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CAS No. : | 5735-53-5 | MDL No. : | MFCD02181098 |
Formula : | C8H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YRLORWPBJZEGBX-UHFFFAOYSA-N |
M.W : | 135.16 | Pubchem ID : | 585096 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.06 |
TPSA : | 21.26 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) : | -5.95 cm/s |
Log Po/w (iLOGP) : | 1.66 |
Log Po/w (XLOGP3) : | 1.65 |
Log Po/w (WLOGP) : | 0.92 |
Log Po/w (MLOGP) : | 1.09 |
Log Po/w (SILICOS-IT) : | 1.93 |
Consensus Log Po/w : | 1.45 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.16 |
Solubility : | 0.932 mg/ml ; 0.00689 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.71 |
Solubility : | 2.64 mg/ml ; 0.0195 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.71 |
Solubility : | 0.265 mg/ml ; 0.00196 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.82 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
65% | With potassium carbonate In N,N-dimethyl-formamide at 125℃; for 15 h; | To a suspension of 2-aminophenol (1.0 g, 9.2 mmol) and potassium carbonate (6.36 g, 46 mmol) in dry DMF (10 mL) was added 1, 2-dibromoethane (2.59 g, 13.8 mmol). The mixture was then heated at 125'C for 15 hours. After cooling, the mixture was treated with crushed ice and extracted with ethyl acetate. The organic extracts were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel using ethyl acetate/petroleum ether 1:10 (v:v) as eluent to give 3,4- dihydro-2H-benzo[b][1,4]oxazine as reddish oil (0.81 g, 65percent). LC-MS (ES-API); rt 7.51 min; m/z calculated for C8H9NO [M+Hf 136.1, found 136.1. |
29% | With potassium carbonate In water; acetone for 24 h; Reflux | 1 , 2-Dibromoethane (1.51 g, 13.87 mmol) was dissolved in 100 mL of acetone and a solution of 3.19 g of K2CO3 in 30 mL of water was added. A solution of 2-aminophenol in 10 mL of acetone suspension was added slowly to the suspension. The solution was heated to reflux for 24 hours. The acetone was evaporated to dryness. The residue was dissolved in water and extracted with dichloromethane . The combined organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by chromatography eluted with petroleum ether :ether acetate=50:l to 10:1 to obtain 450 mg of the target product as brown oil (yield: 29percent, ) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6 h; Inert atmosphere; Sealed tube | Under argon atmosphere, NaOH and triethyl boron were first stirred at room temperature to form a clear clear solution at a concentration of 1 M / L;Subsequently, 10 mol (2 molpercent) of the above-mentioned triethylboron solution, 5 mmol of amide substrate, 15 mmol of silane, 2 mL of solventInto a 10 mL sealed tube and placed in an oil bath at 80 ° C for 6 hours with heating. The reaction was completed and the reaction was exposed to air quenching, followed byThe yield was determined by column chromatography and gas chromatography and a pure product was obtained. When using polymethylhydrogensiloxane (PMHS) andWhen the tetrahydrofuran was used as the silane and the solvent, the yields of the products A and B were 81percent and 3percent, respectively. When the triethoxysilaneAnd n-hexane as silane and solvent, respectively, the yield of products A, B were: 90percent, 7percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: With sodium hydride In dichloromethane at 0℃; for 0.0833333 h; Inert atmosphere Stage #2: at 25 - 30℃; for 15 h; Inert atmosphere |
General procedure: A stifling solution of the requisite phenol derivative, (10 mmol) in CH2Cl2 (20 mL) was treated with NaH (35 mmol) at 0° C. under argon. After 5 minutes, 2-bromoethyldiphenylsulfonium salt (12 mmol) was added and the reaction was stirred for 5 hours at RT. The reaction was then quenched with saturated ammonium chloride solution (10 mL), and extraction was performed with CH2Cl2 (3×25 mL), washed with brine (20 mL), the resultant was dried over MgSO4, filtered and concentrated under vacuum. The targeted compound was then purified using chromatography on silica. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuranHeating / reflux Stage #2: With sodium hydroxide; water In tetrahydrofuran |
Synthesis of 3,4-dihydro-2H-benzo[b][1,4]oxazine Into a 250 mL 3-necked round-bottom flask, was placed a solution of lithium aluminum hydride (3.6 g, 94.74 mmol) in THF (80 mL). The mixture was stirred for 15 min. This was followed by the addition of a solution of 2H-benzo[b][1,4]oxazin-3(4H)-one (5.7 g, 38.22 mmol) in THF (21 mL), which was added dropwise with stirring. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by TLC (EtOAc/PE=1:1). The reaction mixture was then quenched by the adding 3.6 mL of H2O and 10.8 mL 15percent NaOH. A filtration was performed. The filter cake was washed 1 time with 30 mL of THF. The resulting solution was extracted two times with 100 mL of EtOAc and the organic layers combined and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 4.8 g (79percent) of 3,4-dihydro-2H-benzo[b][1,4]oxazine as a red oil. |
79% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 16 h; Heating / reflux Stage #2: With sodium hydroxide In tetrahydrofuran; water |
A solution of 2H-benzo[b][1,4]oxazin-3(4H)-one (38.2 mmol) in tetrahydrofuran (21 mL) was slowly added to a suspension of lithium aluminum hydride (94.7 mmol) in tetrahydrofuran (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was diluted with water (3.6 mL) and 15percentsodium hydroxide (10.8 mL) and the insoluble solids were removed by filtration. The aqueous layer was extracted with ethyl acetate (2 x 100 mL) and the combined organic layers were dried (sodium sulfate) and concentrated to provide 3,4-dihydro-2H-benzo[b][1,4]oxazine in 79percent yield as red oil. |
79% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuranHeating / reflux Stage #2: With sodium hydroxide In water |
Synthesis of 3,4-dihydro-2H-benzo[b][1,4]oxazine Into a 250 mL 3-necked round-bottom flask, was placed a solution of lithium aluminum hydride (3.6 g, 94.74 mmol) in THE (80 mL). The mixture was stirred for 15 minutes. This was followed by the addition of a solution of 2H-benzo[b][1,4]oxazin-3(4H)-one (5.7 g, 38.22 mmol) in THF (21 mL), which was added dropwise with stirring. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). The reaction mixture was then quenched by the adding 3.6 mL of H2O and 10.8 mL 15percentNaOH. A filtration was performed. The filter cake was washed 1 time with 30 mL of THF. The resulting solution was extracted two times with 100 mL of ethyl acetate and the organic layers combined and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 4.8 g (79percent) of 3,4-dihydro-2H-benzo[b][1,4]oxazine as red oil. |
79% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuranReflux Stage #2: With water; sodium hydroxide In tetrahydrofuran |
Intermediate 31: Synthesis of 4-methyl-3,4-dihydro-2H-benzo[b][l,4]oxazine-6-sulfonyl chloride.1. Synthesis of 3,4-dihydro-2H-benzo|"b"||"l,4"|oxazine.A solution of 2H-benzo[b][l,4]oxazin-3(4H)-one (38.2 mmol) in tetrahydrofuran (21 mL) was slowly added to a suspension of lithium aluminum hydride (94.7 mmol) in tetrahydrofuran (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was diluted with water (3.6 mL) and 15percentsodium hydroxide (10.8 mL) and the insoluble solids were removed by filtration. The aqueous layer was extracted with ethyl acetate (2 x 100 mL) and the combined organic layers were dried (sodium sulfate) and concentrated to provide 3,4-dihydro-2H- benzo[b][l,4]oxazine in 79percent yield as red oil. |
79% | With lithium aluminium tetrahydride In tetrahydrofuran for 16 h; Reflux | A solution of 2H-benzo[b][1,4]oxazin-3(4H)-one (38.2 mmol) in tetrahydrofuran (21 mL) was slowly added to a suspension of lithium aluminum hydride (94.7 mmol) in tetrahydrofuran (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was diluted with water (3.6 mL) and 15percent sodium hydroxide (10.8 mL) and the insoluble solids were removed by filtration. The aqueous layer was extracted with ethyl acetate (2.x.100 mL) and the combined organic layers were dried (sodium sulfate) and concentrated to provide 3,4-dihydro-2H-benzo[b][1,4]oxazine in 79percent yield as red oil. |
79% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 16 h; Reflux Stage #2: With water In tetrahydrofuran |
Intermediate 31: Synthesis of 4-methyl-3,4-dihydro-2H-benzo[b][l,4]oxazine-6-sulfonyl chloride.1. Synthesis of 3,4-dihvdro-2i/-benzo|'b][l,4"|oxazine.A solution of 2H-benzo[b][l,4]oxazin-3(4H)-one (38.2 mmol) in tetrahydrofuran (21 mL) was slowly added to a suspension of lithium aluminum hydride (94.7 mmol) in tetrahydrofuran (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was diluted with water (3.6 mL) and 15percentsodium hydroxide (10.8 mL) and the insoluble solids were removed by filtration. The aqueous layer was extracted with ethyl acetate (2 x 100 mL) and the combined organic layers were dried (sodium sulfate) and concentrated to provide 3,4-dihydro-2H- benzo[b][l,4]oxazine in 79percent yield as red oil. |
79% | With lithium aluminium tetrahydride In tetrahydrofuran for 16 h; Reflux | A solution of 2H-benzo[b][1,4]oxazin-3(4H)-one (38.2 mmol) in tetrahydrofuran (21 mL) was slowly added to a suspension of lithium aluminum hydride (94.7 mmol) in tetrahydrofuran (80 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was diluted with water (3.6 mL) and 15percent sodium hydroxide (10.8 mL) and the insoluble solids were removed by filtration. The aqueous layer was extracted with ethyl acetate (2*100 mL) and the combined organic layers were dried (sodium sulfate) and concentrated to provide 3,4-dihydro-2H-benzo[b][1,4]oxazine in 79percent yield as red oil. |
79% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuranHeating / reflux Stage #2: With sodium hydroxide; water In tetrahydrofuran |
Into a 250 mL 3-necked round bottom flask was placed a solution of lithium aluminum hydride (3.6 g, 94.74 mmol) in tetrahydrofuran (80 mL). The mixture was stirred for 15 minutes. This was followed by the addition of a solution of 2H-benzo[b][l,4]oxazin-3(4H)-one (5.7 g, 38.22 mmol) in tetrahydrofuran (21 mL), which was added drop wise with stirring. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux in a bath of <n="132"/>oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether = 1:1). The reaction mixture was then quenched by the adding 3.6 mL of H2O and 10.8 mL 15percentNaOH. A filtration was performed. The filter cake was washed with 30 mL of tetrahydrofuran. The resulting solution was extracted two times with 100 mL of ethyl acetate and the organic layers combined and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 4.8 g (79percent) of 3,4-dihydro-2H-benzo[b]fl,4]oxazine as red oil. |
72% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16 h; | General procedure: LAH (2 equiv.) in THF (100 mL) was cooled to 0oC inan ice bath under nitrogen. A solution of 4 (1 equiv.) in THF (20 mL) was added dropwise, and the resulting solution was stirred at RT for 16 hrs. The reaction mixture was cooled to 0oC andcarefully quenched with water (2 mL), 2 N NaOH (2 mL) and water (8 mL). The resulting slurrywas stirred at RT for 1 h and filtered through Celite. The filter cake was washed with ethylacetate and discarded. The filtrate was dried (Na2SO4), separated and concentrated to afford 5 asa colorless oil. |
50% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Reflux Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0℃; |
Step B: 3,4-Dihydro-2H-benzo[l,4]oxazine. To a mixture of LAH (3.6 g, 94.74 mmol) in THF (80 ml) was added a solution of 4H-Benzo[l,4]oxazin-3-one (5.7 g, 38.22 mmol) in THF (21 ml) dropwise at room temperature. The reaction mixture was refluxed overnight. The resulting mixture was cooled to 0°C and then quenched by the adding 3.6 ml of H20, followed by 10.8 ml 15percent NaOH solution. The precipitate was filtered off and the solvent was extracted with EtOAc (2x50 ml). The organic layer was washed with brine, dried over Na2S04, filtered and concentrated to give the 3,4-dihydro-2H-benzo[b][l,4]oxazine as red oil which was pure enough to be used directly (1.5 g , 50percent yield). 1H NMR (300 MHz, DMSO-d6): δ 6.67-6.41 (m, 4H), 5.68 (s, 1H), 4.11-4.07 (m, 2H), 3.27-3.24 (m, 2H). |
4.3 g | With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 16 h; Inert atmosphere; Reflux | Synthesis of 3,4-dihydro-2H-1,4-benzoxazine (Intermediate-29) A solution of Starting Material-13(5 g, 33.5 mmol) in tetrahydrofuran (50 mL) was slowly added to a suspension of lithium aluminum hydride (3.18 g, 83.8 mmol) under N2 atmosphere at 0° C. The reaction mixture was refluxed for 16 h. The reaction mixture was diluted with EtOAc, quenched with 15percent aqueous sodium hydroxide solution at 0° C., and extracted with ether, and concentrated to give Intermediate-29 as brown liquid (4.3 g). |
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