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[ CAS No. 111141-00-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 111141-00-5
Chemical Structure| 111141-00-5
Structure of 111141-00-5 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 111141-00-5 ]

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Product Details of [ 111141-00-5 ]

CAS No. :111141-00-5 MDL No. :MFCD09744011
Formula : C9H7FO2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :FKDMFDMYQZIZMI-UHFFFAOYSA-N
M.W : 166.15 Pubchem ID :13953817
Synonyms :

Calculated chemistry of [ 111141-00-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.97
TPSA : 26.3 ?2

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) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 1.48
Log Po/w (WLOGP) : 2.21
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : 2.83
Consensus Log Po/w : 1.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.12 mg/ml ; 0.00672 mol/l
Class : Soluble
Log S (Ali) : -1.64
Solubility : 3.81 mg/ml ; 0.0229 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.13
Solubility : 0.124 mg/ml ; 0.000745 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 111141-00-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 111141-00-5 ]

* 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 [ 111141-00-5 ]

[ 111141-00-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 151-50-8 ]
  • [ 111141-00-5 ]
  • [ 111140-49-9 ]
  • 2
  • [ 2967-72-8 ]
  • [ 111141-00-5 ]
YieldReaction ConditionsOperation in experiment
98% 8-Fluorochroman-4-one. Oxalyl chloride (8.79 mL) and 1 drop of DMF were added to an ice cold solution of 3-(2-fluororhohenoxy)propanoic acid (9.27 g) in DCM (50 mL). The solution was stirred at 0 C for 2 hours, then aluminum chloride (7.39g, 55.42mM) was added and the solution was stirred for 16 hours at room temperature. The mixture was poured onto ice water, and extracted three times with DCM. The combined organics were washed with 0.5M NaOH and brine, then dried, evaporated, and purified by column chromatography (eluting with 20% EtOAc/Hex) to give of the title compound (8.2Og, 98%).
98% 8-fluorochroman-4-one (37). Oxalyl chloride (8.79 mL) and one drop of DMF were added to an ice cold solution of 3-(2-fluorophenoxy)propanoic acid (9.27 g) in DCM (50 mL). The solution was stirred at 0 C. for two hours, aluminum chloride (7.39 g, 55.42 mM) was added and the solution was stirred for 16 hours at RT. The mixture was poured onto ice water, and extracted three times with DCM. The combined organics were washed with 0.5M NaOH and brine, dried, evaporated, and purified by column chromatography (eluding with 20% EtOAc/Hex) to give 8-fluorochroman-4-one (37) (8.20 g, 98%). 8-Fluorochroman-4-one. Oxalyl chloride (8.79 mL) and 1 drop of DMF were added to an ice cold solution of 3-(2-fluorophenoxy)propanoic acid (9.27 g) in DCM (50 mL). The solution was stirred at 0 C. for 2 hours, then aluminum chloride (7.39 g, 55.42 mM) was added and the solution was stirred for 16 hours at room temperature. The mixture was poured onto ice water, and extracted three times with DCM. The combined organics were washed with 0.5M NaOH and brine, then dried, evaporated, and purified by column chromatography (eluting with 20% EtOAc/Hex) to give of the title compound (8.20 g, 98%).
53% With polyphosphoric acid; at 100℃; for 2h; A mixture of compound (174a) (3.7 g, 20.3 mmol) in polyphosphoric acid (59.5 g, 607.6 mmol) was stirred at 100 C for 2 hours. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was triturated in diethyl ether and filtered. The filtrate was concentrated to provide compound (174b) (1.80 g, 10.8 mmol, 53%) which was used without further purification. 1H NMR (300 MHz, CDCl3) delta 2.83-2.90 (m, 2H), 4.60-4.68 (m, 2H), 6.95 (td, J = 8.0/4.4 Hz, 1H), 7.30 (ddd, J = 1.4/8.0/10.6 Hz, 1H), 7.67 (td, J = 1.4/8.0 Hz, 1H). MS m/z ([M+H]+) 167.
With polyphosphoric acid; at 100℃; for 3.5h; Polyphosphoric acid (7.0 g) was added to the compound 1-2 (450 mg) , and the mixture was stirred at 100C for 3.5 hours. The heat source was turned off and the temperature was lowered to 75C. At that time, crushed ice was gradually added to the reaction mixture with vigorous stirring. When the temperature was returned to room temperature, the reaction solution was added to ice water. The aqueous layer was extracted with diethyl ether, and the organic layer was sequentially washed with aqueous sodium bicarbonate and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (273 mg) .IH NMR (400 MHz, CDCl3) (ppm) : 2.89 (t, J=6.4 Hz, 2H), 4.66 (t, J=6.4 HZ, 2H), 6.98 (td, J=4.4 , 8.0 Hz, IH), 7.29-7.34 (m, IH), 7.71 (dt, J=I.5, 8.0 Hz, IH)

  • 3
  • 3-(2-fluorophenoxy)propanoic acid chloride [ No CAS ]
  • [ 111141-00-5 ]
YieldReaction ConditionsOperation in experiment
98% With aluminum (III) chloride; In dichloromethane; at 20℃; for 16h; 8-Fluorochroman-4-one. Oxalyl chloride (8.79 mL) and 1 drop of DMF were added to an ice cold solution of 3-(2-fluorophenoxy)propanoic acid (9.27 g) in DCM (50 mL). The solution was stirred at 0 C. for 2 hours, then aluminum chloride (7.39 g, 55.42 mM) was added and the solution was stirred for 16 hours at room temperature. The mixture was poured onto ice water, and extracted three times with DCM. The combined organics were washed with 0.5M NaOH and brine, then dried, evaporated, and purified by column chromatography (eluding with 20% EtOAc/Hex) to give of the title compound (8.20 g, 98%).
aluminum (III) chloride; In dichloromethane; at 20℃; for 16h; Oxalyl chloride (8.79 mL) and one drop of DMF were added to an ice cold solution of 3-(2-fluorophenoxy)propanoic acid (9.27 g) in DCM (50 mL). The solution was stirred at 0 0C for two hours, aluminum chloride (7.39g, 55.42mM) was added and the solution was stirred for 16 hours at RT. The mixture was poured onto ice water, and extracted three times with DCM. The combined organics were washed with 0.5M NaOH and brine, dried, evaporated, and purified by column <n="36"/>chromatography (eluting with 20% EtOAc/Hex) to give 8-fluorochroman-4-one (37) (8.2Og, 98%),
  • 4
  • [ 111140-91-1 ]
  • [ 111141-00-5 ]
  • 5
  • [ 111141-00-5 ]
  • 8-fluoro-4-methylenechromane [ No CAS ]
  • 6
  • [ 111141-00-5 ]
  • 8-fluorochroman-4-one oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium acetate; In ethanol; for 18h;Heating / reflux; 8-Fluorochroman-4-amine.; A round bottom flask was charged with <strong>[111141-00-5]8-fluorochroman-4-one</strong> (8.2 g), hydroxylamine hydrochloride (3.78 g) and sodium acetate (4.46 g). A reflux condenser was added, the flask was purged with argon, dry EtOH (20 mL) was added, and the mixture was stirred at reflux for 18 hours. The solution was cooled to room temperature, diluted with EtOAc, and washed with water. The organic phase was dried, and evaporated to give the intermediate <strong>[111141-00-5]8-fluorochroman-4-one</strong> oxime, which was reduced with Raney Nickel in EtOH at 50 PSI to yield the titled amine (4.69 g, 57%).
With hydroxylamine hydrochloride; sodium acetate; In ethanol; for 18h;Heating / reflux; 8-Fluorochroman-4-amine. A round bottom flask was charged with 8- fluorochroman-4-one (8.2g), hydroxylamine hydrochloride (3.78g) and sodium acetate (4.46g). A reflux condenser was added, the flask was purged with argon, dry EtOH (20 mL) was added, and the mixture was stirred at reflux for 18 hours. The solution was cooled to room temperature, diluted with EtOAc, and washed with water. The organic phase was dried, and evaporated to give the intermediate 8-fluorochroman-4- one oxime, which was reduced with Raney Nickel in EtOH at 50 PSI to yield the titled amine (4.69g, 57%). EPO <DP n="99"/>
With hydroxylamine hydrochloride; sodium acetate; In ethanol; for 18h;Heating / reflux; 8-fluorochroman-4-amine (39). A round bottom flask was charged with <strong>[111141-00-5]8-fluorochroman-4-one</strong> (8.2 g), hydroxylamine hydrochloride (3.78 g) and sodium acetate (4.46 g). A reflux condenser was added, the flask was purged with argon, dry EtOH (20 mL) was added, and the mixture was stirred at reflux for 18 hours. The solution was cooled to RT, diluted with EtOAc, and washed with water. The organic phase was dried, and evaporated to give the intermediate <strong>[111141-00-5]8-fluorochroman-4-one</strong> oxime (38), which was reduced with Raney Nickel in EtOH at 50 PSI to yield the titled amine (39) (4.69 g, 57%).; 8-Fluorochroman-4-amine. A round bottom flask was charged with <strong>[111141-00-5]8-fluorochroman-4-one</strong> (8.2 g), hydroxylamine hydrochloride (3.78 g) and sodium acetate (4.46 g). A reflux condenser was added, the flask was purged with argon, dry EtOH (20 mL) was added, and the mixture was stirred at reflux for 18 hours. The solution was cooled to room temperature, diluted with EtOAc, and washed with water. The organic phase was dried, and evaporated to give the intermediate <strong>[111141-00-5]8-fluorochroman-4-one</strong> oxime, which was reduced with Raney Nickel in EtOH at 50 PSI to yield the titled amine (4.69 g, 57%).
With hydroxylamine hydrochloride; sodium acetate; In ethanol; for 18h;Heating / reflux; A round bottom flask was charged with 8- fluorochroman-4-one (8.2g), hydro xylamine hydrochloride (3.78g) and sodium acetate (4.46g). A reflux condenser was added, the flask was purged with argon, dry EtOH (20 mL) was added, and the mixture was stirred at reflux for 18 hours. The solution was cooled to RT, diluted with EtOAc, and washed with water. The organic phase was dried, and evaporated to give the intermediate <strong>[111141-00-5]8-fluorochroman-4-one</strong> oxime (38), which was reduced with Raney Nickel in EtOH at 50 PSI to yield the titled amine (39) (4.69g, 57%).

  • 7
  • [ 111141-00-5 ]
  • [ 113209-68-0 ]
  • [ 917248-49-8 ]
  • [ 1092938-99-2 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 18h; At a temperature of 0 0C, sodium borohydride (7.4 g, 195 mmol) was added portion-wise to a mixture of 7-fluoro-2,3-dihydro-4/-/-chromen-4-one and 8-fluoro-2,3-dihydro-4/-/-chromen-4-one (16.2 g, 97.5 mmol) in methanol (200 ml). After a period of 1 hour at 0 0C and 17 hours at room temperature, the reaction mixture was quenched with saturated ammonium chloride solution (400 ml) and water (200 ml), and extracted with dichloromethane (2 x). The combined organic phases were washed with water and saturated sodium chloride solution, dried over magnesium sulfate, and the solvent was evaporated. The yellow residue crystallized slowly. The title compound was isolated as mixture with 8- fluorochroman-4-ol (16.28 g, 99 % yield).
  • 8
  • [ 133077-42-6 ]
  • [ 111141-00-5 ]
  • [ 113209-68-0 ]
YieldReaction ConditionsOperation in experiment
A solution of 3-(3-fluorophenoxy)propanoic acid (20.0 g, 108 mmol) in toluene (230 ml) and thionyl chloride (64.3 g, 0.54 mol) was refluxed for 17 hours. The reaction mixture was concentrated several times in the presence of toluene. A solution of the yellow oily residue in chloroform (200 ml) was cooled to -65 0C and treated with trifluoromethanesulfonic acid (48.0 ml, 0.54 mol, addition over 45 min). The brown solution was gradually warmed to room temperature. After a period of 17 h, the reaction mixture was poured on ice water (1 I) and the phases were separated. The aqueous phase was extracted with chloroform (200 ml). The combined organic phases were washed with 1 N sodium hydroxide solution (2 x 200 ml), water, and saturated sodium chloride solution, and dried over magnei- sum sulfate. Evaporation of the solvent afforded the title compound as mixture with 8-fluoro-2,3- dihydro-4/-/-chromen-4-one (16.26 g of a yellow solid, 91 % yield).
  • 9
  • [ 4071-88-9 ]
  • [ 111141-00-5 ]
  • [ 1206837-17-3 ]
YieldReaction ConditionsOperation in experiment
A solution of N-butyllithium in hexane (1.6 N, 1.88 ml) was added to a solution of dicyclohexylamine (545.7 mg) in tetrahydrofuran (13.0 ml) , cooled to -78C in a dry ice-acetone bath. After stirring at the same temperature for 10 minutes, a solution of ethyl (trimethylsilyl) acetate (482.3 mg) in tetrahydrofuran (2.5 ml) was added. After stirring at -78C for 10 minutes, a solution of the compound 4-1 (250.0 mg) in tetrahydrofuran (2.5 ml) was added. The mixture was stirred at -78C for one hour, and then returned to room temperature and further stirred for three hours. After confirming disappearance of the raw material, the reaction mixture was added to brine. The aqueous layer was extracted with ethyl acetate . The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain the title compound (162 mg) . 1H NMR (400 MHz, CDCl3) (ppm) : 1.29 (t, J=7.1 Hz, 3H), 2.67 (td, J=I.3, 5.9 Hz, 2H), 4.22 (q, J=7.1 Hz, 2H), 4.44-4.49 (m, 2H), 5.76 (s, IH), 6.78 (td, J=5.1, 8.1 Hz, IH), 7.06 (ddd, J=I.5, 8.1, 10.9 Hz, IH), 7.57 (dt, J=I.5, 8.1 Hz, IH)
  • 10
  • [ 111141-00-5 ]
  • [ 1018978-81-8 ]
  • 11
  • [ 111141-00-5 ]
  • [ 74-95-3 ]
  • 8-fluoro-4-methylenechromane [ No CAS ]
  • 12
  • [ 1421130-32-6 ]
  • [ 111141-00-5 ]
  • [ 1421064-47-2 ]
  • [ 1421064-97-2 ]
YieldReaction ConditionsOperation in experiment
With tetrabutoxytitanium; sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine; In methanol; at 20℃; for 14h; Example 148C[(2R,3aR,6aR)-2- [(4R)-8-fluoro-3,4-dihydro-2H-chromen-4- yl]amino } hexahydropentalen-3 a( 1 H)-yl] [3 -(trifluoromethyl)-7, 8-dihydro- 1 ,6- naphthyridin-6(5H)-yl]methanoneA mixture of Example 148B (85.1 mg, 0.51 mmol) and Example 79N (0.2 g, 0.51 mol) in Ti-(OiPr)4 (5 mL) was added N,N-diisopropylethylamine (0.196 g, 1.53 mmol) dropwise at room temperature. The mixture was stirred at room temperature for 12 hours. NaBH4 (0.197 g, 5.1 mmol) was added to the reaction mixture, followed by addition of methanol (10 mL) and stirred for 2 hours at room temperature. LC-MS indicated that the reaction was complete, the mixture was washed with aqueous NaHC(? (15 mL), the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The organic layer was dried over Na2S04,concentrated in vacuum and purified by chromatography on silica and then SFC (Instrument: Berger MultiGram SFC, Mettler Toledo Co, Ltd; Column: Chiralcel OJ 250x30 mm ID, 5 muiotaeta; Mobile phase: A: Supercritical CO2, B: isopropanol (0.05% diethylamine as modifier), A:B =70:30 at 60 mL/min; Column Temp: 38 C; Nozzle Pressure: 100 Bar; Nozzle Temp: 60 C; Evaporator Temp: 20 C Trimmer Temp: 25 C; Flow rate: 60 mL/min; Wavelength: 220 nm.) to afford the title compound as a white solid (peak 1, retention time 6.5 minute, 2.31 mg), as well as Example 201 (peak 2, retention time 7.22 minute, 0.98 mg). NMR (400 MHz, CD3OD): delta 8.68 (s, 1H), 8.04 (s, 1H), 6.95 (m, 3H), 4.70 (m, 2H), 4.25 (m, 2H), 4.31 (m, 1H), 3.95 (m, 3H), 3.51 (m, 2H), 3.10 (m, 2H), 2.29 (m, 1H), 1.90 (m, 9H), 1.55 (m, 1H), 1.31 (m, 2H); MS (ESI) m/z 503 (M+H)+.
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