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CAS No. : | 89-73-6 | MDL No. : | MFCD00002110 |
Formula : | C7H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HBROZNQEVUILML-UHFFFAOYSA-N |
M.W : | 153.14 | Pubchem ID : | 66644 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 37.38 |
TPSA : | 69.56 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.62 cm/s |
Log Po/w (iLOGP) : | 0.65 |
Log Po/w (XLOGP3) : | 0.86 |
Log Po/w (WLOGP) : | 0.51 |
Log Po/w (MLOGP) : | 0.54 |
Log Po/w (SILICOS-IT) : | -0.04 |
Consensus Log Po/w : | 0.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.6 |
Solubility : | 3.82 mg/ml ; 0.025 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.9 |
Solubility : | 1.91 mg/ml ; 0.0125 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.23 |
Solubility : | 9.0 mg/ml ; 0.0587 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.1 |
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 |
---|---|---|
89% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h; | General procedure: To a solution of N-hydroxysalicylamide (0.5 g, 3.26 mmol) in anhydrous DMF (5 ml) was added 2a or 2b (3.26 mmol) and freshly calcinated K2CO3 (1.35 g, 9.78 mmol) and the mixture was kept, with stirring at the room temperature overnight. DMF was removed in vacuo and the residue was treated with water (10 ml) and then extracted with CH2Cl2 (5 ml). The organic layer was separated, washed with water, dried over anhydrous CaCl2, and purified by flesh chromatography on silica gel using CH2Cl2 as eluent. Dichloromethane was evaporated in vacuo. The resulting residue was benzo[d]oxazol-2(3H)-one 11. The water layer was acidify by hydrochloric acid, filtered and washed with water. The resulting residue was compound 12a(b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 60℃; for 2.5 h; Heating / reflux Stage #2: With hydrogenchloride In water at 10 - 15℃; for 0.5 h; |
A solution of intermediate 1 (1,92 M in THF) was stirred at 60°C. A solution of CDI (3,84 M in THF) was added over 30 min. under reflux to the aforementioned solution and refluxed for another 2 hours at 60°C. The reaction mixture was cooled to 40°C and the solvent evaporated. After completion, the remaining residue was quenched with water and acidified with 12N HCI to pH 2. The mixture was stirred for 30 min. at 10- 15°C and the resulting precipitate filtrated, washed with ice-water and dried under reduced pressure at 90 °C. Quantitative Yielding 3-Hydroxybenzisoxazole (intermediate 2). |
95% | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.533333 h; Inert atmosphere | Salicylhydroxamic acid 1a (77 mg, 0.5 mmol, 1 equiv) was dissolved in anhydrous THF (7 mL) under an inert (N2) atmosphere. Triphenylphosphine (164 mg, 0.625 mmol, 1.25 equiv) was then added. After 2 min, DIAD (123 lL, 0.625 mmol, 1.25 equiv) was added dropwise. TLC (Hex/EtOAc, 1:3) after 30 min revealed the reaction was complete. The THF was removed in vacuo. The residue was partitioned between 0.1 M NaOH (50 mL)and CH2Cl2 (100 mL). The organic layer was separated, then the aqueous layerwas washed a further three times with CH2Cl2 (100 mL). The aqueous layer was acidified with 1 M HCl (10 mL), then extracted into CH2Cl2 (2 100 mL),washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to yield the 3-hydroxybenzisoxazole 2a: mp = 143 146 C; δH (400 MHz, d6-DMSO)7.09–7.17 (m, 3H, Ar), 7.29 (d, J = 7.6 Hz, 1H, Ar), 11.63 (s, 1H, OH); δC(100 MHz, CDCl3) 156.2, 143.8, 129.4, 124.2, 122.7, 110.2, 110.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With 1,1'-carbonyldiimidazole In tetrahydrofuran; methanol; water | Example 67 Benzo[d]isoxazol-3-ol (35AKU-44) (71) To a solution of salicylhydroxamic acid (1.53 g, 10 mmol) in THF (40 ml) was added a solution of carbonyldiimidazole (1.62 g, 20 mmol) in tetrahydrofuran (20 ml). The mixture was stirred at reflux for 4 hrs. before evaporation to dryness. Water (20 ml) and conc. HCl (aq.) (5 ml) were added and the solution was refrigerated (5° C.) for 30 min. The resulting precipitate was collected by filtration and washed with 2M HCl. The solid material was dissolved in methanol and concentrated in vacuo yielding 725 mg (54percent) of the title compound 71. TLC (10percent methanol in DCM): Rf=0.2. HPLC-MS (Method A): M+=136.1 (UV/MS(percent)=94/100).1H-NMR (400 MHz, CDCl3, MeOD): δ=7.73 (1H, m); 7.56 (1H, m); 7.38 (1H, m); 7.28 (1H, m); 3.87 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With menadione; hydroxylamine hydrochloride; water; silver nitrate; triethylamine In tetrahydrofuran; ethanol at 20℃; for 0.5 h; Irradiation; Green chemistry | General procedure: To an aqueous solution of AgNO3 (1.7 mg, 0.01 mmol, 1 molpercent) in water (6 mL),vitamin K3 (2.6 mg, 0.015 mmol, 1.5 molpercent) dissolved in ethanol (2 mL) wasadded, and then an appropriate aldehyde (1 mmol) dissolved in THF (2 mL) wasadded to the reaction mixture followed by the addition of NH2OHHCl (69 mg,1 mmol) and Et3N (0.14 mL, 1 mmol). The final solvent ratio (H2O:EtOH:THF)was (3:1:1). The mixture was stirred at room temperature for 30 min under visiblelight irradiation using a halogen lamp (HALOPAR 20 75 W 230 V 30-GU10;Osram, Italy). The reaction was monitored by TLC. After completion of thereaction, EtOAc (30 mL) was added. The aqueous layer was collected andconcentrated under reduced pressure at 25 C to obtain pure sample containing Agnanoparticles that was characterized by UV–Vis and TEM analyses. The organicphase was collected, dried over anhydrous MgSO4 and filtered. The solvent wasevaporated under vacuum using a rotatory evaporator and then the residue was purified by a short plug of silica gel using (Hexane:EtOAc, 1:1) to obtainhydroxamic acids 2a–j in 81–92percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydroxide; hydroxylamine In 1,4-dioxane; water at 20℃; for 12 h; | A solution of hydroxylamine (3M) was stirred at RT under N2-atmosphere, then NaOH (7.05 mol in 240 ml H2O) and methyl salicylate (300 g in 750 ml dioxane) were added dropwise and the reaction mixture was stirred for 12 hours at RT. After completion, the reaction solvent was evaporated at 50°C, the remaining residue cooled and acidified with 12N HCI. The mixture was stirred for 30 min. at 10-15°C and the resulting precipitate filtrated, washed with ice-water and dried under reduced pressure at 90 °C. Ouantitative Yielding 2-Hvdroxybenzhvdroxamic Acid (intermediate 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h; | General procedure: To a solution of N-hydroxysalicylamide (0.5 g, 3.26 mmol) in anhydrous DMF (5 ml) was added 2a or 2b (3.26 mmol) and freshly calcinated K2CO3 (1.35 g, 9.78 mmol) and the mixture was kept, with stirring at the room temperature overnight. DMF was removed in vacuo and the residue was treated with water (10 ml) and then extracted with CH2Cl2 (5 ml). The organic layer was separated, washed with water, dried over anhydrous CaCl2, and purified by flesh chromatography on silica gel using CH2Cl2 as eluent. Dichloromethane was evaporated in vacuo. The resulting residue was benzo[d]oxazol-2(3H)-one 11. The water layer was acidify by hydrochloric acid, filtered and washed with water. The resulting residue was compound 12a(b). |
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