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[ CAS No. 245762-35-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 245762-35-0
Chemical Structure| 245762-35-0
Chemical Structure| 245762-35-0
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Product Details of [ 245762-35-0 ]

CAS No. :245762-35-0 MDL No. :MFCD08236758
Formula : C8H7FO Boiling Point : -
Linear Structure Formula :- InChI Key :PAVTXINZFWRQOD-UHFFFAOYSA-N
M.W : 138.14 Pubchem ID :22398640
Synonyms :

Calculated chemistry of [ 245762-35-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.74
TPSA : 9.23 Ų

Pharmacokinetics

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) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 2.24
Log Po/w (WLOGP) : 2.18
Log Po/w (MLOGP) : 2.18
Log Po/w (SILICOS-IT) : 2.96
Consensus Log Po/w : 2.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.55
Solubility : 0.388 mg/ml ; 0.00281 mol/l
Class : Soluble
Log S (Ali) : -2.07
Solubility : 1.18 mg/ml ; 0.00852 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.159 mg/ml ; 0.00115 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 245762-35-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 245762-35-0 ]

* 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.

  • Downstream synthetic route of [ 245762-35-0 ]

[ 245762-35-0 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 24410-59-1 ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogen;palladium 10% on activated carbon; In acetic acid; under 2585.81 Torr; for 12h; A solution of <strong>[24410-59-1]5-fluorobenzofuran</strong> and 10% palladium on carbon in acetic acid (25 ml) was hydrogenated under 50 psi for 12 hours. The catalyst was filtered through celite and the celite was washed with methylene chloride (200 ml). The organic layer was washed sequentially with 1N NaOH (3 x 100 ml), brine (3 x 100 ml) and dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afforded 2.59 g (85%) of product as a clear oil: 1H NMR (300 MHz, CDCl3): delta 3.12 (t, 2H, J = 8.7 Hz), 4.58 (t, 2H, J = 8.7 Hz), 6.68 (dd, 1H, J = 8.7, 4.2 Hz), 6.79 (tm, 1H, J = 8.7 Hz), 6.89 (dm, 1H, J = 8.1 Hz).
  • 2
  • [ 4885-02-3 ]
  • [ 245762-35-0 ]
  • [ 245762-36-1 ]
YieldReaction ConditionsOperation in experiment
39% With titanium tetrachloride In dichloromethane at 0 - 20℃;
  • 3
  • [ 371-41-5 ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide / 0 °C 1.2: 80 percent / dimethylformamide / 18 h / 160 - 170 °C 2.1: 45 percent / polyphosphoric acid / benzene / 2.5 h / Heating 3.1: 85 percent / H2; AcOH / Pd/C / 12 h / 2585.74 Torr
  • 4
  • [ 59769-37-8 ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 45 percent / polyphosphoric acid / benzene / 2.5 h / Heating 2: 85 percent / H2; AcOH / Pd/C / 12 h / 2585.74 Torr
  • 5
  • [ 245762-35-0 ]
  • [ 245762-37-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 39 percent / TiCl4 / CH2Cl2 / 0 - 20 °C 2.1: 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide; m-CPBA / CH2Cl2 / 16 h / Heating 2.2: 50 percent / aq. NaOH / ethanol / 3 h / 20 °C
  • 6
  • [ 245762-35-0 ]
  • [ 245762-38-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 39 percent / TiCl4 / CH2Cl2 / 0 - 20 °C 2.1: 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide; m-CPBA / CH2Cl2 / 16 h / Heating 2.2: 50 percent / aq. NaOH / ethanol / 3 h / 20 °C 3.1: 97 percent / K2CO3 / butan-2-one / 24 h / Heating
  • 7
  • [ 245762-35-0 ]
  • [ 245762-40-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 39 percent / TiCl4 / CH2Cl2 / 0 - 20 °C 2.1: 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide; m-CPBA / CH2Cl2 / 16 h / Heating 2.2: 50 percent / aq. NaOH / ethanol / 3 h / 20 °C 3.1: 97 percent / K2CO3 / butan-2-one / 24 h / Heating 4.1: 95 percent / NaN3 / dimethylformamide / 24 h / 60 °C 5.1: 100 percent / Ph3P; H2O / tetrahydrofuran / 18 h / 20 °C
  • 8
  • [ 245762-35-0 ]
  • [ 245762-39-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 39 percent / TiCl4 / CH2Cl2 / 0 - 20 °C 2.1: 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide; m-CPBA / CH2Cl2 / 16 h / Heating 2.2: 50 percent / aq. NaOH / ethanol / 3 h / 20 °C 3.1: 97 percent / K2CO3 / butan-2-one / 24 h / Heating 4.1: 95 percent / NaN3 / dimethylformamide / 24 h / 60 °C
  • 9
  • [ 245762-35-0 ]
  • [2-(5-Fluoro-2,3-dihydro-benzofuran-7-yloxy)-ethyl]-[2-(5-fluoro-1H-indol-3-yl)-ethyl]-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 39 percent / TiCl4 / CH2Cl2 / 0 - 20 °C 2.1: 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide; m-CPBA / CH2Cl2 / 16 h / Heating 2.2: 50 percent / aq. NaOH / ethanol / 3 h / 20 °C 3.1: 97 percent / K2CO3 / butan-2-one / 24 h / Heating 4.1: 95 percent / NaN3 / dimethylformamide / 24 h / 60 °C 5.1: 100 percent / Ph3P; H2O / tetrahydrofuran / 18 h / 20 °C 6.1: 54 percent / Et3N / dimethylsulfoxide / 14 h / 90 °C
  • 10
  • [ 245762-35-0 ]
  • [ 282547-30-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: With nitric acid; acetic anhydride at 20℃; for 0.5h; Stage #2: 5-fluoro-2,3-dihydrobenzofuran at 10 - 20℃; for 2h; 17 INTERMEDIATE 17 5-Fluoro-7-nitro-2,3-dihydrobenzofuran A mixture of nitric acid (100%, 1.5 ml, 36 mmol) in acetic anhydride (18 ml) was maintained at room temperatue for 0.5 hour. The mixture was added to a solution of 5-fluoro-2,3-dihydrobenzofuran (2.5 g, 18 mmol) in 10 ml acetic anhydride at 10°C. The reaction mixture was stirred at room temperature for 2 hours then poured into ice-water. The mixture was extracted with methylene chloride (3 x 60 ml), washed with 1N sodium hydroxide (5 x 100 ml) and brine (200 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afford a yellow solid: mp 113-114°C.
  • 11
  • [ 217195-91-0 ]
  • [ 245762-35-0 ]
  • [ 887375-45-3 ]
YieldReaction ConditionsOperation in experiment
61.3% With aluminum (III) chloride In dichloromethane at 3 - 25℃; for 48.96 - 72.96h; 2 2) Synthesis of ethyl-4-(5-fluoro-2,3-dihydro-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoate; A solution of 0,07 mol 5-fluoro-2,3-dihydro-benzofurane in 21 ml of dichloromethan is cooled to 3°C. To this solution 0,1 mol of AlCl3 is added over a period of 30 minutes. After this addition 0,05 mol of ethyl-2-hydroxy-4-methyl-2-(trifluoromethyl)pentenoate is added dropwise over 30 minutes. The mixture is stirred for 2-3 days at 25°C. After complete reaction the solution is poured on a mixture of ice (50 ml) and 1M HCl (10 ml) and stirred for at least 1 hour. The aqueous phase is extracted three times with 51 ml of ethylacetate. The combined organic phases are washed with water, saturated sodium chloride solution (brine) and dried over magnesiumsulfate. The solvent is evaporated under vacuum. The product is recrystalized from n-heptane (product yield 61,3 %).
30% With aluminum (III) chloride In carbon disulfide at 20℃; for 72h; Inert atmosphere;
Stage #1: ethyl 2-hydroxy-4-methyl-2-(trifluoromethyl)-4-pentenoate; 5-fluoro-2,3-dihydrobenzofuran With aluminum (III) chloride at 0 - 20℃; for 7h; Stage #2: With water In ethyl acetate for 0.25h;
  • 12
  • 5-diazonium-2,3-dihydrobenzofuran tetrafluoroborate [ No CAS ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
45% In xylene for 1h; Heating / reflux; 23 A suspension of 9.7 g (41.46 mmol) of the above diazonium tetrafluoroborate salt in xylenes was warmed at reflux for 1 hour. The mixture was then cooled and diluted with 200 mL of saturated aqueous sodium bicarbonate. The aqueous was separated and extracted with three 50 mL portions of EtOAc. The combined organic layers were washed with 50 mL of aqueous sodium bicarbonate, 50 mL of brine, dried over magnesium sulfate, filtered, and concentrated to afford an oil. The crude oil was chromatographed on silica gel using EtOAc-hexanes (0: 100, then 0.5 : 99.5) to afford 2.6 g (45%) of the title compound.
  • 14
  • [ 496-16-2 ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; nitric acid / 3.5 h / 0 - 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 18 h / 20 °C / 3102.97 Torr 3.1: hydrogenchloride; tetrafluoroboric acid; sodium nitrite / water; tetrahydrofuran / -15 - 20 °C 3.2: 2 h / Reflux
  • 15
  • [ 17403-47-3 ]
  • [ 245762-35-0 ]
  • 17
  • [ 245762-35-0 ]
  • C8H13FO [ No CAS ]
  • C8H13FO [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.778 % de With C31H47ClNRu; hydrogen In hexane at 25℃; for 24h; Overall yield = 85 %; diastereoselective reaction;
  • 18
  • 1-bromo-5-fluoro-2-methoxy-3-methylbenzene [ No CAS ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
57% With palladium(0)bis(tricyclohexylphosphine); cesium pivalate In toluene at 140℃; for 16h; Inert atmosphere; Sealed tube; Glovebox;
  • 20
  • [ 1572185-50-2 ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetone 2: palladium(0)bis(tricyclohexylphosphine); cesium pivalate / toluene / 16 h / 140 °C / Inert atmosphere; Sealed tube; Glovebox
  • 21
  • mesityl boron dibromide [ No CAS ]
  • [ 245762-35-0 ]
  • C17H18BFO [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With C18H26Br2N2Ni; zinc In toluene at 60℃; for 24h; Inert atmosphere;
  • 22
  • [ 67-56-1 ]
  • [ 4151-77-3 ]
  • [ 245762-35-0 ]
  • C9H10BFO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: dibromo(phenyl)borane; 5-fluoro-2,3-dihydrobenzofuran With C18H26Br2N2Ni; zinc Stage #2: methanol
  • 23
  • [ 245762-35-0 ]
  • C8H8BFO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc; C18H26Br2N2Ni / toluene / 24 h / 60 °C / Inert atmosphere 2: methanol
  • 24
  • [ 245762-35-0 ]
  • C15H20BFO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc; C18H26Br2N2Ni 2: zinc(II) chloride
  • 25
  • [ 496-69-5 ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / ethanol / 16 h / Reflux 2: n-butyllithium / tetrahydrofuran / 2.08 h / Cooling with ice; Inert atmosphere
  • 26
  • [ 33513-42-7 ]
  • [ 245762-35-0 ]
  • 5-fluoro-2,3-dihydrobenzofuran-4-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
20 g Stage #1: 5-fluoro-2,3-dihydrobenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 1.16667h; Inert atmosphere; Stage #2: With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran for 0.166667h; Stage #3: N,N-dimethyl-formamide In tetrahydrofuran at -20℃; for 12h; 1.3; 3.3 Step 3: Preparation of 5-fluoro-2,3-dihydrobenzofuran-4-carbaldehyde (III-1) Under the protection of nitrogen, add 5-fluoro-2,3-dihydrobenzofuran (543mmol, 1.0eq) and tetrahydrofuran (1L) to a 2L single-necked round bottom flask at -78, and stir for 10min.Slowly add n-butyl lithium (654mmol, 1.2eq), continue to stir for 1h, then add TMEDA (817mmol, 1.5eq), stir for 10min,DMF (814mmol, 1.5eq) was added, the temperature was slowly raised to -20°C, and stirring was continued for 12h.TLC detection (developing solvent: petroleum ether/ethyl acetate = 10/1, Rf value: 0.5), there is a little raw material remaining. Under ice bath, quench with water, extract with ethyl acetate (500 mL*3), wash with saturated sodium chloride, combine the organic phases and dry with anhydrous magnesium sulfate.The solvent was removed by concentration under reduced pressure. After beating the crude product with petroleum ether, 20 g of compound III-1 was obtained as a white solid, and the yield was 24%.
  • 27
  • [ 922728-20-9 ]
  • [ 245762-35-0 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In tetrahydrofuran for 2.08333h; Cooling with ice; Inert atmosphere; 1.2; 3.2 Step 2: Preparation of 5-fluoro-2,3-dihydrobenzofuran (IV-1) In an ice bath, under a nitrogen atmosphere, add 2-bromo-1-(2-chloroethoxy)-4-fluorobenzene (V-1) (394mmol, 1.0eq) to a 2L single-necked round bottom flaskAnd anhydrous tetrahydrofuran (1L), stir for 5min.Add n-butyllithium (434mmol, 1.1eq), stir under ice bath for 2h.Stop stirring, TLC detected all the raw materials disappeared. Under ice bath, the reaction was quenched by adding saturated ammonium chloride solution, concentrated, extracted with ethyl acetate (500 mL*3), washed with saturated sodium chloride 3 times, combined the organic phases and dried over anhydrous magnesium sulfate.The solvent was removed by concentration, and the residue was distilled under reduced pressure with an oil pump to obtain 38 g of crude compound IV-1 as a colorless liquid with a yield rate of 70%.
  • 28
  • [ 245762-35-0 ]
  • 5-fluoro-2,3-dihydrobenzofuran-4-carbaldehyde oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere 1.2: 0.17 h 1.3: 12 h / -20 °C 2.1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 2 h / Reflux
  • 29
  • [ 245762-35-0 ]
  • (5-fluoro-2,3-dihydrobenzofuran-4-yl)methanamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere 1.2: 0.17 h 1.3: 12 h / -20 °C 2.1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 2 h / Reflux 3.1: acetic acid; zinc / 3 h / 20 °C 3.2: 2 h
  • 30
  • [ 245762-35-0 ]
  • [ 282547-31-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: HNO3 / 0.5 h / -10 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 25 °C
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