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Product Details of [ 63909-54-6 ]

CAS No. :63909-54-6 MDL No. :MFCD22574982
Formula : C11H16FO3P Boiling Point : -
Linear Structure Formula :- InChI Key :VLIMXNFVVHBLMJ-UHFFFAOYSA-N
M.W : 246.22 Pubchem ID :11207329
Synonyms :

Safety of [ 63909-54-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 63909-54-6 ]

* 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 [ 63909-54-6 ]

[ 63909-54-6 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 63909-54-6 ]
  • 2-fluorobenzylphosphono-5-sulphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfur trioxide at 0℃;
Multi-step reaction with 2 steps 1: concd HCl / Heating 2: SO3 / 0 °C
  • 4
  • [ 6515-21-5 ]
  • [ 63909-54-6 ]
  • [ 848487-67-2 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With 18-crown-6 ether; sodium methylate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 4-methoxymethoxy-benzaldehyde With 18-crown-6 ether In N,N-dimethyl-formamide at 20 - 120℃; for 6h;
  • 5
  • [ 13709-05-2 ]
  • [ 63909-54-6 ]
  • [ 848487-68-3 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With 18-crown-6 ether; sodium methylate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 3-methoxymethoxybenzaldehyde With 18-crown-6 ether In N,N-dimethyl-formamide at 20 - 120℃; for 6h;
  • 6
  • [ 5533-04-0 ]
  • [ 63909-54-6 ]
  • [ 848487-69-4 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With 18-crown-6 ether; sodium methylate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 2-(methoxymethoxy)benzaldehyde With 18-crown-6 ether In N,N-dimethyl-formamide at 20 - 120℃; for 6h;
  • 7
  • [ 446-48-0 ]
  • [ 122-52-1 ]
  • [ 63909-54-6 ]
YieldReaction ConditionsOperation in experiment
92% at 80℃; for 17h;
at 140℃;
at 87℃; Inert atmosphere; 6.1 Step 1: diethyl 2-fluorobenzylphosphonate Step 1: diethyl 2-fluorobenzylphosphonate[002051 A mixture of triethyl phosphite (5.73 g, 34.50 mmol) and 1-(bromomethyl)-2-fluorobenzene (5.67 g,30.00 mmol) was stirred under N2 at 87 °C overnight. The mixture was cooled to room temperature. Thereaction mixture was used directly for the next step without further operation.
  • 8
  • [ 63909-54-6 ]
  • [ 106-93-4 ]
  • [ 902526-57-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With n-butyllithium In n-heptane; toluene at -78℃; for 1h; Stage #2: ethylene dibromide In n-heptane; toluene at -78 - 20℃;
  • 9
  • [ 63909-54-6 ]
  • [3-(benzyloxy-formyl-amino)-1-(2-fluoro-phenyl)-propyl]-phosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: n-butyllithium / toluene; heptane / 1 h / -78 °C 1.2: toluene; heptane / -78 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 8 h / Heating 3.1: 70 percent / trifluoroacetic acid / CH2Cl2 / 8 h / 20 °C 4.1: 98 percent / tetrahydrofuran / 0 - 20 °C 5.1: Me3SiBr / CH2Cl2 / 0 - 20 °C 5.2: H2O / tetrahydrofuran / 0.08 h
  • 10
  • [ 63909-54-6 ]
  • [ 902526-66-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / toluene; heptane / 1 h / -78 °C 1.2: toluene; heptane / -78 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 8 h / Heating 3.1: 70 percent / trifluoroacetic acid / CH2Cl2 / 8 h / 20 °C 4.1: 98 percent / tetrahydrofuran / 0 - 20 °C
  • 11
  • [ 63909-54-6 ]
  • [ 902526-63-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / toluene; heptane / 1 h / -78 °C 1.2: toluene; heptane / -78 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 8 h / Heating 3.1: 70 percent / trifluoroacetic acid / CH2Cl2 / 8 h / 20 °C
  • 12
  • [ 63909-54-6 ]
  • [ 902526-60-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / toluene; heptane / 1 h / -78 °C 1.2: toluene; heptane / -78 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 8 h / Heating
  • 13
  • [ 63909-54-6 ]
  • 2,2-dimethyl-propionic acid (2,2-dimethyl-propionyloxymethoxy)-[1-(2-fluoro-phenyl)-3-(formyl-hydroxy-amino)-propyl]-phosphinoyloxymethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: n-butyllithium / toluene; heptane / 1 h / -78 °C 1.2: toluene; heptane / -78 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 8 h / Heating 3.1: 70 percent / trifluoroacetic acid / CH2Cl2 / 8 h / 20 °C 4.1: 98 percent / tetrahydrofuran / 0 - 20 °C 5.1: Me3SiBr / CH2Cl2 / 0 - 20 °C 5.2: H2O / tetrahydrofuran / 0.08 h 6.1: triethylamine / dimethylformamide / 20 - 70 °C 7.1: 84 percent / hydrogen / palladium on carbon / methanol / 1 h / 2250.18 Torr
  • 14
  • [ 63909-54-6 ]
  • [ 902526-70-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: n-butyllithium / toluene; heptane / 1 h / -78 °C 1.2: toluene; heptane / -78 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 8 h / Heating 3.1: 70 percent / trifluoroacetic acid / CH2Cl2 / 8 h / 20 °C 4.1: 98 percent / tetrahydrofuran / 0 - 20 °C 5.1: Me3SiBr / CH2Cl2 / 0 - 20 °C 5.2: H2O / tetrahydrofuran / 0.08 h 6.1: triethylamine / dimethylformamide / 20 - 70 °C
  • 15
  • [ 63909-54-6 ]
  • [ 89122-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOMe; 18/6-crown ether / dimethylformamide / 0.08 h / 20 °C 1.2: 95 percent / 18/6-crown ether / dimethylformamide / 6 h / 20 - 120 °C 2.1: 89 percent / pyridinium p-toluene sulfonate / methanol / Heating
  • 16
  • [ 63909-54-6 ]
  • (E)-1-hydroxy-4-(2-fluoro)styrylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOMe; 18/6-crown ether / dimethylformamide / 0.08 h / 20 °C 1.2: 90 percent / 18/6-crown ether / dimethylformamide / 6 h / 20 - 120 °C 2.1: 95 percent / pyridinium p-toluene sulfonate / methanol / Heating
  • 17
  • [ 63909-54-6 ]
  • 3-[(E)-2-(2-Fluoro-phenyl)-vinyl]-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOMe; 18/6-crown ether / dimethylformamide / 0.08 h / 20 °C 1.2: 96 percent / 18/6-crown ether / dimethylformamide / 6 h / 20 - 120 °C 2.1: 96 percent / pyridinium p-toluene sulfonate / methanol / Heating
  • 19
  • [ 63909-54-6 ]
  • [4-(2-fluoro-benzyl)-piperidin-1-yl]-acetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1,3-dimethyl-2-imidazolidinone; sodium hydride / 0.33 h / 20 °C 2: H2 / Pd(OH)2/C / ethanol / 15 h / 20 °C / 2585.74 Torr 3: diisopropylethylamine / dimethylformamide / 1 h / 20 °C
  • 20
  • [ 63909-54-6 ]
  • 2-[4-(2-fluoro-benzyl)-piperidin-1-ylmethyl]-3<i>H</i>-benzoimidazol-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 1,3-dimethyl-2-imidazolidinone; sodium hydride / 0.33 h / 20 °C 2.1: H2 / Pd(OH)2/C / ethanol / 15 h / 20 °C / 2585.74 Torr 3.1: diisopropylethylamine / dimethylformamide / 1 h / 20 °C 4.1: aq. HCl / 1 h / 100 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole; triethylamine / dimethylformamide / 0.33 h / 20 °C 5.2: acetic acid / 0.25 h / 140 °C 6.1: aq. HBr / 3 h / 100 °C
  • 21
  • [ 63909-54-6 ]
  • 2-[4-(2-fluoro-benzyl)-piperidin-1-ylmethyl]-6-methoxy-1<i>H</i>-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 1,3-dimethyl-2-imidazolidinone; sodium hydride / 0.33 h / 20 °C 2.1: H2 / Pd(OH)2/C / ethanol / 15 h / 20 °C / 2585.74 Torr 3.1: diisopropylethylamine / dimethylformamide / 1 h / 20 °C 4.1: aq. HCl / 1 h / 100 °C 5.1: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole; triethylamine / dimethylformamide / 0.33 h / 20 °C 5.2: acetic acid / 0.25 h / 140 °C
  • 22
  • [ 63909-54-6 ]
  • [4-(2-fluoro-benzyl)-piperidin-1-yl]-acetic acid; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1,3-dimethyl-2-imidazolidinone; sodium hydride / 0.33 h / 20 °C 2: H2 / Pd(OH)2/C / ethanol / 15 h / 20 °C / 2585.74 Torr 3: diisopropylethylamine / dimethylformamide / 1 h / 20 °C 4: aq. HCl / 1 h / 100 °C
  • 23
  • [ 63909-54-6 ]
  • diethyl α-fluoro-2-fluorobenzylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi, HMDS, 2.) NFBS / 1.) hexane, THF, -78 deg C -> 20 deg C; 20 deg C, 15 min, 2.) THF, -90 deg C, 15 min; -90 deg C -> 0 deg C 2: LiOH, H2O / 0.25 h / 0 °C
Multi-step reaction with 3 steps 1: 1.) LiHMDS / 1.) THF, -78 deg C to 0 deg C, 2.) 20 deg C 2: N-fluorobenzenesulfonimide / tetrahydrofuran / -78 - 0 °C 3: 68 percent / 1M LiOH / H2O / 0 °C
  • 24
  • [ 63909-54-6 ]
  • diethyl α-chloro-2-fluorobenzylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi, HMDS, 2.) Cl3C-CCl3 / 1.) hexane, THF, -78 deg C -> 20 deg C; 20 deg C, 15 min, 2.) THF, -78 deg C, 15 min; -78 deg C -> 0 deg C 2: EtOLi / ethanol / 0.25 h / 0 °C
Multi-step reaction with 3 steps 1: 1.) LiHMDS / 1.) THF, -78 deg C to 0 deg C, 2.) 20 deg C 2: hexachloroethane / tetrahydrofuran / -78 - 0 °C 3: 92 percent / 1M LiOH / H2O / 0 °C
  • 25
  • [ 63909-54-6 ]
  • diethyl α-bromo-2-fluorobenzylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi, HMDS, 2.) BrCl2C-CCl2Br / 1.) hexane, THF, -78 deg C -> 20 deg C; 20 deg C, 15 min, 2.) THF, -78 deg C, 15 min; -78 deg C -> 0 deg C 2: EtOLi / ethanol / 0.25 h / 0 °C
  • 26
  • [ 63909-54-6 ]
  • [ 209626-94-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) LiHMDS / 1.) THF, -78 deg C to 0 deg C, 2.) 20 deg C 2: N-fluorobenzenesulfonimide / tetrahydrofuran / -78 - 0 °C
  • 27
  • [ 63909-54-6 ]
  • [ 209627-00-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) LiHMDS / 1.) THF, -78 deg C to 0 deg C, 2.) 20 deg C 2: hexachloroethane / tetrahydrofuran / -78 - 0 °C
  • 28
  • [ 63909-54-6 ]
  • [ 338732-52-8 ]
YieldReaction ConditionsOperation in experiment
3 2-[3-(2-Fluoro-benzyl)-8-aza-bicyclo[3.2.1]oct-8-ylmethyl-]-1H-benzimidazole was prepared by following the procedures described above for Example 1, but substituting diethyl 2-fluorobenzylphosphonate for diethyl 4-chlorophosphonate. Chromatography yielded a mixture of exo and endo 2-[3-(2-fluoro-benzyl)-8-aza-bicyclo[3.2.1]oct-8-ylmethyl]-1H-benzimidazole: MS (m+1)=350; 1H NMR (400 MHz, CDCl3 10 (br, 1H), 7.6 (br, 2H), 7.5 (br, 1H), 7.2 (m, 4H), 6.9 (m, 2H), 3.9 (s, 2H), 3.25 (s, 2H), 2.8 (d, 0.6*2H, endo), 2.55 (d, 0.4*2H, exo), 2.2 (m, 4H), 1.9 (d, 2H), 1.7-1.4 (m, 3H).
  • 32
  • [ 762-04-9 ]
  • [ 90555-36-5 ]
  • [ 63909-54-6 ]
YieldReaction ConditionsOperation in experiment
51% With copper(l) iodide; caesium carbonate In 1,2-dimethoxyethane at 85℃; for 2h; Inert atmosphere; General procedure: Under an argon atmosphere, the carbonyl compounds (0.40 mmol), TsNHNH2 (0.42 mmol, 1.05 eq) and DME (1.0 mL) were successively added to a flame-dried Schlenk flask. The reaction was heated at 60 ºC with stirring for 30 minutes. After the solution cooled down to room temperature H-Phosphonate 1b (0.40 mmol, 1.0 eq), Cs2CO3 (0.60 mmol, 1.5 eq), and CuI (0.04 mmol, 10 mol %) were sequentially added to the system. The mixture was stirred to 85oC. When the reaction was considered complete, as determined by TLC analysis, the reaction mixture was cooled to room temperature and filtered through a short plug of silica gel [washed with EtOAc]. Solvent was then removed in vacuo to provide a crude mixture, which was purified by silica gel column chromatography to afford pure product.
  • 33
  • [ 446-52-6 ]
  • [ 63909-54-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 0.5 h / 20 °C 2: copper(l) iodide; caesium carbonate / 1,2-dimethoxyethane / 2 h / 85 °C / Inert atmosphere
  • 34
  • [ 63909-54-6 ]
  • [ 135-02-4 ]
  • (E)-1-fluoro-2-(2-methoxystyryl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.5h; Stage #2: ortho-anisaldehyde In tetrahydrofuran at 0 - 20℃; for 20h; 5.2.2. General procedure for synthesis of stilbenes General procedure: The appropriately substituted phosphonate ester (10 mmol) was dissolved in dry tetrahydrofuran (20 ml) and stirred at 0-5 °C. Sodium hydride (25 mmol) was added to the solution slowly and after thirty minutes the appropriate freshly distilled aldehyde(10 mmol) in tetrahydrofuran (30 ml) was added dropwise. The mixture was allowed to stir at room temperature overnight. In order to increase the yield, compounds 35, 37 and 40 were heated under reflux for 3-4 h. The mixture was cooled and quenched with ice water (10 ml) and poured onto ice. Dilute hydrochloric acid(1 M) was added until acidic and the solution was extracted with ethyl acetate (4 50 ml). The combined organic layers were washed with saturated salt and dried over magnesium sulfate. Filtration and evaporation of the ethyl acetate afforded crude stilbene products as oils or solids. The solids were crystallized from 95% ethanol to afford crystalline stilbenes. The oils were chromatographed on silica gel using methylene chloride to give pure products.(E)-1-Fluoro-2-(2-methoxystyryl)benzene 10: 98% yield, white crystals; mp 34-35 °C; 1H NMR (CDCl3, 300 MHz): d 7.66 (dt,J = 7.8, 1.6 Hz, 1H), 7.62 (dd, J = 7.6, 1.5 Hz, 1H), 7.54 (d,J = 16.6 Hz, 1H), 7.27 (d, J = 16.6 Hz, 1H), 7.22 (m, 2H), 7.13 (dt,J = 7.5, 1.3 Hz, 1H), 7.05 (dt, J = 8.0, 1.3 Hz, 1H), 6.98 (t, J = 7.4 Hz,1H), 6.91 (d, J = 8.3 Hz, 1H), 3.88 (s, 3H). 13C NMR (CDCl3,75 MHz): d 160.5 (d, J = 247.7 Hz), 157.2 (s), 129.2 (s), 128.6 (d,J = 8.4 Hz), 127.0 (d, J = 3.4 Hz), 126.7 (s), 126.5 (s), 126.0 (d,J = 12.1 Hz), 125.7 (d, J = 3.6 Hz), 124.2 (d, J = 3.1 Hz), 121.1 (d,J = 4.0 Hz), 120.9 (s), 115.5 (d, J = 22.2 Hz), 110.8 (s), 55.7 (s). 19F(CDCl3, 282 MHz): d 116.9 (s, 1F). HRMS (EI) calcd for C15H13FO[M]+: 228.0950; found, 228.0950.
  • 35
  • [ 34036-07-2 ]
  • [ 63909-54-6 ]
  • (E)-1,2-difluoro-4-(2-fluorostyryl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.5h; Stage #2: 3,4 difluorobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 20h; 5.2.2. General procedure for synthesis of stilbenes General procedure: The appropriately substituted phosphonate ester (10 mmol) was dissolved in dry tetrahydrofuran (20 ml) and stirred at 0-5 °C. Sodium hydride (25 mmol) was added to the solution slowly and after thirty minutes the appropriate freshly distilled aldehyde(10 mmol) in tetrahydrofuran (30 ml) was added dropwise. The mixture was allowed to stir at room temperature overnight. In order to increase the yield, compounds 35, 37 and 40 were heated under reflux for 3-4 h. The mixture was cooled and quenched with ice water (10 ml) and poured onto ice. Dilute hydrochloric acid(1 M) was added until acidic and the solution was extracted with ethyl acetate (4 50 ml). The combined organic layers were washed with saturated salt and dried over magnesium sulfate. Filtration and evaporation of the ethyl acetate afforded crude stilbene products as oils or solids. The solids were crystallized from 95% ethanol to afford crystalline stilbenes. The oils were chromatographed on silica gel using methylene chloride to give pure products.
  • 36
  • [ 2646-90-4 ]
  • [ 63909-54-6 ]
  • (E)-1,4-difluoro-2-(2-fluorostyryl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.5h; Stage #2: 2,5-difluorobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 20h; 5.2.2. General procedure for synthesis of stilbenes General procedure: The appropriately substituted phosphonate ester (10 mmol) was dissolved in dry tetrahydrofuran (20 ml) and stirred at 0-5 °C. Sodium hydride (25 mmol) was added to the solution slowly and after thirty minutes the appropriate freshly distilled aldehyde(10 mmol) in tetrahydrofuran (30 ml) was added dropwise. The mixture was allowed to stir at room temperature overnight. In order to increase the yield, compounds 35, 37 and 40 were heated under reflux for 3-4 h. The mixture was cooled and quenched with ice water (10 ml) and poured onto ice. Dilute hydrochloric acid(1 M) was added until acidic and the solution was extracted with ethyl acetate (4 50 ml). The combined organic layers were washed with saturated salt and dried over magnesium sulfate. Filtration and evaporation of the ethyl acetate afforded crude stilbene products as oils or solids. The solids were crystallized from 95% ethanol to afford crystalline stilbenes. The oils were chromatographed on silica gel using methylene chloride to give pure products.
  • 37
  • [ 1550-35-2 ]
  • [ 63909-54-6 ]
  • (E)-2,4-difluoro-1-(2-fluorostyryl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.5h; Stage #2: 2,4-difluorobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 20h; 5.2.2. General procedure for synthesis of stilbenes General procedure: The appropriately substituted phosphonate ester (10 mmol) was dissolved in dry tetrahydrofuran (20 ml) and stirred at 0-5 °C. Sodium hydride (25 mmol) was added to the solution slowly and after thirty minutes the appropriate freshly distilled aldehyde(10 mmol) in tetrahydrofuran (30 ml) was added dropwise. The mixture was allowed to stir at room temperature overnight. In order to increase the yield, compounds 35, 37 and 40 were heated under reflux for 3-4 h. The mixture was cooled and quenched with ice water (10 ml) and poured onto ice. Dilute hydrochloric acid(1 M) was added until acidic and the solution was extracted with ethyl acetate (4 50 ml). The combined organic layers were washed with saturated salt and dried over magnesium sulfate. Filtration and evaporation of the ethyl acetate afforded crude stilbene products as oils or solids. The solids were crystallized from 95% ethanol to afford crystalline stilbenes. The oils were chromatographed on silica gel using methylene chloride to give pure products.
  • 38
  • [ 122-52-1 ]
  • [ 63909-54-6 ]
YieldReaction ConditionsOperation in experiment
In neat (no solvent) at 130℃; for 20h; 5.2.1. General procedure for synthesis of phosphonate esters General procedure: Benzyl chloride or benzyl bromide derivatives (1 eq) were added to triethyl phosphite (1.5 eq) and heated to 130 °C for 20 h. After cooling, the resulting crude product was distilled in vacuo to remove excess triethyl phosphite and ethyl chloride or ethyl bromide. Purification by filtration through a pad of silica gel (70% ethyl acetate/30% hexanes) gave the phosphonate ester products as colorless oils.
at 135℃; for 24h;
  • 39
  • [ 63909-54-6 ]
  • tert-butyl (R)-2-(3-(2-fluorophenyl)oxiran-2-yl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
  • 40
  • [ 63909-54-6 ]
  • tert-butyl (R)-2-((1R,2R)-2-(2-fluorophenyl)-1-hydroxy-2-phenylethyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C
  • 41
  • [ 63909-54-6 ]
  • tert-butyl (R)-2-((1S,2S)-2-(2-fluorophenyl)-1-hydroxy-2-phenylethyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C
  • 42
  • [ 63909-54-6 ]
  • tert-butyl (R)-2-((1R,2R)-2-(2-fluorophenyl)-1-((methylsulfonyl)oxy)-2-phenylethyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C 4.1: pyridine / 2 h / 0 - 20 °C
  • 43
  • [ 63909-54-6 ]
  • (1R,2R)-2-(2-fluorophenyl)-2-phenyl-1-((R)-pyrrolidin-2-yl)ethyl methanesulfonate hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
  • 44
  • [ 63909-54-6 ]
  • (1R,2R)-1-((R)-1-(1-benzyl-5-(benzyloxy)-4-oxo-1,4-dihydropyridazine-3-carbonyl)pyrrolidin-2-yl)-2-(2-fluorophenyl)-2-phenylethyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C 6.2: 1 h / 20 °C
  • 45
  • [ 63909-54-6 ]
  • (1R,2R)-2-(2-fluorophenyl)-1-((R)-1-(5-hydroxy-4-oxo-1,4-dihydropyridazine-3-carbonyl)pyrrolidin-2-yl)-2-phenylethyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C 6.2: 1 h / 20 °C 7.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C / Inert atmosphere
  • 46
  • [ 63909-54-6 ]
  • (9aR,10S)-10-((R)-(2-fluorophenyl)(phenyl)methyl)-4-hydroxy-8,9,9a,10-tetrahydro-7H-pyrrolo[1',2':4,5]pyrazino[1,2-b]pyridazine-3,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 6.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C 6.2: 1 h / 20 °C 7.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C
  • 47
  • [ 63909-54-6 ]
  • tert-butyl (R)-2-((1S,2S)-2-(2-fluorophenyl)-1-((methylsulfonyl)oxy)-2-phenylethyl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C 4.1: pyridine / 2 h / 0 - 20 °C
  • 48
  • [ 63909-54-6 ]
  • (1R,7aR)-1-((S)-(2-fluorophenyl)(phenyl)methyl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C 3.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.92 h / -30 - 0 °C 4.1: pyridine / 2 h / 0 - 20 °C 5.1: pyridine / 2 h / 120 °C / Microwave irradiation
  • 49
  • [ 63909-54-6 ]
  • [ 73365-02-3 ]
  • tert-butyl (R,E)-2-(2-fluorostyryl)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Added a solution of lithium bis(trimethylsilyl)amide (1 .0 M in THF, 36.5 mL, 36.5 mmol) dropwise to a solution of diethyl 2-fluorobenzylphosphonate (9.08 g, 36.9 mmol) in THF (80 mL) at 0 C. Stirred at 0 C for 20 minutes, then added a solution of (R)-tert-butyl 2-formylpyrrolidine-1 - carboxylate (7 g, 35.1 mmol) in THF (30 mL) dropwise. Reaction mixture was stirred in ice bath for 1 h and then slowly warmed to RT over 1 h and then stirred for an additional 1 h at RT. The reaction was quenched with water and extracted with EtOAc (twice). The combined organic extracts were washed with brine, dried over Na2S04, filtered and concentrated. Silica gel column chromatography (EtOAc/heptane) provided tert-butyl (R,E)-2-(2-fluorostyryl)pyrrolidine- 1 -carboxylate (6.5 g, white solid) in 64% yield. MS m/z 236.3 (M-tBu+H).
  • 50
  • [ 63909-54-6 ]
  • ethyl hydrogen 2-fluorobenzylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-fluoro-1-diethylphosphonomethyl-benzene With pyridine; trifluoromethylsulfonic anhydride In dichloromethane for 0.166667h; Stage #2: With water In dichloromethane for 1h; Stage #3: With sodium hydroxide In diethyl ether for 0.5h;
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