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[ CAS No. 881189-74-8 ] {[proInfo.proName]}

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Chemical Structure| 881189-74-8
Chemical Structure| 881189-74-8
Structure of 881189-74-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 881189-74-8 ]

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Product Details of [ 881189-74-8 ]

CAS No. :881189-74-8 MDL No. :MFCD14654077
Formula : C9H6BrFO Boiling Point : No data available
Linear Structure Formula :- InChI Key :FVPXVDTWEBFLLE-UHFFFAOYSA-N
M.W : 229.05 Pubchem ID :50989426
Synonyms :

Calculated chemistry of [ 881189-74-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.15
TPSA : 17.07 ?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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 3.14
Log Po/w (MLOGP) : 2.84
Log Po/w (SILICOS-IT) : 3.82
Consensus Log Po/w : 2.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.151 mg/ml ; 0.000661 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.79 mg/ml ; 0.00345 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.25
Solubility : 0.0127 mg/ml ; 0.0000556 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 881189-74-8 ]

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

Application In Synthesis of [ 881189-74-8 ]

* 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 [ 881189-74-8 ]

[ 881189-74-8 ] Synthesis Path-Downstream   1~12

  • 2
  • [ 881189-74-8 ]
  • [ 1400702-00-2 ]
YieldReaction ConditionsOperation in experiment
With triethylsilane; trifluoroacetic acid; at 20℃; To a solution of 6-bromo-4-fluoroindan-l-one (57 mg, 0.26 mmol) in trifluoroacetic acid (1.1 mL) was added triethylsilane (103 ih, 0.65 mmol), and the mixture was stirred at room temperature overnight. The reaction solution was poured into ice water, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, washed with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was filtered through Phase-separator (Varian Inc.), and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 100:0) to give a crude 6-bromo-4-fluoroindane (61 mg) as a yellow oil. The resultant was used in the next step without further purification.
  • 3
  • [ 881189-74-8 ]
  • [ 1593700-28-7 ]
  • [ 1593697-33-6 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 85℃; for 3h;Inert atmosphere; Alternative Preparation of (R)-3-[6-(2-Cyclopropyl-ethoxy)-pyridin-3-yloxv]-1-(7-fluoro-3-oxo-indan-5-yl)-pyrrolidin-2-one (Example 1-08) A mixture of (R)-3-[6-(2-cyclopropyl-ethoxy)-pyridin-3-yloxy]-pyrrolidin-2-one (100 mg), <strong>[881189-74-8]6-bromo-4-fluoro-2,3-dihydro-1H-inden-1-one</strong> (87 mg) and 1,4-dioxane (2 mL) was purged with argon. N,N'-Dimethyl-ethylene-diamine (336 mg), cesium carbonate (248 mg) and copper(I) iodide (7 mg) were added. The mixture was heated to 85 C. for 3 hours. After cooling to r.t. the mixture was filtered and the filtrate purified by preparative HPLC to provide Example 1-08. 1H-NMR (400 MHz, DMSO) 67.99 (1H, dd, J=11.3, 1.8 Hz), 7.97 (1H, d, J=3.1 Hz), 7.77 (1H, d, J=1.8 Hz), 7.53 (1H, dd, J=9.0, 3.1 Hz), 6.77 (1H, d, J=9.0 Hz), 5.22 (1H, dd, J=8.3, 8.3 Hz), 4.24 (2H, t, J=6.8 Hz), 3.96 (1H, m), 3.86 (1H, m), 3.10 (2H, m), 2.72 (2H, m), 2.69 (1H, m), 2.14 (1H, m), 1.60 (2H, dt, J=6.8, 6.8 Hz), 0.80 (1H, m), 0.42 (2H, m), 0.10 (2H, m).
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 85℃; for 3h;Inert atmosphere; A mixture of (R)-3-[6-(2-cyclopropyl-ethoxy)-pyridin-3-yloxy]-pyrrolidin-2-one (100 mg), 6-bromo-4-fluoro-2,3-dihydro-1 H-inden-1 -one (87 mg) and 1 ,4-dioxane (2 mL) was purged with argon. Lambda/,Lambda/'-Dimethyl-ethylene-diamine (336 mg), cesium carbonate (248 mg) and copper(l) iodide (7 mg) were added. The mixture was heated to 85C for 3 hours. After cooling to r.t. the mixture was filtered and the filtrate purified by preparative HPLC to provide Example 1 -08. 1H-NMR (400 MHz, DMSO) 5 7.99 (1 H, dd, J = 1 1 .3, 1 .8 Hz), 7.97 (1 H, d, J = 3.1 Hz), 7.77 (1 H, d, J= 1 .8 Hz), 7.53 (1 H, dd, J= 9.0, 3.1 Hz), 6.77 (1 H, d, J = 9.0 Hz), 5.22 (1 H, dd, J = 8.3, 8.3 Hz), 4.24 (2H, t, J = 6.8 Hz), 3.96 (1 H, m), 3.86 (1 H, m), 3.10 (2H, m), 2.72 (2H, m), 2.69 (1 H, m), 2.14 (1 H, m), 1 .60 (2H, dt, J = 6.8, 6.8 Hz), 0.80 (1 H, m), 0.42 (2H, m), 0.10 (2H, m).
  • 4
  • [ 881189-74-8 ]
  • [ 1593699-48-9 ]
  • 5
  • [ 881189-74-8 ]
  • [ 1593701-18-8 ]
  • [ 1593697-75-6 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 1.5h;Inert atmosphere; Alternative Preparation of (R)-3-(6-Ethoxy-pyridin-3-yloxy)-1-(7-fluoro-3-oxo-indan-5-yl)-pyrrolidin-2-one (Example 2-08) To a mixture of (R)-1-(7-fluoro-3-oxo-indan-5-yl)-3-(6-hydroxy-pyridin-3-yloxy)-pyrrolidin-2-one (60 mg), ethanol (23 mg) and solvent (THF/DCM/NMP 4:4:1, 5 mL) under argon was added triphenylphosphine (polymer, 0.4 mmol). After 5 minutes DIAD (51 mg) was added. The mixture was shaken at 40 C. for 12 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by preparative HPLC to provide Example 2-08. In a further alternative preparation a mixture of (R)-3-((6-ethoxypyridin-3-yl)oxy)pyrrolidin-2-one (2.00 g), <strong>[881189-74-8]6-bromo-4-fluoro-2,3-dihydro-1H-inden-1-one</strong> (2.30 g), N,N'-dimethyl-ethylene-diamine (10 mL) and 1,4-dioxane (20 mL) was purged with argon and cesium carbonate (3.8 g) and copper(I) iodide (100 mg) were added. The mixture was heated to 100 C. for 1.5 hours. After cooling to r.t. the mixture was diluted with EA and washed with water (5 times) and brine. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by SGC (eluent: heptane with 0 to 70% EA) to provide Example 2-08. 1H-NMR (400 MHz, DMSO) delta 7.99 (1H, dd, J=11.3, 1.8 Hz), 7.97 (1H, d, J=3.1 Hz), 7.77 (1H, d, J=1.8 Hz), 7.53 (1H, dd, J=8.9, 3.1 Hz), 6.76 (1H, d, J=8.9 Hz), 5.22 (1H, dd, J=8.3, 8.3 Hz), 4.24 (2H, q, J=7.0 Hz), 3.96 (1H, m), 3.86 (1H, m), 3.11 (2H, m), 2.72 (2H, m), 2.69 (1H, m), 2.13 (1H, m), 1.30 (3H, t, J=7.0 Hz).
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 1.5h;Inert atmosphere; In a further alternative preparation a mixture of (R)-3-((6-ethoxypyridin-3- yl)oxy)pyrrolidin-2-one (2.00 g), 6-bromo-4-fluoro-2,3-dihydro-1 H-inden-1 -one (2.30 g), Lambda/,Lambda/'-dimethyl-ethylene-diamine (10 mL) and 1 ,4-dioxane (20 mL) was purged with argon and cesium carbonate (3.8 g) and copper(l) iodide (100 mg) were added. The mixture was heated to 100C for 1 .5 hours. After cooling to r.t. the mixture was diluted with EA and washed with water (5 times) and brine. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by SGC (eluent: heptane with 0 to 70% EA) to provide Example 2-08. 1H-NMR (400 MHz, DMSO) delta 7.99 (1 H, dd, J = 1 1 .3, 1 .8 Hz), 7.97 (1 H, d, J = 3.1 Hz), 7.77 (1 H, d, J = 1 .8 Hz), 7.53 (1 H, dd, J = 8.9, 3.1 Hz), 6.76 (1 H, d, J = 8.9 Hz), 5.22 (1 H, dd, J = 8.3, 8.3 Hz), 4.24 (2H, q, J = 7.0 Hz), 3.96 (1 H, m), 3.86 (1 H, m), 3.1 1 (2H, m), 2.72 (2H, m), 2.69 (1 H, m), 2.13 (1 H, m), 1 .30 (3H, t, J = 7.0 Hz).
  • 6
  • [ 881189-74-8 ]
  • [ 1593700-31-2 ]
  • [ 1593697-39-2 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 80℃; for 4h;Inert atmosphere; Alternative Preparation of (R)-3-(6-Cyclopropylmethoxy-pyridin-3-yloxy)-1-(7-fluoro-3-oxo-indan-5-yl)-pyrrolidin-2-one (Example 1-11) A mixture of (R)-3-[6-(2-cyclopropyl-methoxy)-pyridin-3-yloxy]-pyrrolidin-2-one (100 mg), <strong>[881189-74-8]6-bromo-4-fluoro-2,3-dihydro-1H-inden-1-one</strong> (92 mg) and 1,4-dioxane (2 mL) was purged with argon. N,N'-Dimethyl-ethylene-diamine (355 mg), cesium carbonate (263 mg) and copper(I) iodide (8 mg) were added. The mixture was heated to 80 C. for 4 hours. After cooling to r.t. the mixture was filtered and the filtrate purified by preparative HPLC to provide Example 1-11. 1H-NMR (400 MHz, DMSO) delta 7.99 (1H, dd, J=11.2, 1.8 Hz), 7.95 (1H, d, J=3.1 Hz), 7.77 (1H, d, J=1.8 Hz), 7.53 (1H, dd, J=9.0, 3.1 Hz), 6.79 (1H, d, J=9.0 Hz), 5.22 (1H, dd, J=8.3, 8.3 Hz), 4.03 (2H, d, J=7.1 Hz), 3.96 (1H, m), 3.86 (1H, m), 3.10 (2H, m), 2.72 (2H, m), 2.68 (1H, m), 2.13 (1H, m), 1.22 (1H, m), 0.54 (2H, m), 0.30 (2H, m).
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 80℃; for 4h;Inert atmosphere; A mixture of (R)-3-[6-(2-cyclopropyl-methoxy)-pyridin-3-yloxy]-pyrrolidin-2-one (100 mg), 6-bromo-4-fluoro-2,3-dihydro-1 H-inden-1 -one (92 mg) and 1 ,4-dioxane (2 mL) waspurged with argon. Lambda/,Lambda/'-Dinnethyl-ethylene-diannine (355 mg), cesium carbonate (263 mg) and copper(l) iodide (8 mg) were added. The mixture was heated to 80C for 4 hours. After cooling to r.t. the mixture was filtered and the filtrate purified by preparative HPLC to provide Example 1 -1 1 . 1 H-NMR (400 MHz, DMSO) 5 7.99 (1 H, dd, J = 1 1 .2, 1 .8 Hz), 7.95 (1 H, d, J = 3.1 Hz), 7.77 (1 H, d, J = 1 .8 Hz), 7.53 (1 H, dd, J = 9.0, 3.1 Hz), 6.79 (1 H, d, J = 9.0 Hz), 5.22 (1 H, dd, J = 8.3, 8.3 Hz), 4.03 (2H, d, J = 7.1 Hz), 3.96 (1 H, m), 3.86 (1 H, m), 3.10 (2H, m), 2.72 (2H, m), 2.68 (1 H, m), 2.13 (1 H, m), 1 .22 (1 H, m), 0.54 (2H, m), 0.30 (2H, m).
  • 7
  • [ 881189-74-8 ]
  • [ 1593700-31-2 ]
  • [ 1593699-97-8 ]
  • 8
  • [ 34368-52-0 ]
  • [ 881189-74-8 ]
  • [ 1593701-30-4 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 80℃; for 3h;Inert atmosphere; (S)-1-(7-Fluoro-3-oxo-indan-5-yl)-3-hydroxy-pyrrolidin-2-one A mixture of <strong>[881189-74-8]6-bromo-4-fluoro-indan-1-one</strong> (Enamine, 453 mg), (S)-3-hydroxy-pyrrolidin-2-one (200 mg) and 1,4-dioxane (3 mL) was purged with argon. Cesium carbonate (645 mg), N,N'-dimethyl-ethylene-diamine (2.24 mL) and copper(I) iodide (38 mg) were added and the mixture was heated to 80° C. for 3 hours. After cooling to r.t. the mixture was filtered and the filtrate evaporated. The residue was purified by SGC (eluent: heptane/EA 1:1 with 0 to 20percent MeOH) to provide the title compound. MS ESI+: m/z=250 [M+H]+.
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 80℃; for 3h;Inert atmosphere; A mixture of 6-bromo-4-fluoro-indan-1 -one (Enamine, 453 mg), (S)-3-hydroxy-pyrrolidin- 2-one (200 mg) and 1 ,4-dioxane (3 mL) was purged with argon. Cesium carbonate (645 mg), Lambda/,Lambda/'-dimethyl-ethylene-diamine (2.24 mL) and copper(l) iodide (38 mg) were added and the mixture was heated to 80°C for 3 hours. After cooling to r.t. the mixture was filtered and the filtrate evaporated. The residue was purified by SGC (eluent: heptane/EA 1 :1 with 0 to 20percent MeOH) to provide the title compound. MS ESI+: m/z = 250 [M+H]+.
  • 9
  • [ 881189-74-8 ]
  • [ 96-32-2 ]
  • methyl 2-(6-bromo-4-fluoro-1-oxo-2,3-dihydro-1H-inden-2-yl)acetate [ No CAS ]
  • (6-bromo-4-fluoro-2-methoxycarbonylmethyl-1-oxoindan-2-yl)acetic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Methyl 2-(6-bromo-4-fluoro-1 -oxo-2,3-dihydro-1 H-inden-2-yl)acetate To a mixture of diisopropylamine (1 .4 mL) and THF (25 mL) was added n-BuLi (3.4 mL, 2.6 M in toluene) at -78C. After 30 minutes a solution of 6-bromo-4-fluoro-2,3-dihydro- 1 H-inden-1 -one (2.0 g) in THF (10 mL) was added dropwise. After 30 minutes methyl 2- bromoacetate (1 .34 g) was added dropwise. The mixture was allowed to warm to RT with stirring for 2 hours. The mixture was poured into an ammonium chloride solution (10%, aqueous) and then extracted with EA (100 ml_ x 3). The organic phase was washed with brine and then dried over Na2SO4. The solvent was removed by evaporation under reduced pressure and the residue was purified by SGC (heptane to EA/heptane = 4:1 ) to provide the title compound. MS ESI+: m/z = 301 [M+H]+. As a second product (6-bromo-4-fluoro-2-methoxycarbonylmethyl-1 -oxo-indan-2-yl)-acetic acid methyl ester was isolated. MS ESI+: m/z = 373 [M+H]+.
  • 10
  • [ 881189-74-8 ]
  • 2-[6-[(3R)-3-[[6-(cyclopropylmethoxy)-3-pyridyl]oxy]-2-oxopyrrolidin-1-yl]-4-fluoro-2-(2-methoxy-2-oxoethyl)-1-oxoindan-2-yl]acetic acid [ No CAS ]
  • 11
  • [ 881189-74-8 ]
  • 6-bromo-4-fluoro-2-(2-hydroxyethyl)indan-1-ol [ No CAS ]
  • 12
  • [ 881189-74-8 ]
  • 6-bromo-4-fluoro-2-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-one [ No CAS ]
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Technical Information

? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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