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Chemical Structure| 399-25-7 Chemical Structure| 399-25-7

Structure of 399-25-7

Chemical Structure| 399-25-7

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Product Details of [ 399-25-7 ]

CAS No. :399-25-7
Formula : C8H6FNO2
M.W : 167.14
SMILES Code : O=[N+](/C=C/C1=CC=CC=C1F)[O-]
MDL No. :MFCD00042451
InChI Key :NKZSNHAEWKEFNE-AATRIKPKSA-N
Pubchem ID :5383481

Safety of [ 399-25-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 399-25-7 ]

* 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 [ 399-25-7 ]

[ 399-25-7 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 75-52-5 ]
  • [ 446-52-6 ]
  • [ 399-25-7 ]
YieldReaction ConditionsOperation in experiment
77.7% 2- fluorobenzaldehyde (7.747g, 62.46mmol), nitromethane (4mL), methanol (10 mL) to prepare a solution; in methanol (60mL), water (30mL), sodium hydroxide (2.5N, 30mL) was prepared as a solution, maintaining the temperature at 5 ; the former solution is added dropwise to the latter solution was added dropwise for about 30-60min, the solution temperature maintained at 5-10 ; after dropwise addition of the above solution was added dropwise to zinc chloride (42.6g, 31.25mmol), concentrated hydrochloric acid (13mL), water (17mL) mixed solution was added dropwise while maintaining a temperature of 0-10 deg.] C, the reaction after 2-4h dropwise at room temperature; after the reaction, reduction pressure filtration with 40% methanol solution of the filter cake was washed several times, that was the pale yellow product 8.1g, yield 77.7%.
With sodium hydroxide; In methanol; water; at -4 - -2℃; for 0.25h; General procedure: Sodium hydroxide (61 mmol) in 15 mL of ice-water was added dropwise to a solution of appropriate aromatic aldehyde (58 mmol) and nitromethane (3.20 mL, 58 mmol) in 250 mL of methanol at -2 to -4C (ice-salt bath). After being stirred at -2 to -4C for 15 min, the solution was added dropwise to 35 mL of 4N aqueous hydrochloric acid while stirring. When the addition was completed, the reaction mixture was extracted with diethyl ether, then the organic layer was washed with a small volume of brine, and dried over anhydrous sodium sulphate. The reaction was monitored by TLC using hexane:ethyl acetate (7:3) as mobile phase and iodine as the detecting agent. Finally, the organic layer was evaporated to give the respective nitrostyrene. The crude product was recrystallized by ethanol [3].
  • 2
  • [ 399-25-7 ]
  • [ 52721-69-4 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran;Reflux; General procedure: Corresponding nitrostyrene (45 mmol) in 200 mL of dry THF was added dropwise to lithium aluminum hydride (180 mmol) in 200 mL of dry THF, and the mixture was refluxed for 2-4 h. The reaction was monitored by TLC using n-butanol:ethanol (3:7) as mobile phase and iodine as a visualizing agent. Then the reaction mixture was treated with 10 mL of water, 10 mL of 15% aqueous sodium hydroxide, and 20 mL of water, filtered, dried over anhydrous sodium sulphate, and evaporated to give crude respective aromatic ethyl amines. The crude product was recrystallized using ethanol [3].
  • 3
  • [ 16940-66-2 ]
  • [ 399-25-7 ]
  • [ 829-85-6 ]
  • [ 934167-92-7 ]
  • 4
  • [ 399-25-7 ]
  • [ 123-54-6 ]
  • [ 1073917-19-7 ]
  • 5
  • [ 399-25-7 ]
  • 2-phenyl-4-isopropyl-5-oxazolone [ No CAS ]
  • [ 1132767-79-3 ]
  • 7
  • [ 36635-61-7 ]
  • [ 399-25-7 ]
  • [ 541-41-3 ]
  • [ 1173094-27-3 ]
  • [ 1173094-30-8 ]
  • 8
  • [ 685-88-1 ]
  • [ 399-25-7 ]
  • [ 1201676-71-2 ]
  • 9
  • [ 399-25-7 ]
  • [ 372-31-6 ]
  • [ 1228935-47-4 ]
  • 10
  • [ 399-25-7 ]
  • [ 504-02-9 ]
  • [ 1228387-94-7 ]
  • [ 1228387-96-9 ]
  • 11
  • [ 399-25-7 ]
  • [ 126-81-8 ]
  • [ 1228387-84-5 ]
  • [ 1228387-85-6 ]
  • 12
  • [ 917473-35-9 ]
  • [ 399-25-7 ]
  • 1-(3-{3-dimethoxymethyl-4-[1-(2-fluoro-phenyl)-2-nitro-ethyl]-phenoxy}-propyl)-piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Step C. 1-(3-{3-Dimethoxymethyl-4-[1-(2-fluoro-phenyl)-2-nitro-ethyl]-phenoxy}-propyl)-piperidine. A -78 C. solution of 5-bromo-4-dimethoxymethyl-2-(3-piperidin-1-yl-propoxy)-pyridine (359 mg, 0.962 mmol) in THF (8 mL) was treated with n-BuLi (2.5 M in hexanes; 0.4 mL). After 20 min at -78 C., the mixture was treated with a solution of <strong>[399-25-7]1-fluoro-2-(2-nitro-vinyl)-benzene</strong> (171 mg, 1.02 mmol) in THF (5 mL). After 20 min at -78 C., the mixture was treated with acetic acid (1 mL) and was allowed to warm to 0 C. The mixture was concentrated and the residue was chromatographed (SiO2; 1-10% 2 M NH3 in MeOH/DCM) to give the title compound (285 mg, 64%) as an oil. MS (ESI): mass calcd. for C24H32FN3O5, 461.23; m/z found, 462.5 [M+H]+. 1H NMR (CDCl3): 8.03 (s, 1H), 7.30-7.24 (m, 2H), 7.15-7.03 (m, 2H), 6.95 (s, 1H), 5.55 (t, 8.2, 1H), 5.43 (s, 1H), 5.02-4.92 (m, 2H), 4.34-4.27 (m 2H), 3.35 (s, 3H), 3.27 (s, 3H), 2.55-2.42 (m, 6H), 2.05-1.95 (m, 2H), 1.69-1.60 (m, 4H), 1.49-1.42 (m, 2H).
  • 13
  • [ 399-25-7 ]
  • [ 55-21-0 ]
  • 1-benzamido-2,2-dichloro-1-(2-fluorophenyl)-2-nitroethane [ No CAS ]
  • 14
  • [ 1670-46-8 ]
  • [ 399-25-7 ]
  • 2-acetyl-2-((S)-1-(2-fluorophenyl)-2-nitroethyl)cyclopentan-1-one [ No CAS ]
  • C15H16FNO4 [ No CAS ]
  • 2-acetyl-2-((S)-1-(2-fluorophenyl)-2-nitroethyl)cyclopentan-1-one [ No CAS ]
  • [ 1272317-75-5 ]
YieldReaction ConditionsOperation in experiment
With C28H30N4O3; In toluene; at 4℃; for 72h; To a stirred solution of 6a (11.4 mg, 0.0765 mmol) and (S)-5m (3.60 mg, 0.00765 mmol) in toluene (76.5 μL) at 4 C was added 2-acetylcyclopentanone (18.2 μL, 0.153 mmol), and the resulting mixture was kept stirring at the same temperature. After 24 h, the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by flash column chromatography (hexane/AcOEt = 5/1) to give 8a and 8a' (21.0 mg, 99% yield, dr = 6.5:1) as colorless oil.
  • 15
  • [ 1076-38-6 ]
  • [ 399-25-7 ]
  • [ 1296198-83-8 ]
YieldReaction ConditionsOperation in experiment
85% With water; at 30℃; for 9h;Inert atmosphere; Sonication; General procedure: A mixture of 4-hydroxycoumarin (10) (1 mmol) and β-nitrostyrene (11) (1.2 mmol) was suspended in 5 mL of water in a 20 mL vial. The vial was placed into the ultrasonic bath (Branson Ultrasonics, Ultrasonic bath Model 3010R-DTH, 50 kHz frequency) at 30 C for the specific time mentioned in Table 2. The progress of the reaction was monitored by TLC. After completion of the reaction, the resulting solid product was filtered and washed with water (2×10 mL) and n-hexane (5×10 mL). Then solid was dried under vacuum to obtain the product (12a-n) in almost pure form in exellent yields (83-94%).
  • 16
  • [ 399-25-7 ]
  • [ 104-55-2 ]
  • C17H16FNO3 [ No CAS ]
  • 17
  • [ 399-25-7 ]
  • [ 104-55-2 ]
  • [ 1296869-83-4 ]
  • 18
  • [ 399-25-7 ]
  • [ 144027-22-5 ]
  • [2-[1-(2-fluorophenyl)2-nitroethyl]-2-(phenylselanyl)-2,3-dihydro-1H-inden-1-one] [ No CAS ]
  • [ 1303532-59-3 ]
  • 19
  • [ 399-25-7 ]
  • [ 93102-05-7 ]
  • (trans)-1-benzyl-3-(2-fluoro-phenyl)-4-nitro-pyrroIidine [ No CAS ]
  • 21
  • [ 17299-34-2 ]
  • [ 399-25-7 ]
  • [ 1352139-29-7 ]
  • C16H18FNO3 [ No CAS ]
  • 22
  • [ 120-72-9 ]
  • [ 399-25-7 ]
  • (R)-3-[1-(2-fluorophenyl)-2-nitroethyl]-1H-indole [ No CAS ]
  • 23
  • [ 13176-46-0 ]
  • [ 399-25-7 ]
  • [ 1361938-48-8 ]
  • 24
  • [ 399-25-7 ]
  • [ 123-72-8 ]
  • [ 1355451-85-2 ]
  • 25
  • [ 288-13-1 ]
  • [ 399-25-7 ]
  • [ 1374822-79-3 ]
  • 26
  • [ 83-72-7 ]
  • [ 399-25-7 ]
  • (R)-2-[1-(2-fluorophenyl)-2-nitroethyl]-3-hydroxy-1,4-naphthoquinone [ No CAS ]
  • 27
  • [ 4883-67-4 ]
  • [ 399-25-7 ]
  • [ 1395408-74-8 ]
  • [ 1395408-69-1 ]
  • 28
  • [ 4883-67-4 ]
  • [ 399-25-7 ]
  • [ 1395408-69-1 ]
  • 29
  • [ 603-76-9 ]
  • [ 399-25-7 ]
  • 3-(1-(2-fluorophenyl)-2-nitroethyl)-1-methyl-1H-indole [ No CAS ]
  • 3-(1-(2-fluorophenyl)-2-nitroethyl)-1-methyl-1H-indole [ No CAS ]
  • 30
  • [ 4883-67-4 ]
  • [ 399-25-7 ]
  • 2-[1-(2-fluorophenyl)-2-nitroethyl]-2-nitrocyclohexanone [ No CAS ]
  • (RS)-2-[(SR)-1-(2-fluorophenyl)-2-nitroethyl]-2-nitrocyclohexanone [ No CAS ]
  • 31
  • [ 4883-67-4 ]
  • [ 399-25-7 ]
  • [ 1395408-74-8 ]
  • [ 1395408-69-1 ]
  • (RS)-2-[(SR)-1-(2-fluorophenyl)-2-nitroethyl]-2-nitrocyclohexanone [ No CAS ]
  • 32
  • [ 4883-67-4 ]
  • [ 399-25-7 ]
  • [ 1395408-74-8 ]
  • (RS)-2-[(SR)-1-(2-fluorophenyl)-2-nitroethyl]-2-nitrocyclohexanone [ No CAS ]
  • 33
  • [ 399-25-7 ]
  • [ 123-54-6 ]
  • [ 1427416-65-6 ]
  • 34
  • [ 83-72-7 ]
  • [ 399-25-7 ]
  • [ 1391940-87-6 ]
YieldReaction ConditionsOperation in experiment
With C22H39N3OSSi; In toluene; at 0℃; General procedure: To a cooled solution (0 oC) of β-nitroalkenes 3 (0.24 mmol) and catalyst 1d (0.006 mmol) in anhydrous toluene (4 mL) was added 2-hydroxy-1,4-naphthoquinone 2 (0.2 mmol). The reaction mixture was stirred at 0 oC for the requisite times as indicated in Table 3. Then mixture was purified by silica gel column chromatography (CH2Cl2) to afford the desired products 4.
  • 35
  • [ 1374450-07-3 ]
  • [ 399-25-7 ]
  • [ 1442688-92-7 ]
  • 36
  • [ 399-25-7 ]
  • [ 105-53-3 ]
  • [ 1448173-61-2 ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine; calcium chloride; at 20℃; for 0.5h;Milling; General procedure: A stainless-steel jar (10mL) was charged with nitrostyrene 2a (0.33mmol), diethyl malonate 1a (0.30mmol), Et3N (0.30mmol), CaCl2 (0.30mmol), and a stainless-steel ball (D=10mm) successively. Stirring was started in a grinding bowl using the ball mill (Retsch MM400 Mixer Mill, Retsch GmbH, Haan, Germany) with a vibration rate of 20Hz for 30min. The crude product was washed off the reaction vessel with CH2Cl2, and the combined organic fractions were filtered and concentrated in vacuo. Purification by flash chromatography on silica gel (EtOAc/hexanes=1:20) afforded the pure product 3a.
  • 37
  • [ 399-25-7 ]
  • [ 89-25-8 ]
  • (R)-4-[1-(2-fluorophenyl)-2-nitroethyl]-5-methyl-2-phenyl-2H-pyrazol-3-ol [ No CAS ]
  • 38
  • [ 95-20-5 ]
  • [ 399-25-7 ]
  • [ 1459775-48-4 ]
  • 39
  • [ 399-25-7 ]
  • [ 250351-17-8 ]
  • C20H26FNO6Si [ No CAS ]
  • 40
  • [ 399-25-7 ]
  • [ 78-84-2 ]
  • [ 1609238-55-2 ]
  • (S)-3-(2-fluorophenyl)-2,2-dimethyl-4-nitrobutanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C13H28N2; benzoic acid; In neat (no solvent); at 4℃; for 24h;Green chemistry; General procedure: Typical procedure for the asymmetric Michael reaction: The a,a-disubstitutedaldehyde (1.6 mmol) and nitroolefin (0.4 mmol) were added to a mixture of thediamine catalyst 1c (8.5 mg, 0.04 mmol) and benzoic acid (4.9 mg, 0.04 mmol).The reaction mixture was stirred at 4 C for the time as indicated in the Tables2 and 3. The reaction mixture was stirred until complete conversion of thenitroolefin (monitored by TLC) and then was purified by flash columnchromatography on silica gel (ethyl acetate/hexanes = 1:10) to afford thepure Michael product. The enantiomeric excess (ee) of the products 4a-j and5a-e was determined by chiral HPLC analysis.
  • 41
  • [ 399-25-7 ]
  • [ 67-64-1 ]
  • [ 1614219-51-0 ]
  • [ 1613450-85-3 ]
YieldReaction ConditionsOperation in experiment
With 1-((1R,2R)-2-aminocyclohexyl)-3-(9H-fluoren-9-yl)thiourea; p-Toluic acid; In 1,4-dioxane; at 20℃; for 24h; General procedure: To a stirred solution of trans-β-nitrostyrene 1a (Ar = Ph, 0.0745 g, 0.5 mmol)and acetone 2a (R = CH3, about 0.185 mL, 2.5 mmol) in 1,4-dioxane (0.5 mL),primary amine-thiourea IV (0.0253 g, 15 mol%) and 4-methylbenzoic acid (0.0103 g,15 mol%) were added. After being stirred for 24 h at room temperature, the reactionmixture was concentrated in vacuo. The residue was purified by columnchromatography on silica gel to afford desired Michael adduct 3aa (R = CH3, Ar = Ph,0.0890 g, 86%).
  • 42
  • 3-Amino-1-methyl-2-indolinone Monohydrochloride [ No CAS ]
  • [ 399-25-7 ]
  • [ 100-52-7 ]
  • C24H20FN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In chloroform; for 24h;Reflux; General procedure: Typical experimental procedure for 4aa: To a solution of 3-Amino-1-methylindolin-2-one hydrochloride 1a (0.1 mmol), benzaldehyde2a (0.1 mmol), nitroalkene 3a (0.1 mmol) in chloroform (0.5 mL), was added triethylamine(0.1 mmol). The reaction mixture was stirred under the reflux temperature. After completionof the reaction (TLC), the solvent was removed under vacuum. The crude product was subjected to column chromatography on silica gel using petroleum ether /ethyl acetate (3:1)as the eluent to give 4aa.Compounds 4ba-4wa were synthesized by a similar procedure as described for compound4aa. For the separation of these compounds, the eluent of silica gel column chromatographyconsisted of appropriate mixtures of petroleum ether and ethyl acetate.
  • 43
  • [ 399-25-7 ]
  • [ 123-54-6 ]
  • [ 1639342-46-3 ]
YieldReaction ConditionsOperation in experiment
92% General procedure: To a solution of nitroolefin (0.33 mmol) in CH2Cl2 (1.5 ml) was added bifunctional catalyst 1f (2mg, 0.0033 mmol, 1 mol %) and the mixture was stirred for 5 min under N2 atmosphere. Then1,3-dicarbonyl compound (0.4 mmol) was added to the mixture. Upon consumption ofnitroolefin substrate (monitored by TLC), the reaction mixture was concentrated and purified bycolumn chromatography to afford the conjugate addition products 4, 6 and 7.
  • 44
  • C8H12O3 [ No CAS ]
  • [ 399-25-7 ]
  • C16H18FNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% General procedure: To a solution of nitroolefin (0.33 mmol) in CH2Cl2 (1.5 ml) was added bifunctional catalyst 1f (2mg, 0.0033 mmol, 1 mol %) and the mixture was stirred for 5 min under N2 atmosphere. Then1,3-dicarbonyl compound (0.4 mmol) was added to the mixture. Upon consumption ofnitroolefin substrate (monitored by TLC), the reaction mixture was concentrated and purified bycolumn chromatography to afford the conjugate addition products 4, 6 and 7.
  • 45
  • [ 68235-96-1 ]
  • [ 399-25-7 ]
  • (R)-3-chloro-3-((S)-1-(2-fluorophenyl)-2-nitroethyl)indolin-2-one [ No CAS ]
  • C16H12ClFN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C49H35F6N3O2; In dichloromethane; at 20℃; for 24h; General procedure: To a solutionof 3-chloroxindole (1a, 0.3 mmol, 50.3 mg) and catalyst VIII(0.015 mmol, 12.2 mg) in CH2Cl2 (3.0 mL) was added β-nitrostyrene (2a, 0.45 mmol, 67.1 mg). Reaction mixture was stirred for 1 day at room temperature, concentrated, andpurified by flash column chromatography (CH2Cl2:EtOAc= 20:1) to afford the Michael adduct (3a, 83 mg, 83%).
  • 46
  • [ 399-25-7 ]
  • diethyl (1-fluoro-2-oxo-2-phenylethyl)phosphonate [ No CAS ]
  • diethyl ((2R,3S)-2-fluoro-3-(2-fluorophenyl)-4-nitro-1-oxo-1-phenylbutan-2-yl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With Ni(II) bis[N,N’-dibenzylcyclohexane-1,2-diamine]dibromide; In toluene; at 50℃; for 12h; General procedure: To a stirred solution of diethyl (1-fluoro-2-oxo-2-phenylethyl)phosphonate (1a, 82.2 mg, 0.3 mmol) and catalyst 4c (2.6 mg, 3 μmol) in toluene (1.2 mL) was added β-nitrostyrene (2a, 44.7 mg, 0.3 mmol) at room temperature. The reaction mixture was stirred for 7 h at 50 C. After completion of the reaction, the resulting solution was concentrated in vacuo and the obtained residue was purified by flash column chromatography (EtOAc:Hex, 1:3) to afford diethyl ((2R, 3S)-2-fluoro-4-nitro-1-oxo-1,3-diphenylbutan-2-yl)phosphonate (3a, 90% yield, 114 mg). Diethyl ((2R, 3S)-2-fluoro-4-nitro-1-oxo-1,3-diphenylbutan-2-yl)phosphonate (3a): [α]27D = -25.2 (c = 1.0, CHCl3); 1H NMR (400 MHz, CDCl3) δ 1.12-1.16 (t, J = 14.0 Hz, 3H), 1.25-1.28(t, J = 13.6 Hz, 3H), 3.93-4.09 (m, 4H), 4.58-4.68 (m, 1H), 4.99-5.07 (m, 2H), 7.29-7.41 (m, 7H), 7.53-7.57 (t, J = 15.2 Hz, 1H), 7.78-7.80 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 16.08 (d, J = 5.7 Hz), 16.36 (d, J = 5.7 Hz), (d, J = 21.0 Hz), 64.42 (d, J = 6.7 Hz), 64.80 (d, J = 6.7 Hz), 75.59 (t, J = 6.7 Hz), 102.73 (dd, J = 157.4 Hz, 206.0 Hz), 128.30, 128.64, 128.78, 129.81 (d, J = 8.5 Hz), 129.93, 133.15 (d, J = 6.7 Hz), 133.73, 135.46, 197.68 (dd, J = 1.8 Hz, 22.9 Hz); 31P NMR (162 MHz, CDCl3) δ 10.99 (d, J = 78.6 Hz); 19F NMR (376 MHz, CDCl3) δ -174.80 (dd, J = 23.3 Hz, 80.8 Hz); ESI-HRMS: m/z calcd for C20H24FNO6P [M+H]+: 424.1325; found 424.1331; the ee value was 99%, tR(major) = 45.10 min, tR(minor) = 50.25 min (Chiralpak IA-3, λ = 220 nm, 3% i-PrOH/hexanes, flow rate = 1 mL/min).
  • 47
  • [ 399-25-7 ]
  • [ 4105-21-9 ]
  • 3-(1-(2-fluorophenyl)-2-nitroethyl)-2-phenylimidazo[1,2-a]pyridine [ No CAS ]
  • 48
  • [ 399-25-7 ]
  • [ 61832-41-5 ]
  • 4-(2-fluorophenyl)-1-methyl-2-(methylthio)-3-nitro-1H-pyrrole [ No CAS ]
  • 49
  • [ 399-25-7 ]
  • [ 126079-16-1 ]
  • (2S,3R)-methyl 2-amino-3-(2-fluorophenyl)-4-nitrobutanoate [ No CAS ]
  • 50
  • [ 399-25-7 ]
  • [ 81167-39-7 ]
  • (2S,3S)-methyl 2-amino-3-(2-fluorophenyl)-4-nitrobutanoate [ No CAS ]
  • 51
  • [ 399-25-7 ]
  • diethyl (1-fluoro-2-oxo-2-phenylethyl)phosphonate [ No CAS ]
  • diethyl ((2R,3S)-2-fluoro-3-(2-fluorophenyl)-4-nitro-1-oxo-1-phenylbutan-2-yl)phosphonate [ No CAS ]
  • C20H22F2NO6P [ No CAS ]
  • C20H22F2NO6P [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C41H33F6N3O2; In toluene; at 20℃; for 120h; General procedure: To a stirred solution of diethyl (1-fluoro-2-oxo-2-phenylethyl)phosphonate (1,82.2 mg, 0.3 mmol) and catalyst IV (21.4 mg, 0.03 mmol) in toluene (1.2 mL) was added β-nitrostyrene (2a, 44.7 mg, 0.3 mmol) at room temperature. The reaction mixture was stirred for 3 days at room temperature. After completion of the reaction, the resulting solution was concentrated in vacuo and the obtained residue was purified by flash column chromatography (EtOAc:hexane, 1:3) to afford diethyl ((2R, 3S)-2-fluoro-4-nitro-1-oxo-1,3-diphenylbutan-2-yl)phosphonate (3a, 86% yield, 109 mg).
  • 52
  • [ 399-25-7 ]
  • [ 108-26-9 ]
  • C12H12FN3O3 [ No CAS ]
  • C12H12FN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C33H30F6N4O3; In dichloromethane; at 20℃; for 24h;Inert atmosphere; General procedure: To a solution of nitroolefin 3 (0.33 mmol) in CH2Cl2 (1.5 ml) was added bifunctional catalyst 1i (2 mg,0.0033 mmol, 1 mol %) and the mixture was stirred for 5 min under N2 atmosphere. Then pyrazolin-5-one 2 (0.4 mmol) was added to the mixture. Upon consumption of nitroolefin substrate (monitored by TLC), the reaction mixture was concentrated and purified by silica gel column chromatography to afford the conjugate addition products 4.
  • 53
  • [ 924-44-7 ]
  • [ 399-25-7 ]
  • [ 108-98-5 ]
  • (2S,3S,4S)-ethyl 4-(2-fluorophenyl)-2-hydroxy-3-nitro-4-(phenylthio)butanoate [ No CAS ]
  • 54
  • [ 504-29-0 ]
  • [ 399-25-7 ]
  • 2-(2-fluorophenyl)-3-nitroimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With pyridine; tert.-butylhydroperoxide; iodine; In acetonitrile; at 20℃; for 12h;Green chemistry; General procedure: In a 50-mL round-bottomed flask, a mixture of2-aminopyridine (1 mmol) and nitroolefin (1.05 mmol)was stirred in 10 mL acetonitrile. Then, I2 (0.2 mmol),TBHP (2 mmol), and pyridine (0.05 mL) were added to theabove mixture, and the resulting mixture was allowed tostir under reflux or at room temperature for the specifiedtime (Table 2). The progress of the reaction was monitoredby thin-layer chromatography (TLC). After the completionof the reaction, the reaction mixture was cooled to roomtemperature and poured into saturated sodium bisulfite solution (15 mL). After sonication for 10 min, the mixturewas extracted with ethyl acetate (3 × 15 mL), followed bydrying with anhydrous MgSO4. After evaporation of thesolvent, the residue was purified by flash chromatographyto afford the desired product.
 

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Aryls

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Alkenyls

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Nitroes

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