethyl acetate mixture (80:20). All the 1,2-benzisoxazole derivatives were characterized by GC-MS, 1H and 13C NMR, and elemental analysis, and the results are compared with authentic samples. |
93% | With sodium chlorodifluoroacetate; potassium carbonate; In N,N-dimethyl acetamide; at 85℃; for 0.583333h;Microwave irradiation; | 0.304 g (2 mmol) of 2-hydroxyacetophenone oxime was weighed separately,0.457 g (3 mmol) of sodium difluorochloroacetate,0.417 g (3 mmol) of potassium carbonate in 50 mL of a three-necked flask,Add 2 mL of N, N-dimethylacetamide as solvent,Magnetic stirring evenly into the microwave catalytic synthesis instrument,Manually set the parameters (microwave power 300W,Temperature 85 , microwave time 35min),Microwave reaction. After completion of the reaction, the mixture was cooled to room temperature, and 10 mL of deionized water and 10 mL of ethyl acetate were added to the reaction system for extraction,The organic phase was separated and washed three times with 10 mL of deionized water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated in vacuo to give the crude product.The crude product was purified by silica gel column chromatography (ethyl acetate / petroleum ether = 1: 20) to give 0.249 g of 3-methylbenzisoxazole in 93% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
d) 4-[2-[1,2-Benzisoxazol-3-yl]ethyl]-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) ester. A mixture of 3-methyl-1,2-benzisoxazole (0.410 g, 3.08 mmol) and the iodide formed in step c (1.05 g, 3.23 mmol) in dry THF (3.2 mL) was cooled to -78 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With selenium(IV) oxide; In 1,4-dioxane; water; for 48h;Reflux; | A mixture of selenium dioxide (1.10 g, 10 mmol), 5 mL water, and 20 mL of dioxane was heated with stirring until dissolution, and <strong>[4825-75-6]3-methylbenzo[d]isoxazole</strong> (3)(2.66 mL, 20 mmol) in 10 mL of dioxane were added and refluxed for 48 h with stirring. The selenium (about 80%, 0.88 g) was filtered off after cooling at room temperature, 2 mL of conc. HCl was added and solvent removed in vacuo on water bath below 50 C. To the dark oily residue was added excess of potassium carbonate and ether, the ethereal layer was dried over sodium sulfate, after removal of solvent the residue was fractioned to give colorless oil. Rf = 0.65 (hexane - EtOAc, 9:1); Yield: 85%; 1H NMR (CDCl3, ppm) δ: 9.50 (s, 1H, CHO), 7.75 (d, 1H, J = 7.10 Hz, Ar-H), 7.66-7.55 (m, 2H, Ar-H), 7.25 (m, 1H, Ar-H); 13C NMR (CDCl3, ppm) δ: 190.2 (C), 161.5 (C), 147.5 (C), 130.6 (CH), 124.1 (CH), 121.9 (C), 120.6 (CH), 108.8 (CH); ESI-MS:148.04 (C8H5NO2 [M + H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With n-butyllithium; diisopropylamine; In tetrahydrofuran; water; ethyl acetate; | Example 22 3-But-3-enyl-benzo[d]isoxazole (26) 3.0 mL dry THF was added to an oven-dried 25 mL flask and cooled to -78 C. on a dry ice/isopropanol bath. Diisopropylamine (840 μl, 6.0 mmol) was added followed by n-BuLi (3.8 mL, 1.6 M, 6.0 mmol). The LDA-solution that was obtained was left at room temperature. Compound 25 (666 mg, 5.0 mmol) was dissolved in 10 mL dry THF and added to an oven-dried 50 mL flask followed by allylbromide (476 μl, 5.5 mmol). The freshly prepared LDA-solution was slowly added at -78 C. and the mixture was left at room temperature for 30 min. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated to dryness to produce 893 mg of a light brown oil. Crude product was purified by column chromatography (heptane:ethyl acetate; 9:1; isocratic) to produce pure 26 (355 mg, 41%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride; potassium carbonate; In water; ethyl acetate; N,N-dimethyl-formamide; | Example 21 3-Methyl-benzo[d]isoxazole (25) Acetic anhydride (7.1 mL, 75 mmol) was added to 24 (7.55 g, 50 mmol) in a 100 mL flask. The mixture was heated to 60 C. for 3 hours followed by evaporation to dryness. Potassium carbonate (8.7 g, 63 mmol) was partly dissolved in 40 mL DMF and added to the mixture. The mixture was stirred at room temperature overnight and finally heated to 100 C. for 30 minutes. Ethyl acetate and water were added. The phases were separated and the aqueous phase was extracted with ethyl acetate and dichloromethane. The combined organic phases were dried over magnesium sulphate and evaporated to dryness to give 5.6 g of a yellow oil. Crude product was purified by column chromatography (100% dichloromethane), producing pure 25 (4.6 g). 1H NMR (CDCl3) δ 2.6 (s, 3H), 7.3 (m, 11H), 7.55 (m, 2H), 7.65 (m, 11H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With N-chloro-succinimide; potassium carbonate; In tetrahydrofuran; at 20℃; for 10h; | A mixture of 2-(l-iminoethyl)phenol (14.7 g, 108.7 mmol) and potassium carbonate (30 g, 217 mmol) in tetrahydrofuran (150 mL) was treated with N- chlorosuccinimide (NCS) (22 g, 164.7 mmol) for 10 hours at room temperature. The resulting mixture was quenched with water (300 mL) and extracted with ethyl acetate (4 x 100 mL). The combined organic layers were washed with brine (2 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford a residue, which was purified by a silica gel column chromatography eluting with 1 % ethyl acetate in petroleum ether to afford 3-methylbenzo[d]isoxazole as a light green liquid (8.8 g, 61 ). LC/MS (ES, m/z): [M+H]+ 134.0 *H NMR (300 MHz, DMSO) δ 7.65 - 7.62 (d, J = 7.80 Hz, 1H), 7.57 - 7.51 (m, 2H), 7.34 -7.26 (m, 1H), 2.60 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium phosphate; fac-Ir(ppy)3; In dimethyl sulfoxide; at 20℃; for 48h;Inert atmosphere; Schlenk technique; Sealed tube; UV-irradiation;Catalytic behavior; | General procedure: The oven-dried Schlenk tube (10 mL) containing a stirring bar was charged with benzo[d]isoxazoles 1 (0.5 mmol, 1.0 equiv.), BrCF2CO2Et (202.98 mg, 1.0 mmol, 2.0 equiv.), K3PO4 (212.27 mg, 1.0 mmol, 2.0 equiv.) and fac-Ir(ppy)3 (6.55 mg, 0.01 mmol, 0.02 equiv.). Then the tube was sealed and evacuated and back-filled with nitrogen for 3 times. Last, anhydrous DMSO (1 mL) was added via syringe. The resulting mixture was irradiated by 8 W blue LEDs light (460-470nm) in room temperature for 48 h. Then, the mixture extracted by ethyl acetate (10 mL), washed with water (10 mL×3) and dried over Na2SO4, the solvents were evaporated under vacuo, and the obtained crude product was purified by silica gel column chromatography (petroleum ether/AcOEt = 20/1) to give the pure desired product 2. |
Tags: 4825-75-6 synthesis path| 4825-75-6 SDS| 4825-75-6 COA| 4825-75-6 purity| 4825-75-6 application| 4825-75-6 NMR| 4825-75-6 COA| 4825-75-6 structure
[ 118251-97-1 ]
3,4,6-Trimethylbenzo[d]isoxazole
Similarity: 0.94
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