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CAS No. : | 63160-12-3 | MDL No. : | MFCD22199989 |
Formula : | C14H13NO3S | Boiling Point : | - |
Linear Structure Formula : | CH3C6H4SO2(C6H5)CHNO | InChI Key : | SYTQRZCKINWJKR-UHFFFAOYSA-N |
M.W : | 275.32 | Pubchem ID : | 10967742 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 74.77 |
TPSA : | 58.06 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.93 cm/s |
Log Po/w (iLOGP) : | 2.66 |
Log Po/w (XLOGP3) : | 2.88 |
Log Po/w (WLOGP) : | 3.01 |
Log Po/w (MLOGP) : | 2.7 |
Log Po/w (SILICOS-IT) : | 1.87 |
Consensus Log Po/w : | 2.62 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.63 |
Solubility : | 0.0644 mg/ml ; 0.000234 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.76 |
Solubility : | 0.048 mg/ml ; 0.000174 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.34 |
Solubility : | 0.0125 mg/ml ; 0.0000453 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.36 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P501 | UN#: | 1759 |
Hazard Statements: | H302-H318 | Packing Group: | Ⅲ |
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 |
---|---|---|
96% | With C26H36N4OS; 3-chloro-benzenecarboperoxoic acid In ethanol at -40℃; for 24 h; | General procedure: The corresponding imine (0.20 mmol), catalyst 2f (0.024 mmol) were dissolved in xylene (4.0 mL) at room temperature, and the mixture was stirred at room temperature for 5 min. Then, m-CPBA (purity 85percent, 0.24 mmol) was added at −40°C, stirring continued for the time indicated in Table 4, and the crude mixture was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=7:1) to provide the corresponding oxaziridines 3a–o. |
95% | With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform; water at 0℃; for 2 h; | To a mixed solution of saturated aqueous sodium bicarbonate (12 ml) and chloroform (10 ml), benzyltriethylammonium chloride (290 mg, 1.27 mmol) and N-benzylidene-4-toluenesulfonamide (Reference Example 144) (3.00 g, 11.6 mmol) were added, and a solution of m-chloroperbenzoic acid (2.58 g, 12.7 mmol) in chloroform (24 ml) was added dropwise thereto at 0°C with stirring. Thereafter, the resultant was stirred at the same temperature for 2 hours, and the mixture was gradually heated to room temperature. The reaction solution was extracted with chloroform, the organic layer was washed with saturated aqueous sodium bicarbonate, an aqueous solution of 5percent sodium bisulfite, and brine, dried (over potassium carbonate), and then concentrated under a reduced pressure. Hexane was added to the residue, the resulting slurry was filtered and washed, and a title compound (3.03 g,11.0 mmol, 95percent) was obtained as a white powder. 1H-NMR (400 MHz, CDCl3) δ: 2.50 (3H, s), 5.45 (1H, s), 7.40-7.47 (7H, m), 7.93 (2H, d, J = 8.4 Hz). ESI-MS: m/z = 276 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With C26H36N4OS; 3-chloro-benzenecarboperoxoic acid; In ethanol; at -40℃; for 24h; | General procedure: The corresponding imine (0.20 mmol), catalyst 2f (0.024 mmol) were dissolved in xylene (4.0 mL) at room temperature, and the mixture was stirred at room temperature for 5 min. Then, m-CPBA (purity 85%, 0.24 mmol) was added at -40C, stirring continued for the time indicated in Table 4, and the crude mixture was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=7:1) to provide the corresponding oxaziridines 3a-o. |
95% | With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In chloroform; water; at 0℃; for 2h; | To a mixed solution of saturated aqueous sodium bicarbonate (12 ml) and chloroform (10 ml), benzyltriethylammonium chloride (290 mg, 1.27 mmol) and N-benzylidene-4-toluenesulfonamide (Reference Example 144) (3.00 g, 11.6 mmol) were added, and a solution of m-chloroperbenzoic acid (2.58 g, 12.7 mmol) in chloroform (24 ml) was added dropwise thereto at 0C with stirring. Thereafter, the resultant was stirred at the same temperature for 2 hours, and the mixture was gradually heated to room temperature. The reaction solution was extracted with chloroform, the organic layer was washed with saturated aqueous sodium bicarbonate, an aqueous solution of 5% sodium bisulfite, and brine, dried (over potassium carbonate), and then concentrated under a reduced pressure. Hexane was added to the residue, the resulting slurry was filtered and washed, and a title compound (3.03 g,11.0 mmol, 95%) was obtained as a white powder. 1H-NMR (400 MHz, CDCl3) delta: 2.50 (3H, s), 5.45 (1H, s), 7.40-7.47 (7H, m), 7.93 (2H, d, J = 8.4 Hz). ESI-MS: m/z = 276 (M+H+). |
With sodium hypochlorite pentahydrate; In water; acetonitrile; at 20℃; for 0.5h; | 1.9743 g (12 mmol, 12 equivalents based on the substrate) of powder crystal of sodium hypochlorite pentahydrate (Nickel diazo pentahydrate, effective chlorine concentration 42%) was placed in a 50 mL recovery flask, and H 2 O 5. And dissolved in 5 mL to prepare a sodium hypochlorite aqueous solution.While confirming the pH of the aqueous solution with a pH meter, 12.5 M sodium hydroxide aqueous solution was added dropwise to adjust the pH to 14 and then cooled to 0 C. The imines (A1, 0.2590 g, 1 mmol) obtained in Synthesis Example 1 were placed in a separately prepared 30 mL flask and dissolved by adding 5 mL of water-containing acetonitrile.This acetonitrile solution was added to an aqueous sodium hypochlorite solution and stirred at 0 C. for 10 minutes.After lapse of 10 minutes, the reaction solution was brought to room temperature and further stirred for 20 minutes.After confirming that the raw material A1 (Rf = 0.45) had disappeared by thin layer chromatography (TLC, developing solvent Hexane: AcOEt = 3: 1, iodine coloration), H 2 O (50 mL) was added to the system , And extracted with AcOEt (30 mL × 3 times).The separated organic phase was washed with saturated aqueous sodium chloride solution.Anhydrous magnesium sulfate was put in the organic phase, dehydrated and dried, then it was removed by filtration operation, and the filtrate was distilled off with a rotary evaporator to give the oxaziridine compound (B1) (3-Phenyl-2-tosyl-1, 2-oxaziridine) as a white solid.As a by-product, benzaldehyde (C) was also obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate; | Step 5: Preparation of 4-hydroxy-2-(3-trifluoromethyl)phenyl-3-isoxazolidinone. Lithium bis(trimethylsilyl)amide (0.29 ml, 1M solution in tetrahydrofuran) was added slowly to a stirred solution of pure 2-(3-trifluoromethyl)phenyl-3-isoxazolidinone (0.06 g) in dry tetrahydrofuran (5 ml), maintaining the temperature below -75 C. The mixture was stirred for ten minutes at -78 C, allowed to warm to -25 C., recooled to -78 C., then treated with N(4-toluenesulphonyl)-3-phenyloxaziridine (0.08 g, prepared as described in J. Org. Chem., 1988, 53, 2087). It was stirred at -78 C. for a further one hour, allowed to warm to room temperature, poured on to saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using hexane-ethyl acetate (3:1) then ethyl acetate as eluants, to give a pale yellow solid (0.05 g) comprising a mixture of the title compound and toluene p-sulphonamide. This material can be used directly for carbamoylation and the t-butylcarbamate readily separated from toluene p-sulphonamide. 1 H NMR (CDCl3): title compound signals only: delta 4.0(1H,broad s), 4.35(1H,t), 4.8(1H,t), 4.95(1H,t), 7.5(2H,m), 7.95(2H,m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76%; 12% | Potassium hexamethyldisilazide (KHMDS; 0.20 mL of a 1.6 M solution in toluene, 0.30 mmol) in tetrahydrofuran (5 mL) was stirred and cooled to -78 C before a solution of the foregoing hexenoate 50 (85 mg, 0.20 mmol) in tetrahydrofuran (1 mL) was added dropwise. The resulting orange solution was stirred for 20 min then a solution of <strong>[63160-12-3]2-(4-toluenesulfonyl)-3-phenyloxaziridine</strong> 51 (78 mg, 0.30 mmol)refPreviewPlaceHolder28 was added. After a further 20 min at this temperature, saturated aqueous ammonium chloride (10 mL) was added, the resulting mixture warmed to ambient temperature, the layers separated and the aqueous layer extracted with ether (2×10 mL). The combined organic solutions were dried, filtered and evaporated. Column chromatography of the residue separated the hydroxy-ester52 (68 mg, 76%) as a pale yellow oily solid and a 3:1 mixture of diastereoisomers which showed: 1H NMR (400 MHz, CDCl3): delta=(major isomer) 7.78 (d, J=8.0 Hz, 1H, 7'-H), 7.55 (d, J=8.2 Hz, 2H, 2× ArH), 7.40-7.36 (m, 2H, 2'- and 4'-H), 7.19 (d, J=8.2 Hz, 2H, 2× ArH), 7.15-7.10 (m, 2H, 5'- and 6'-H), 5.43 (d, J=9.5 Hz, 1H, 4-H), 4.29 (d, J=3.8 Hz, 1H, 2-H), 4.08 (dd, J=9.5, 3.8 Hz, 1H, 3-H), 3.83-3.78 (m, 2H, OCH2), 2.14 (s, 3H, ArMe), 1.59 (s, 3H, Me), 1.53 (s, 3H, Me), 1.11 (t, J=7.1 Hz, 3H, CH2CH3); (minor isomer) 7.79 (d, J=8.1 Hz, 1H, 7'-H), 7.60 (d, J=8.2 Hz, 2H, 2× ArH), 7.40-7.36 (m, 2H, 2'- and 4'-H), 7.19 (d, J=8.2 Hz, 2H, 2× ArH), 7.15-7.10 (m, 2H, 5'- and 6'-H), 5.33 (d, J=9.3 Hz, 1H, 4-H), 4.36 (d, J=3.0 Hz, 1H, 2-H), 3.99 (dd, J=9.3, 3.0 Hz, 1H, 3-H), 3.83-3.78 (m, 2H, OCH2), 2.14 (s, 3H, ArMe), 1.58 (s, 3H, Me), 1.51 (s, 3H, Me), 0.85 (t, J=7.1 Hz, 3H, CH2CH3); 13C NMR (100 MHz, CDCl3): delta=(major isomer) 178.3 (CO), 150.4 (s), 143.8 (s), 134.8 (s), 129.9 (s), 129.8 (d), 128.8 (d), 127.0 (s), 126.7 (d), 124.7 (d), 122.3 (d), 119.6 (d), 113.7 (d), 73.7 (2-CH), 61.7 (OCH2), 39.5 (3-CH), 25.9 (q), 21.6 (q), 18.2 (q), 13.9 (q); (minor isomer) 177.2 (CO), 149.1 (s), 143.7 (s), 134.1 (s), 129.7 (s), 129.2 (d), 128.5 (d), 127.1 (s), 126.9 (d), 124.7 (d), 122.3 (d), 119.8 (d), 115.1 (d), 73.1 (2-CH), 61.9 (OCH2), 39.4 (3-CH), 26.0 (q), 21.6 (q), 18.3 (q), 14.1 (q) (two resonances obscured); IR (CHCl3): numax=3316, 2919, 1730, 1447, 1369 cm-1; m/z [APCI] 442 (M++H, 100%); HRMS: m/z: calcd for C24H28NO5S: 442.1683; found: 442.1685 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate; In 1,4-dioxane; at 20 - 25℃; for 18h;Molecular sieve; Inert atmosphere; | General procedure: To a flame-dried round bottom flask containing a stirrer bar and3 A molecular sieves were added a-aroyloxyaldehyde (0.2 mmol),oxaziridine (0.6 mmol), N-heterocyclic carbene precatalyst (10 mol%), cesium carbonate (0.22 mmol) and anhydrous 1,4-dioxane(4 mL) under an argon atmosphere. The reaction mixture wasallowed to stir at rt for 18 h. Sodium bisulfite solution (4 mL, aq.10% w/v) was added and the reaction stirred at rt for 4 h. The reactionmixture was diluted with Et2O (10 mL) and washed sequentiallywith water (10 mL), saturated aqueous NH4Cl (10 mL),saturated aqueous NaHCO3 (10 mL) and brine (10 mL). The organiclayer was dried over MgSO4, filtered and concentrated underreduced pressure. The crude residue was purified by flash columnchromatography to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride; caesium carbonate; In tetrahydrofuran; at 20 - 25℃; for 18h;Molecular sieve; Inert atmosphere; | General procedure: To a flame-dried round bottom flask containing a stirrer bar and3 A molecular sieves were added a-aroyloxyaldehyde (0.2 mmol),oxaziridine (0.6 mmol), N-heterocyclic carbene precatalyst (10 mol%), cesium carbonate (0.22 mmol) and anhydrous 1,4-dioxane(4 mL) under an argon atmosphere. The reaction mixture wasallowed to stir at rt for 18 h. Sodium bisulfite solution (4 mL, aq.10% w/v) was added and the reaction stirred at rt for 4 h. The reactionmixture was diluted with Et2O (10 mL) and washed sequentiallywith water (10 mL), saturated aqueous NH4Cl (10 mL),saturated aqueous NaHCO3 (10 mL) and brine (10 mL). The organiclayer was dried over MgSO4, filtered and concentrated underreduced pressure. The crude residue was purified by flash columnchromatography to give the title compound. |
Tags: 63160-12-3 synthesis path| 63160-12-3 SDS| 63160-12-3 COA| 63160-12-3 purity| 63160-12-3 application| 63160-12-3 NMR| 63160-12-3 COA| 63160-12-3 structure
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H311 | Toxic in contact with skin |
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H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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