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[ CAS No. 1608-51-1 ] {[proInfo.proName]}

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Chemical Structure| 1608-51-1
Chemical Structure| 1608-51-1
Structure of 1608-51-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1608-51-1 ]

CAS No. :1608-51-1 MDL No. :MFCD00443467
Formula : C15H11FO Boiling Point : -
Linear Structure Formula :- InChI Key :NYSCQZARWVHQBE-DHZHZOJOSA-N
M.W : 226.25 Pubchem ID :5366988
Synonyms :

Calculated chemistry of [ 1608-51-1 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 66.21
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.64
Log Po/w (XLOGP3) : 3.18
Log Po/w (WLOGP) : 4.03
Log Po/w (MLOGP) : 3.83
Log Po/w (SILICOS-IT) : 4.35
Consensus Log Po/w : 3.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.57
Solubility : 0.0608 mg/ml ; 0.000269 mol/l
Class : Soluble
Log S (Ali) : -3.21
Solubility : 0.14 mg/ml ; 0.000617 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.24
Solubility : 0.0013 mg/ml ; 0.00000577 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.4

Safety of [ 1608-51-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1608-51-1 ]

* 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 [ 1608-51-1 ]

[ 1608-51-1 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 1608-51-1 ]
  • [ 6277-78-7 ]
  • [ 98991-34-5 ]
YieldReaction ConditionsOperation in experiment
62% With ammonium acetate In acetic acid 1.) reflux, 6 h, 2.) room temp., overnight;
  • 2
  • [ 25357-56-6 ]
  • [ 1608-51-1 ]
  • 2-(4-Chloro-phenyl)-4-(4-fluoro-phenyl)-6-phenyl-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With ammonium acetate In acetic acid 120 deg C, 6-8 h, RT;
  • 3
  • [ 1608-51-1 ]
  • trans-2,3-epoxy-3-(4-fluorophenyl)-1-phenylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With lithium hydroxide; dihydrogen peroxide In diethyl ether at 20℃; for 28h;
84% With dihydrogen peroxide; sodium hydroxide In methanol; water for 2h; Preparation of epoxichalcones (6a-i): Chalcone (5a-i) (0.5mmol) was solubilized in methanol (5.00mL) and an aqueous solution of sodium hydroxide 25% w/v (1.00mL, 0.6mmol) and added hydrogen peroxide 30% w/v (0.35mL, 15.0mmol). The reaction mixture was remained under stirring during 2h and monitored by TLC (ethyl acetate:hexane 7:3 v/v as eluent; UV lamp was used to visualize the plates). The solution was vacuum filtered, then was isolated epoxichalcone crystals. The solids formed were vacuum filtered and purified by recrystallization in ethanol, furnishing the respective epoxichalcone as crystals.
With 3,3-dimethyldioxirane In acetone at 30℃;
With dihydrogen peroxide; potassium carbonate In ethanol at 20℃; for 3h;
With tert.-butylhydroperoxide; tetrabutylammomium bromide; potassium hydroxide In dichloromethane; water

  • 4
  • [ 459-57-4 ]
  • [ 98-86-2 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydroxide at 20℃; for 1h;
97% With sodium para-toluenesulfonate In water at 20℃; for 2h;
96% With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Inert atmosphere; General Procedure A: Aldol condensations of ketones, esters, and amides. General procedure: To an oven-dried round-bottomed flask under N2 atmosphere was added sequentially CH2Cl2 (1 mL), aldehyde (1.2 mmol), ketone (1.0 mmol), and iPr2NEt (174 μL, 129 mg, 1.0 mmol). To the stirring solution was added dropwise trimethylsilyl trifluoromethanesulfonate (362 μL, 445 mg, 2.0 mmol) and the reaction was stirred 1 h. The reaction mixture was filtered through a plug of silica (1 cm x 5 cm) and eluted with Et2O (50 mL). The solvent was removed in vacuo and the residue was purified by column chromatography (2-5% EtOAc/hexanes).
94% Stage #1: acetophenone With sodium hydroxide In ethanol; water at 20℃; for 0.166667h; Stage #2: 4-fluorobenzaldehyde In ethanol; water at 20℃; 1.1 General procedurefor the preparation of chalcone derivatives General procedure: The substituted aryl methyl ketone (1.0 mmol), an aqueous solution of 10% sodium hydroxide (2.5 mmol) and ethanol (5 mL) were charged into a 50 mL flask, and the mixture was stirred at room temperature for 10 min, followed by addition of substitutedaryl aldehyde (1.05mmol). The reaction mixture was then stirred at room temperature and monitored using TLC with 5% ethyl acetate/petroleum ether as the solvent system until all reactants disappeared. The mixture was extracted with ethyl acetate three times, and the combined organic phase was dried over sodium sulfate and concentrated undervacuum. The residue was recrystallized from anhydrous ethanol. (E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one was obtained as a slightyellow solid in 94%. 1H NMR (600 MHz, CDCl3) δ 7.13 -7.08 (m, 2H, ArH), 7.45 (d, J = 15.7 Hz, 1H, CH=CH), 7.50 (td, J = 7.6, 1.3 Hz, 2H, ArH), 7.60 -7.56(m, 1H, ArH), 7.65 -7.61 (m, 2H, ArH), 7.77 (d, J = 15.7 Hz, 1H, CH=CH), 8.00 (dt, J = 8.3, 1.3 Hz, 2H, ArH).
94% With sodium hydroxide In ethanol; water for 1h; Cooling with ice; Preparation of chalcones (5a-i): Acetophenone (0.06mL, 5.0mmol) was solubilized in ethanol (10.0mL) and cooled in an ice bath for 15min and was added a solution of sodium hydroxide (200.0mg, 5.0mmol) in water (10.0mL). Then benzaldehyde (5.0mmol) was added. The reaction mixture was remained under stirring during 1h and monitored by TLC (thin layer chromatography) (ethyl acetate:hexane 3:7 v/v as eluent; UV lamp was used to visualize the plates). The solids formed were vacuum filtered and purified by recrystallization in ethanol, furnishing the respective chalcone as crystals.
93% With chloro-trimethyl-silane In N,N-dimethyl-formamide at 75℃; for 5h;
91% In neat (no solvent) at 130℃; for 0.583333h;
91% With sodium hydroxide In ethanol at 65℃; Flow reactor; Typical procedure for monitoring the Claisen-Schmidt reaction General procedure: Into a 50 mL volumetric flask was added 4-fluorobenzaldehyde (1.551 g, 12.5 mmol, 1 equiv) and acetophenone (1.637 g, 12.5mmol, 1 equiv). Ethanol was added to bring the total volume to 50 mL (0.25 M) and the reagents were thoroughly mixed. An aliquot of this solution (10 mL) was transferred to a 20 mL vial equipped with a Teflon-coated stir bar. The flow reactor was readied using the equipment manufacturer’s suggested start-up sequence. Ethanol was pumped at 0.5 mL/min to fill the reactor coil. The back-pressure regulator was adjusted to 7 bar and the reactor coil heated to 65 °C. After the heating coil, the product stream was intercepted with a stream of acetone (0.5 mL/min) by means of a T-piece to ensure complete solubility of the product. The Raman spectrometer was configured as in the case of monitoring formation of 1. When the flow unit was ready, 2 M NaOH (0.125 mL, 0.25 mmol) was injected all at once and after mixing for 15 s the reaction mixture was loaded into the reactor coil at a flow rate of 0.5 mL/min. After the reaction mixture had been completely loaded into the reactor, ethanol was again pumped through the coil at 0.5 mL/min. After the product had been fully discharged from the flow cell, the scans were halted. The yellow product solution was poured into a beaker containing ice (100 g) causing an immediate precipitation of the product. To ensure complete precipitation, the solution was stirred at 0 °C. The solid product was collected via vacuum filtration and washed with cold ethanol. The material was dried in air to yield (E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one, (3d, 0.5421 g, 91%) as a pale yellow solid. 1H NMR (CDCl3, 400 MHz) δ ppm 7.11 (t, J = 8.68 Hz, 2H), 7.46 (d, J = 15.89 Hz, 1H), 7.49-7.55 (m, 2H), 7.56-7.69 (m, 3H), 7.78 (d, J =15.65 Hz, 1H), 8.02 (d, J = 7.34 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ ppm 116.42 (d, J C-C-F = 22.01 Hz, CH), 122.09 (d, J C-C-C-C-F = 2.20 Hz, C), 128.76 (s, 10C), 128.94 (s, 9C), 130.62 (d, J C-C-C-F = 8.80 Hz, CH), 131.45 (d, J C-C-C-C-C-F =3.67 Hz, CH), 133.12 (C), 138.43 (C), 143.78 (CH), 164.35 (d,J C-F = 250.89 Hz, C), 190.59 (C); 19F NMR (CDCl3, 377 MHz) δ ppm -113.59, -111.32 (m) [55,56].
90% With sodium hydroxide In glycerol at 20℃; Green chemistry; General procedure for chalcones 3a-n General procedure: A solution of 5 mmol of acetophenone or 2-acetylthiophene 1, 5 mmol of aldehyde 2 and 6 mmol of sodium hydroxide (NaOH) in 5 mL of glycerin was stirred overnight, neutralized with 0.5% HCl and filtered. The solid residue was recrystallized from ethanol to obtain the purity product.
90% With iodine; triphenylphosphine In 1,4-dioxane for 12h; Reflux; General procedure for the synthesis of compounds 3 General procedure: A mixture of PPh3 (524 mg, 2.0 mmol, 1.0 equiv), I2 (507 mg, 2.0 mmol, 1.0 equiv) and 1,4-dioxane (4 mL) was stirred at rt for 30 min. Then, compounds 1 (2.0 mmol) and 2 (2.4 mmol) were added to the mixture, and stirred for appropriate time (Tabel 2) under reflux temperuture. After completion of the reaction (TLC), DCM (20 mL) was added and the solution was washed with NaS2O3 (20 mL, 10%). Then, organic layer was washed with water (2 × 20 mL) and brine (2 × 20 mL) and was dried over anhyd. MgSO4. The organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography to afford the corresponding product 3.
89% With potassium hydroxide In methanol at 25℃; for 2h;
87% at 0 - 5℃;
83% With sodium ethanolate In ethanol at 20℃; Typical method for the synthesis of Chalcones SSE14101- SSE14109 and SSE14115 General procedure: In a typical experiment, aldehyde (1 mmol) was added to Ethanol (10 mL) in a round bottom flask (25 mL). Then acetophenone (1 mmol) was added to the reaction mixture followed by addition of 15 N ethanolic solution of sodium ethoxide (0.2 mL). The reaction mixture was stirred overnight (15-17 hours) at room temperature. Then the solvent was removed and the mixture was dissolved in ethyl acetate. The contents of the flask were then transferred to the separating funnel and washed with brine. Then the organic layer was dried over MgSO4 and the solvent was removed to obtain the product. In case the product was oil, it was purified by column chromatography in EtOAc:hexane and in case of the solid, it was purified by recrystallization from ethanol.
75% With potassium hydroxide In ethanol at 20℃; for 4h;
72% With potassium hydroxide In ethanol
63% With sodium hydroxide In ethanol at 0 - 20℃; for 6h; (E)-3-(4-Fluorophenyl)-1-phenylprop-2-en-1-one (1e) To a solution of acetophenone (1.204 g, 10.0mmol) and 4-fluorobenzaldehyde (1.246 g, 10.0mmol) in MeOH (24 mL)was dropwise added 1M NaOH (10 mL) at 0 °C under open airconditions. The mixture was stirred for 6 h at room temperatureto form a precipitate. The precipitate was collected with filterpaper, and was recrystallized from MeOH to give 1e (1.435 g,6.34mmol, 63%) as yellow solid: mp = 83 °C [lit.:34 88-90°C]; 1H NMR (400 MHz, CDCl3) δ 7.12 (t, J = 8.7 Hz, 2H),7.47 (d, J = 15.8 Hz, 1H), 7.51 (t, J = 7.2 Hz, 2H), 7.60 (t,J = 7.4 Hz, 1H), 7.64 (diffused d, J = 8.7 Hz, 2H), 7.78 (d,J = 15.7 Hz, 1H), 8.02 (diffused d, J = 7.0 Hz, 2H).34
62% With sodium hydroxide In water at 20℃; Inert atmosphere; Schlenk technique;
42% With potassium hydroxide In methanol at 28℃; for 4h;
34% With potassium hydroxide In ethanol; water at 20℃; (2E)-1,3-Diphenylprop-2-en-1-one (15) General procedure: A solution of acetophenone (0.50 g, 4.16 mmol) and benzaldehyde (0.44 g, 4.16 mmol) in EtOH (5 mL) was mechanically stirred at room temperature for approximately 5 min before the dropwise addition of KOH (10% (w/v) aqueous solution, 5 mL). The subsequent reaction mixture was mechanically stirred at room temperature and continuously monitored by TLC. Upon completion, the reaction mixture was quenched with crushed ice (15 g) and acidified to pH 2 with HCl (32 wt. % in H2O, FCC). The subsequent precipitate was collected by vacuum filtration, dried (30 °C) and recrystallized from EtOH to yield the title compound 15 as light yellow crystals (0.43 g, 49%).
32% With sodium hydroxide In ethanol; water at 50℃; for 1h; Inert atmosphere; General procedure for the synthesis of para substituted (E)-chalcones from the corresponding benzaldehydes and acetophenones through an Aldol Condensation General procedure: To a solution of NaOH (2.5 g) in H20 (20 mL) that was continuously stirred was added a mixture of ketone (1 equiv, 14.2 mmol) and aldehyde (1 equiv, 14.2 mmol) in ethanol (10 mL). The mixture was heated to 50 °C and stirred for 1 hour. The solution was then cooled to room temperature, and the crude was collected via vacuum filtration. The crude product was washed with cold water and then recrystallized from ethanol or acetone, collected via vacuum filtration, and then dried under high vacuum
18% With sodium hydroxide In ethanol at 0 - 20℃; for 1h; Inert atmosphere;
With sodium ethanolate In ethanol for 16h; Ambient temperature;
With barium dihydroxide In ethanol at 30℃;
With sodium hydroxide In ethanol; water 11.a (a) (a) trans-3-(4-Fluorophenyl)-1-phenylpropenone A solution of 3.8 g (0.095 mol) of sodium hydroxide in 38 ml of water was dropped gradually into the solution of acetophenone (9.0 g, 0.075 mol) and 4-fluorobenz-aldehyde (9.4 g, 0.076 mol) in ethanol (20 ml). The mixture was stirred for 2 hr at room temperature. Water (80 ml) was added and the mixture was neutralized with 6 M HCl solution. The precipitated trans-3-(4-fluorophenyl)-1-phenylpropenone was filtered, washed with water and dried. 1H NMR (DMSO-d6): δ 7.31 (2H, t, 3J=8.9 Hz), 7.59 (2H, t, 3J=7.5 Hz), 7.68 (1H, t, 3J=7.3 Hz), 7.76 (1H, d, 3Jtrans=15.7 Hz), 7.92 (1H, d, 3Jtrans=15.5 Hz), 7.99 (2H, m), 8.16 (2H, m)
With sodium hydroxide In ethanol; water 4.A Step A: Step A: 3-(4-fluorophenyl)-1-phenyl-2-propen-1-one To a mechanically stirred solution of 5.0 g NaOH in 35 ml H2 O and 25 ml EtOH at 15° C. was added 12.0 g (0.100 mole) of acetophenone and 12.4 g (0.100 mole) of 4-fluorobenzaldehyde. After a brief exotherm to 25° C., the temperature returned to 15° C., and the cooling bath was removed. The reaction mixture was stirred at room temperature for 1.5 hour, and the thick slurry was transferred to a beaker to cool overnight at 10° C. This mixture was filtered, and the solids were washed with distilled H2 O until the washings were neutral to litmus. Upon drying in vacuo, 20.8 g of a pale yellow solid was obtained, m.p. 86°-87° C. IR (Nujol): 1660, 1605, 1590, 1580 cm-1. 1 H NMR (200 MHz, CDCl3): δ 7.12 (d, J=16 Hz, 1H), 7.42-7.68 (m, 7H), 7.78 (d, J=16 Hz, 1H), 8.02 (m, 2H).
66.25 g. (68%) With sodium hydroxide In ethanol; water 3.1 Step 1 Step 1 (Reaction CD) (E)-3-(4'-Fluorophenyl)-1-phenylprop-2-en-1-one (Compound CXXIII) 52.0 g. (433 mmoles) of acetophenone is added to a solution of 21.8 g. (545 mmoles) of sodium hydroxide in a mixture of 196 ml. of water and 122.5 ml. of 95% ethanol stirred at 20°-25° C., the resulting suspension is cooled to 0°-5° C., and 53.74 g. (433 mmoles) of 4-fluorobenzaldehyde is added portionwise, the temperature of the reaction mixture rising to 20° C. during the addition. The solidified reaction mixture is kept at 20°-25° C. for 3 hours and refrigerated for 16 hours. The solid is collected by filtration, rinsed with about 2 l. of water until the rinses are neutral, rinsed with 200 ml. of cold 95% ethanol and recrystallized from 95% ethanol to obtain the product as yellow flakes (66.25 g. (68%)), m.p. 83°-86° C.
With sodium hydroxide In ethanol; water 11.a (a) (a) trans-3-(4-Fluorophenyl)-1-phenylpropenone A solution of 3.8 g (0.095 mol) of sodium hydroxide in 38 ml of water was dropped gradually into the solution of acetophenone (9.0 g, 0.075 mol) and 4-fluorobenz-aldehyde (9.4 g, 0.076 mol) in ethanol (20 ml). The mixture was stirred for 2 hr at room temperature. Water (80 ml) was added and the mixture was neutralized with 6 M HCl solution. The precipitated trans-3-(4-fluorophenyl)-1-phenylpropenone was filtered, washed with water and dried. 1H NMR (DMSO-d6): δ 7.31 (2H, t, 3J = 8.9 Hz), 7.59 (2H, t, 3J = 7.5 Hz), 7.68 (1H, t, 3J = 7.3 Hz), 7.76 (1H, d, 3Jtrans = 15.7 Hz), 7.92 (1H, d,3Jtrans =15.5 Hz), 7.99 (2H, m), 8.16 (2H, m)
Stage #1: acetophenone With lithium hydroxide In ethanol at 25 - 30℃; for 0.583333h; Stage #2: 4-fluorobenzaldehyde In ethanol Further stages.;
With sodium hydroxide at 20℃; for 1h;
Stage #1: 4-fluorobenzaldehyde; acetophenone In ethanol for 0.5h; Reflux; Stage #2: With sodium hydroxide In ethanol General method of synthesis of (E)-Chalcones (A) General procedure: Substituted acetophenone (10 mmol) and substituted benzaldehyde (10 mmol) in ethanol (25 mL) were refluxed gently for 30 min. Then 40% NaOH (5 mL) was added and the solid was filtered, washed with water and dried to obtain shiny solid A.
With sodium hydroxide
With potassium hydroxide In methanol; water at 25℃; Inert atmosphere;
With sodium hydroxide In ethanol at 20℃; for 24h;
With sodium hydroxide In ethanol; water Synthesis and crystal growth The 4-Fluoro Chalcone compound was synthesised from a mixture of equimolar quantities of 4-fluorobenzaldehyde and acetophenone. All the reactants were of Analytical grade. The reactants were taken and stirred in ethanol (50 ml) and to this mixture solution, aqueous NaOH (3%) was added drop by drop. After a particular drop, the whole solution turned out to be a precipitate.The precipitate was dried and then recrystallized from ethanol solution. Solubility of the compound was performed with various solvents such as ethanol, acetone, chloroform, methanol and etc. Finally, we found that N,N-Dimethylformamide (DMF) can be best used as an solvent for the growth of 4FC crystals by slow evaporation solution growth method at room temperature.
With sodium hydroxide In methanol; water at 20℃; for 2h;
With sodium hydroxide In methanol; water at 0 - 20℃;
With sodium hydroxide In ethanol at 0℃; for 2h; General Procedure for Preparation of Chalcones. General procedure: A mixture of acetophenone (1 mmol, 0.12 g), sodium hydroxide(5 mL, 3N), and ethanol (30 mL, 96%) was stirred at 0C. 4-Chlorobenzaldehyde (1 mmol, 0.14 g) was added dropwise to thereaction mixture. After 2 h the product was isolated to obtain a yellow oil, which was re-crystallized from absolute ethanol toafford the pure chalcone. The other derivatives of benzaldehyde were used to prepare various chalcones.
With sodium hydroxide In ethanol; water at 20℃;
Stage #1: acetophenone With sodium hydroxide In ethanol; water at 0 - 20℃; for 1.33333h; Stage #2: 4-fluorobenzaldehyde In ethanol; water at 20℃;
With sodium hydroxide In ethanol; water at 20℃; for 3h; Inert atmosphere; 4.4. General procedure for (1) General procedure: NaOH (0.3 mol) was dissolved in water (98 mL) in ice bath before the aqueous solution was mixed with ethanol (50 mL). 5 (0.2 mol) and 6 (0.2 mol) were added to the mixture under vigorous stirring and then stirred at room temperature for 3 h. After the reaction was stopped, the resultant mixture was cooled in the refrigerator overnight and yellow precipitation was got and filtered. The residue was washed until the pH of the filtrate got to 7. The crude product was recrystallized with ethanol to yield light yellow unsaturated ketone.
Stage #1: 4-fluorobenzaldehyde With potassium hydroxide In ethanol; water at 23℃; for 0.116667h; Stage #2: acetophenone In diethyl ether; ethanol; water at 20℃; for 0.833333h;
With potassium hydroxide In ethanol; water at 4.84℃; for 24h; General procedure: Chalcone (CH) and its fluorinated derivatives (CH3F, CH4F and CH2356F) were synthesized by aldol condensation reaction in basic medium [23]: in a 50mL round bottom flask, an aqueous solution of KOH (10%, 2.60×10-3gL-1) was added to a solution of ethanol-water (6:4, v/v, 10mL). Benzaldehyde, or one of the fluorinated benzaldehydes (5.20mmol), and acetophenone (279mg, 2.33mmol) were added in small portions. The reaction mixture was stirred at low temperature (278K) for 24h. A yellow solid was formed for chalcone and a slightly yellow solid for the fluorinated chalcones. The final mixture was neutralized with hydrochloric acid (10%). The product was recrystallized three times from ethanol. Spectroscopic and spectrometric properties for all synthesized fluorinated chalcones are in full accord with the proposed structures [24,25]. Recently, the synthesis and characterization of the samples CH23F, CH25F and CH35F was already described by our group [22] (Fig. 1 ).
With alkali hydroxide In ethanol for 5h; General procedure for chalcone synthesis 3(a-p) General procedure: A mixture of acetophenone (6 mmol) and arylaldehyde (6 mmol) were dissolved in ethanol (30 mL), then 40 % solution of NaOH (6 mL) was added drop-wise, while the temperature was kept below 10 °C. The reaction mixture was stirred under this condition for 1 h. The stirring was continued at room temperature for 4 h. Thereafter the reaction mixture was poured into ice water. The precipitated solid was filtered off and recrystallized from aqueous ethanol.
With sodium hydroxide In ethanol; water at 0℃; for 0.5h;
With sodium hydroxide In ethanol
With sodium hydroxide In ethanol Cooling with ice;
With potassium hydroxide In methanol; water at 0℃;
With potassium hydroxide In ethanol; water at 0 - 20℃; for 4h; The synthesis of chalcones derivetives.[2] General procedure: Aromatic aldehydes (10 mmol, 1.0 equiv) and aromatic ketones (10 mmol, 1.0 equiv) were dissolved in 15 mL of ethanol at 0 °C. The solution was stirred for about 15 minutes. A 10 mL aliquot of a 40 % aqueous potassium hydroxide solution was then slowly added dropwise to the reaction flask. After the addition is complete, the reaction solution was allowed to stir at room temperature for approximately 4 h. Filtration yielded a solid precipitate, which was then recrystallized from ethanol.
With potassium hydroxide In ethanol
With sodium hydroxide In ethanol; water at 20℃; Inert atmosphere;

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[15]Teng, I-Jou; Tsai, Min-Chien; Shih, Shao-Fu; Tsuei, Bi-Feng; Chang, Hsin; Chuang, Yi-Ping; Lin, Chin-Sheng; Chern, Ching-Yuh; Chen, Sy-Jou [Molecules, 2018, vol. 23, # 7]
[16]Matsumoto, Shoji; Marumoto, Hayato; Akazome, Motohiro; Otani, Yasuhiko; Kaiho, Tatsuo [Bulletin of the Chemical Society of Japan, 2021, vol. 94, # 2, p. 590 - 599]
[17]Farid, Umar; Malmedy, Florence; Claveau, Romain; Albers, Lena; Wirth, Thomas [Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 7018 - 7022][Angew. Chem., 2013, vol. 125, # 27, p. 7156 - 7160,4]
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[19]Janse van Rensburg, Helena D.; Legoabe, Lesetja J.; Terre’Blanche, Gisella [Chemical Papers, 2021, vol. 75, # 4, p. 1581 - 1605]
[20]Brooks, Bailey; Hiller, Noemi; May, Jeremy A. [Tetrahedron Letters, 2021, vol. 83]
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[26]Current Patent Assignee: PURDUE UNIVERSITY SYSTEM - US5182303, 1993, A
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[28]Current Patent Assignee: ORION OYJ - EP1261588, 2004, B1
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  • 5
  • [ 1608-51-1 ]
  • [ 7152-15-0 ]
  • [ 122252-56-6 ]
YieldReaction ConditionsOperation in experiment
95% With sodium ethanolate In ethanol 1.B B. To a mixture of (E)-3-(4-fluorophenyl)-1-phenyl-2-propen-1-one (4.59 gm, 20.3 mmol) and ethyl isobutyrylacetate (3.86 gm, 24.4 mmol) in absolute EtOH (100 ml) was added a solution of EtONa in EtOH. The EtONa solution was prepared by dissolving Na metal (50 mg, 2.2 mmol) in EtOH (10 ml). After stirring at room temperature for 3 hours, additional ethyl isobutyrylacetate (1.0 gm, 6.3 mmol) was added. Stirring continued for an additional 2 hours. The mixture was poured into a separatory funnel containing Et2 O and saturated NH4 Cl. The phases were shaken and separated. The aqueous layer was extracted once with EtOAc and the combined organic layers were washed with brine and dried (Na2 SO4). Filtration and removal of the solvent gave a solid/liquid mixture. Crystallization of the residue from hot hexane/EtOAc gave β-(4-fluorophenyl)-α-(2-methyl-1-oxopropyl)-δ-oxobenzenepentanoic acid, ethyl ester (5.91 gm, ~95% one diastereomer) as colorless needles. The mother liquor was stripped and recrystallized from hot hexane to afford additional product, giving a total of 7.21 gm (92%) β-(4-fluorophenyl)-α-(2-methyl-1-oxopropyl)-δ-oxobenzenepentanoic acid, ethyl ester as a 7:3:1 mixture of diastereomers.
With sodium ethanolate In ethanol for 4.5h; Ambient temperature;
  • 6
  • [ 1608-51-1 ]
  • [ 15971-92-3 ]
  • [ 122252-66-8 ]
  • 7
  • [ 96-45-7 ]
  • [ 1608-51-1 ]
  • 7-(4-Fluoro-phenyl)-5-phenyl-2,3-dihydro-7H-imidazo[2,1-b][1,3]thiazine; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With hydrogenchloride; boron trifluoride diethyl etherate In ethanol; chloroform 1.) 0 deg C, 2 h; r.t., 14 d; 2.) 0 deg C;
  • 8
  • [ 1608-51-1 ]
  • (E)-1-phenyl-3-(4-fluorophenyl)prop-2-en-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With sodium tetrahydroborate In methanol for 5h; Heating;
68% With sodium tetrahydroborate; cerium(III) chloride monohydrate In methanol for 1h;
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In tetrahydrofuran at 0 - 20℃;
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol at 20℃; for 0.25h;

  • 9
  • [ 1608-51-1 ]
  • [ 109-77-3 ]
  • [ 89451-46-7 ]
YieldReaction ConditionsOperation in experiment
87% With morpholine; sulfur In ethanol Heating;
With morpholine; sulfur In ethanol for 2h; Heating;
  • 10
  • [ 1608-51-1 ]
  • [ 36635-61-7 ]
  • (4-(4-fluorophenyl)-1H-pyrrol-3-yl)(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydride In tetrahydrofuran at 25℃; for 0.25h;
  • 11
  • [ 3592-47-0 ]
  • Trifluoro-methanesulfonate[(E)-2-(4-fluoro-phenyl)-vinyl]-diphenyl-selenonium; [ No CAS ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
14% With sodium hydride In N,N-dimethyl-formamide at 0℃; for 4h;
  • 12
  • [ 100-52-7 ]
  • 1-fluoro-4-(1-iodovinyl)benzene [ No CAS ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
44% With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 24h;
  • 13
  • [ 2620-63-5 ]
  • [ 1608-51-1 ]
  • 4-(4-fluoro-phenyl)-6-phenyl-1<i>H</i>-pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With caesium carbonate In N,N-dimethyl-formamide at 140℃; for 1h;
  • 14
  • [ 459-57-4 ]
  • [ 536-74-3 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
71% With ytterbium(III) triflate at 90℃; for 12h;
54% With tin(ll) chloride; butan-1-ol In nitromethane at 80℃; for 3h; stereoselective reaction;
Multi-step reaction with 2 steps 1: copper(l) chloride / 0.03 h / Inert atmosphere; Microwave irradiation; Solvent-free 2: montmorillonite clay doped with CuCl; air / 0.17 h / Microwave irradiation; Solvent-free
  • 15
  • [ 1608-51-1 ]
  • [ 17356-08-0 ]
  • [ 380560-03-2 ]
YieldReaction ConditionsOperation in experiment
80% With potassium hydroxide In ethanol for 4h; Heating;
  • 16
  • [ 1608-51-1 ]
  • [ 41865-46-7 ]
YieldReaction ConditionsOperation in experiment
92% With ammonium acetate; zinc In ethanol at 20℃; for 1.25h;
85% With copper nanoparticles on black carbon; water; bis(pinacol)diborane; sodium t-butanolate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; 4.4.10. Experimental procedures for examples described in Table 5. General procedure: Cu NPs/CB (2mg, 1.25mol%), B2(pin)2 (0.22mmol), 1 (0.2mmol) and NaOtBu (0.4 mmol) were added to a 25 mL oven-dried Schlenk tube in air. The tube was evacuated and filled with argon (this procedure was repeated three times). Then H2O (0.8 mmol) and dioxane (2 mL) was added with a syringe under a counter flow of argon. The resulting reaction mixture was stirred at 80 °C for 24 h. The reaction mixture was then diluted with Et2O, filtered through silica gel with copious washings (Et2O or EtOAc), concentrated, and purified by column chromatography.
56% With selenium; potassium acetate In N,N-dimethyl-formamide at 150℃; for 24h; Inert atmosphere; 8 Example 8 Synthesis of 3-(p-fluorophenyl)-1-phenylpropan-1-one: (2E)-3-(p-fluorophenyl)-1-phenylprop-2-en-1-one(0.4 mmol, 1 equiv), selenium powder (1.2 mmol, 3 equiv) and KOAc (0.8 mmol, 2 equiv) Add to the reaction tube,Then, evacuation-nitrogen exchange was performed three times and 2 mL of DMF was added.After stirring at a reaction temperature of 150° C. and monitoring the end of the reaction by TLC (about 24 h), the reaction mixture is cooled and then diluted with ethyl acetate.Distilled under reduced pressure, the product was isolated by column chromatography (eluent: petroleum etherEther was mixed in a volume ratio of 9:1) and the product was a pale yellow solid.Weight 51.1 mg, yield 56%.
40% With hydrogen iodide In o-xylene; water at 145℃; for 8h; chemoselective reaction; General Procedure of the Reduction. 1,2-Diphenylpropan-1-one (3a) General procedure: In a test tube with a screw cap, 1a(0.212 g, 1.02mmol), 57 wt% aq. HI (0.561 g, 2.57mmol), andchlorobenzene (5.0 mL) was added. The mixture was heatedat 110 °C for 8 h. To the reaction mixture was added saturatedNa2S2O3 solution (30 mL), and was extracted CHCl3 (20mL 3). The combined organic layer was dried with Na2SO4.After filtration and evaporation, residue (0.262 g) was obtained.14.1 mg of the residue was combined with p-chlorobenzaldehyde(12.3 mg) as an internal standard. The mixture was thenmeasured with 1H NMR to determine the yield via the integrationof a methine peak of 3a (4.69 ppm) and formyl peak of p-chlorobenzaldehyde(9.98 ppm) (integration ratio = 61.5:100,98% yield). Furthermore, the reaction mixture including pchlorobenzaldehydewas subjected to column chromatographyon SiO2 (n-hexane:EtOAc = 10:1) and recycling preparativeHPLC (n-hexane:EtOAc = 10:1) to give 3a (0.1326 g, 0.631mmol, 62%) as a white solid.
With tris(triphenylphosphine)ruthenium(II) chloride; formaldehyd; water; potassium carbonate In toluene at 110℃; for 18h; Inert atmosphere; Sealed tube; chemoselective reaction;
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h 2: sodium t-butanolate; 1,10-Phenanthroline / toluene / 3 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 0.25 h / 20 °C 2: caesium carbonate / dimethyl sulfoxide / 80 °C / Inert atmosphere
With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; 1.2 General procedure for the preparation of 1,3-diphenylpropan-1-one derivatives General procedure: The chalcone, Pd/C (an amount equal to the quantity of the chalcone) and 30 mL of ethyl acetate were placed into the reactor. The reaction was conducted in an BLT-2000 medium-pressure hydrogenation apparatus for 3.5-4 h and monitored by TLC using 5% ethyl acetate/petroleum ether as the solvent system. When the reaction was finished,the Pd/C was filtered, and the solvent was removed. In most cases, the crudeproduct was purified by column chromatography using ethyl acetate/petroleumether as the solvent system. All the compounds without the spectrum data were obtained as pure productsmonitored by TLC, and the crude products were directly used in the next step.

  • 17
  • [ 1608-51-1 ]
  • [ 57-13-6 ]
  • 7-Fluoro-4-[1-(2-hydroxy-1,4-dihydro-quinazolin-4-yl)-meth-(Z)-ylidene]-1,4-dihydro-quinazolin-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With SbCl3*Al2O3 at 135℃;
  • 18
  • [ 1608-51-1 ]
  • [ 98-80-6 ]
  • 3-(4-fluorophenyl)-3-(4-methoxyphenyl)-1-phenylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: phenylboronic acid With diethylzinc In hexane; toluene at 60℃; for 12h; Stage #2: 4-fluorochalcone In hexane; toluene at 0℃; for 10h;
  • 19
  • [ 75-52-5 ]
  • [ 1608-51-1 ]
  • 3-(4-fluoro-phenyl)-4-nitro-1-phenyl-butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With 1-(3,5-Bis-trifluoromethyl-phenyl)-3-[(R)-quinolin-4-yl-((2R,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-thiourea In toluene at 20℃; for 122h;
  • 20
  • [ 1004-40-6 ]
  • [ 1608-51-1 ]
  • 5-(4-fluorophenyl)-7-phenyl-2-thioxopyrido[2,3-d]pyrimidin-4-one [ No CAS ]
  • 21
  • [ 63636-89-5 ]
  • [ 1608-51-1 ]
  • (E)-3-(4-fluorophenyl)-1-phenyl-N-[(2-pyridyl)sulfonyl]prop-2-en-1-imine [ No CAS ]
  • 22
  • [ 1608-51-1 ]
  • [ 1498-83-5 ]
YieldReaction ConditionsOperation in experiment
78% With urea at 130℃;
  • 23
  • [ 1608-51-1 ]
  • [ 95-54-5 ]
  • 2-(4-fluorophenyl)-4-phenyl-1H,2H,3H-benzo[b]1,4-diazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% at 60℃; for 1.33333h;
  • 24
  • [ 1608-51-1 ]
  • trans-(2R,3S)-2,3-epoxy-3-(4-fluorophenyl)-1-phenylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With Cumene hydroperoxide; 4 A molecular sieve; Triphenylphosphine oxide In tetrahydrofuran at 25℃; for 0.5h;
  • 25
  • [ 35203-91-9 ]
  • [ 1608-51-1 ]
  • (E)-3-(4-fluorophenyl)-1-phenyl-N-[(8-quinoyl)sulfonyl]prop-2-en-1-imine [ No CAS ]
  • 26
  • [ 7677-24-9 ]
  • [ 1608-51-1 ]
  • 2-(4-fluorophenyl)-4-oxo-4-phenylbutanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: trimethylsilyl cyanide; 4-fluorochalcone for 0.0833333h; microwave irradiation; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.0833333h;
  • 27
  • [ 1608-51-1 ]
  • [ 557-20-0 ]
  • [ 586-96-9 ]
  • 3-(4-fluoro-phenyl)-2-(hydroxy-phenyl-amino)-1-phenyl-pentan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 4-fluorochalcone; diethylzinc In hexane; toluene at -20℃; for 3h; Stage #2: Nitrosobenzene In hexane; toluene at -20℃; for 18h;
  • 28
  • [ 1608-51-1 ]
  • [ 137-07-5 ]
  • [ 86602-75-7 ]
YieldReaction ConditionsOperation in experiment
90% In 1,2-dichloro-ethane for 0.666667h; Heating;
79% With sodium dodecyl-sulfate In water at 110℃; for 12h;
  • 29
  • [ 1608-51-1 ]
  • 4-(4-fluorophenyl)-3-[(4-fluorophenyl)methyl]-2,6-diphenylpyridine [ No CAS ]
  • [ 1498-83-5 ]
YieldReaction ConditionsOperation in experiment
1: 67% 2: 29% With urea In chloroform at 130℃; for 0.383333h; microwave irradiation;
  • 30
  • [ 1608-51-1 ]
  • [ 77252-67-6 ]
YieldReaction ConditionsOperation in experiment
With bromine In tetrachloromethane at 20℃;
With potassium carbonate; pyridinium hydrobromide perbromide In dichloromethane at 20℃; for 2h; Inert atmosphere;
  • 31
  • [ 1608-51-1 ]
  • (2R,4S)-4-(4-fluorophenyl)-6-phenyl-2-propoxy-1-[(8-quinolyl)sulfonyl]-1,2,3,4-tetrahydropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 71 percent / Et3N; TiCl4 / CH2Cl2 / Heating 2: Ni(ClO4)2*6H2O; (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) / CH2Cl2 / 72 h / 20 °C
  • 32
  • [ 1608-51-1 ]
  • 4-(p-fluorophenyl)-6-phenyl-2-propoxy-1-[(8-quinolyl)sulfonyl]-1,2,3,4-tetrahydropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 71 percent / Et3N; TiCl4 / CH2Cl2 / Heating 2: Ni(ClO4)2*6H2O; (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) / CH2Cl2 / 72 h / 20 °C
  • 33
  • [ 1608-51-1 ]
  • [ 129122-54-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: EtONa / ethanol / 4.5 h / Ambient temperature 2: NH4OAc, Cu(OAc)2 / acetic acid / 24 h / Heating 3: LiAlH4 / tetrahydrofuran / 6 h / Ambient temperature 4: 87 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / Ambient temperature 5: triphenylphosphine / CH2Cl2 / 0.42 h / Ambient temperature 6: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 30 min 8: H2 / 10percent Pd/C / methanol / 72 h / 2585.7 Torr
  • 34
  • [ 1608-51-1 ]
  • [ 129121-94-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: EtONa / ethanol / 4.5 h / Ambient temperature 2: NH4OAc, Cu(OAc)2 / acetic acid / 24 h / Heating 3: LiAlH4 / tetrahydrofuran / 6 h / Ambient temperature 4: 87 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / Ambient temperature 5: triphenylphosphine / CH2Cl2 / 0.42 h / Ambient temperature 6: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 30 min 8: H2 / 10percent Pd/C / methanol / 72 h / 2585.7 Torr 9: aq. LiOH / dioxane / Heating
  • 35
  • [ 403-42-9 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
73% With sodium methylate; benzaldehyde In ethanol 95.B B. B. 3-(4-Fluorophenyl)-1-phenyl-2-propen-1-one A solution of benzaldehyde (19.220 g, 181 mmol) and p-fluoroacetophenone (25.000 g, 181 mmol) in ethanol (200 ml) was treated with sodium methoxide (1.972 g, 36.5 mmol). A precipitate fell out of solution after 30 minutes. After stirring at room temperature for 15 hours, the solution was treated with 50 ml of H2 O, cooled in an ice bath, and filtered. The solid was rinsed with cold ethanol and dried under high vacuum to yield compound B (29.730 g, 73%) as a yellow crystalline solid. Melting point: 76.3°-77.5° TLC: Rf =0.46 (20% EtOAc in hexane) Microanalysis for C15 H11 FO: Calc'd: C 79.63, H 4.90, F 8.40 Found: C 79.57, H 4.77, F 8.30
With benzaldehyde 1.57 57) 57) Preparation of 4-fluorochalcone 4-fluorochalcone was synthesised according to procedure E using benzaldehyde (0.10 ml, 1.0 mmol) and 4-fluoroacetophenone (0.14 g, 1.0 mmol) as starting materials: Yellow crystals (0.20 g, 90%), mp: 102.1-103.2° C. 1H NMR (CDCl3) δ 8.04 (m, H2', H6'), 7.80 (d, J 15.5 Hz, Hβ), 7.62 (m, H3', H5'), 7.49 (d, J 15.5 Hz, Hα), 7.40 (m, H2, H4, H6), 7.15 (m, H3, H5).13C NMR δ 188.1 (C=O), 168.1 (C4'), 145.0 (Cβ), 134.7 (C1), 134.4 (C1'), 131.0 (C2', C6'), 130.6 (C3, C5), 129.0 (C2, C6), 128.5 (C4), 121.4 (Cα), 115.9 (C3', C5'). Anal. Calcd. (C15H11OF): C, 79.63; H, 4.90. Found: C, 80.01; H, 4.97.
  • 36
  • 3-(4-Fluorophenyl)indan-1-one Polyphosphoric acid [ No CAS ]
  • [ 1608-51-1 ]
  • 3-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water 11.b (a) (b) 3-(4-Fluorophenyl)indan-1-one Polyphosphoric acid (102 g) was heated in an oil bath at 140° C. and 3-(4-fluorophenyl)-1-phenylpropenone (5.9 g) was added. Heating was continued for 30 min at 140° C. The mixture was cooled to 80° C. and water was added carefully. The mixture was extracted with ethyl acetate. The organic extracts were washed with water. After drying over sodium sulfate the solvent was evaporated under reduced pressure. The 3-(4-fluorophenyl)indan-1-one obtained was recrystallized from heptane-ethyl acetate 8:2. 1H NMR (CDCl3): δ 2.64 (1H, dd, 2Jgem=19.2 Hz, 3J=3.9 Hz), 3.23 (1H, dd, 2Jgem=19.2 Hz, 3J=8.1 Hz), 4.57 (1H, dd, 3J=8.0 Hz, 3J=3.9 Hz), 7.00 (2H, distorted t, 3J=8.7 Hz), 7.06-7.11 (2H, m), 7.25 (1H, m), 7.43 (1H, t, Jorto=7.4 Hz), 7.58 (1H, td, Jorto=7.5 Hz, Jmeta=1.2 Hz), 7.82 (1H, d, Jorto=7.7 Hz)
  • 37
  • [ 1608-51-1 ]
  • [ 123837-47-8 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate; acetic acid In ethanol; water 2.A A. A. α-acetyl-β-(4-fluorophenyl)-δ-oxobenzenepentanoic acid, ethyl ester To a mixture of (E)-3-(4-fluorophenyl)-1-phenyl-2-propen-1-one (4.62 gm, 20.4 mmol) (the preparation of which is described in Example 1 and ethyl acetoacetate (5.32 gm, 40.9 mmol) in absolute EtOH (100 ml) was added a solution of EtONa in EtOH. The EtONa solution was prepared by dissolving Na metal (65 mg, 2.8 mmol) in EtOH (10 ml). A precipitate formed after 4 hours of stirring. After 6 hours, the reaction was diluted with a solution of HOAc (170 mg) in H2 O (100 ml), stirred for 5 minutes, then filtered. The solid was washed with H2 O and dried overnight in vacuo to afford α-acetyl-β-(4-fluorophenyl)-δ-oxobenzenepentanoic acid, ethyl ester (6.12 gm) in ~60-65% purity. This material was used directly in the next reaction. TLC: Rf 0.15 (20% EtOAc in hexane)
  • 38
  • concentrated H2 SO4 [ No CAS ]
  • [ 459-57-4 ]
  • [ 98-86-2 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
60% In glacial HOAc 1.A A. A. (E)-3-(4-fluorophenyl)-1-phenyl-2-propen-1-one A mixture of acetophenone (7.02 gm, 58.4 mmol), p-fluorobenzaldehyde (7.24 gm, 58.4 mmol) and concentrated H2 SO4 (10 ml) in glacial HOAc (116 ml) was stirred at room temperature for 2 days. The solution was poured into H2 O (250 ml) and neutralized with 10% NaOH (200 ml). The aqueous layer was extracted once with Et2 O and the Et2 O layer was washed successively with H2 O, saturated NaHCO3 (2*) and brine, then dried (MgSO4). Filtration and removal of the solvent afforded a yellow solid which was recrystallized from hot hexane to give (E)-3-(4-fluorophenyl)-1-phenyl-2-propen-1-one (7.94 gm, 60%) as light yellow needles. m.p. 86°-88° C. TLC: Rf 0.36 (20% EtOAc in hexane)
60% In glacial HOAc 54.A A. A. 3-(4-Fluorophenyl)-1-phenyl-2-propen-1-one A mixture of acetophenone (7.02 gm, 58.4 mmol), p-fluorobenzaldehyde (7.24 gm, 58.4 mmol) and concentrated H2 SO4 (10 ml) in glacial HOAc (116 ml) was stirred at room temperature for 2 days. The solution was poured into H2 O (250 ml) and neutralized with 10% NaOH (200 ml). The aqueous layer was extracted once with Et2 O and the Et2 O layer was washed successively with H2 O, saturated NaHCO3 (twice) and brine, then dried (magnesium sulfate). Filtration and removal of the solvent afforded a yellow solid, which was recrystallized from hot hexane to give the title compound (7.94 gm, 60%) as light yellow needles. m.p. 86°-88° C. TLC: Rf =0.36 (20% EtOAc in hexane) Anal. Calc'd for C15 H11 FO: C 79.63 H 4.90 F 8.40 Found: C 79.76 H 4.95 F 8.50
  • 39
  • [ 1608-51-1 ]
  • 3-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With PPA In water 11.b (b) (b) 3-(4-Fluorophenyl)indan-1-one Polyphosphoric acid (102 g) was heated in an oil bath at 140 °C and 3-(4-fluorophenyl)-1-phenylpropenone (5.9 g) was added. Heating was continued for 30 min at 140 °C. The mixture was cooled to 80 °C and water was added carefully. The mixture was extracted with ethyl acetate. The organic extracts were washed with water. After drying over sodium sulfate the solvent was evaporated under reduced pressure. The 3-(4-fluorophenyl)indan-1-one obtained was recrystallized from heptane-ethyl acetate 8:2. 1H NMR (CDCl3): δ 2.64 (1H, dd, 2Jgem = 19.2 Hz, 3J = 3.9 Hz), 3.23 (1H, dd, 2Jgem = 19.2 Hz, 3J = 8.1 Hz), 4.57 (1H, dd, 3J = 8.0 Hz, 3J = 3.9 Hz), 7.00 (2H, distorted t, 3J = 8.7 Hz), 7.06 - 7.11 (2H, m), 7.25 (1 H, m), 7.43 (1H, t, Jorto = 7.4 Hz), 7.58 (1H, td, Jorto = 7.5 Hz, Jmeta = 1.2 Hz), 7.82 (1H, d, Jorto = 7.7 Hz)
  • 40
  • [ 1117-19-7 ]
  • [ 1608-51-1 ]
  • [ 1012918-98-7 ]
YieldReaction ConditionsOperation in experiment
92% With 4 A molecular sieve In toluene at 25℃; for 7h;
  • 41
  • [ 75-52-5 ]
  • [ 1608-51-1 ]
  • C16H14FNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With quinine-based thiourea In toluene at 25℃; for 122h;
  • 42
  • [ 1608-51-1 ]
  • trans-(2R,3S)-2,3-epoxy-3-(4-fluorophenyl)-1-phenylpropan-1-one [ No CAS ]
  • [ 1020690-77-0 ]
YieldReaction ConditionsOperation in experiment
With tert.-butylhydroperoxide; (1R,3S,4S)-2-azabicyclo<2.2.1>heptane-3-exo-diphenylmethanol In hexane at 20℃; for 144h; optical yield given as %ee; enantioselective reaction;
89 % ee Stage #1: 4-fluorochalcone With C64H78N2O4Yb(1-)*C24H48ClLi2O6(1+) In acetonitrile at 0 - 20℃; for 0.416667h; Schlenk technique; Molecular sieve; Stage #2: With tert.-butylhydroperoxide In decane; acetonitrile at 0℃; for 20h; Schlenk technique; Molecular sieve; Overall yield = 76 %; enantioselective reaction;
50 % ee With C42H66CoN4O2(1+); potassium <i>tert</i>-butylate; dihydrogen peroxide In tert-butyl methyl ether; water at 20℃; for 4h; Inert atmosphere; enantioselective reaction;
50 % ee Stage #1: 4-fluorochalcone With (3S,6S)-3,6-diisobutylpiperazine-2,5-dione In hexane at 20℃; for 0.5h; Stage #2: With dihydrogen peroxide; sodium hydroxide In hexane; water at 20℃; for 72h; Darkness; enantioselective reaction; General procedure for the epoxidation of enones : General procedure: The catalyst (0.01 mmol, 0.1 equiv.) was added to a solution of enones (0.1 mmol) in 0.3 mL of hexanes and stirred at room temperature for 30 minutes. Then, 0.2 mL of a solution of 25% NaOH in 30% hydrogen peroxide (0.25g/mL) was added and the triphasic mixture was stirred in the dark at room temperature for 72h. 25 uL of hydrogen peroxide were added to the solution after each 24 hour period. The conversion and the enantiomeric excess of the corresponding epoxychalcone were determined by chiral HPLC using a Hewlett Packard series 1050. A lower concentration of trans-chalcone in hexanes led to slightly lower enantioselectivities.

  • 43
  • [ 1608-51-1 ]
  • [ 108-59-8 ]
  • [ 1049012-09-0 ]
YieldReaction ConditionsOperation in experiment
54% With (1S,2S)-bis[tris(dimethylamino)phosphazido]-1,2-diphenylethane; lithium perchlorate In dichloromethane; benzene at -40℃; for 48h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 44
  • [ 1608-51-1 ]
  • (E)-N-benzylideneglycine methyl ester [ No CAS ]
  • [ 1100793-81-4 ]
  • methyl 4-benzoyl-3-(p-fluorophenyl)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(acetonitrile)copper(I) perchlorate; (R(P))-2-(tert-butylsulfenyl)-1-(diphenylphosphino)ferrocene; triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 45
  • [ 1608-51-1 ]
  • [ 1020690-77-0 ]
YieldReaction ConditionsOperation in experiment
99% With C33H34N3O2(1+)*Br(1-); dihydrogen peroxide; sodium hydroxide In diethyl ether; toluene at 5℃; for 1h; enantioselective reaction;
85% With Cumene hydroperoxide; diethylzinc; C46H30O4 In Isopropylbenzene; diethyl ether at 20℃; for 4.5h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 46
  • [ 1608-51-1 ]
  • [ 762-04-9 ]
  • [ 1156004-84-0 ]
YieldReaction ConditionsOperation in experiment
99% With diethylzinc; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) In toluene at 0 - 20℃; Inert atmosphere; Molecular sieve; optical yield given as %ee; enantioselective reaction;
  • 47
  • [ 1608-51-1 ]
  • [ 50-01-1 ]
  • [ 84857-13-6 ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydroxide In water for 0.0333333h; Microwave irradiation;
  • 48
  • [ 1608-51-1 ]
  • [ 506-93-4 ]
  • [ 84857-13-6 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide In ethanol for 10h; Reflux;
With sodium hydroxide In ethanol for 10h; Reflux;
  • 49
  • [ 1608-51-1 ]
  • [ 100-53-8 ]
  • (R)-3-benzylthio-3-(4-fluorophenyl)-1-phenylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With C32H28F6N4O3 In toluene at 20℃; for 12h; optical yield given as %ee; enantioselective reaction;
  • 50
  • [ 331984-42-0 ]
  • [ 459-57-4 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
77% With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran optical yield given as %de; stereoselective reaction;
  • 51
  • [ 20913-05-7 ]
  • [ 193675-43-3 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
89% In dimethyl sulfoxide at 100℃; for 12h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
  • 52
  • [ 1608-51-1 ]
  • [ 109-77-3 ]
  • [ 1316231-51-2 ]
YieldReaction ConditionsOperation in experiment
77% With C31H29F3N4O3 In chloroform at 20℃; for 24h; optical yield given as %ee; enantioselective reaction;
  • 53
  • [ 1354381-88-6 ]
  • [ 1608-51-1 ]
  • [ 100-01-6 ]
YieldReaction ConditionsOperation in experiment
1: 78% 2: 70% With montmorillonite clay doped with CuCl; air for 0.166667h; Microwave irradiation; Solvent-free; 4.3. Chemical transformation of fluorinated propargylamines General procedure: Fluorinated propargylamines were mixed with montmorillonite clay doped with CuCl and ground into a ne, homogeneous mixture; then the mixture was put in a 25-mL round bottomed ask and exposed to microwave irradiation at proper power using a microwave oven for an appropriate time. After completion of the reaction (as monitored by TLC), the reaction mixture was diluted with ethyl acetate, and the catalyst and montmorillonite were ltered out. After removal of the solvent under vacuum, the crude material was puried by silica gel column (using petroleum ether:ethyl acetate = 10:1 as elute) to afford chalcones 5[12] or quinoline derivatives 6.
  • 54
  • [ 1354381-99-9 ]
  • [ 1608-51-1 ]
  • [ 99-09-2 ]
YieldReaction ConditionsOperation in experiment
1: 73% 2: 68% With montmorillonite clay doped with CuCl; air for 0.166667h; Microwave irradiation; Solvent-free; 4.3. Chemical transformation of fluorinated propargylamines General procedure: Fluorinated propargylamines were mixed with montmorillonite clay doped with CuCl and ground into a ne, homogeneous mixture; then the mixture was put in a 25-mL round bottomed ask and exposed to microwave irradiation at proper power using a microwave oven for an appropriate time. After completion of the reaction (as monitored by TLC), the reaction mixture was diluted with ethyl acetate, and the catalyst and montmorillonite were ltered out. After removal of the solvent under vacuum, the crude material was puried by silica gel column (using petroleum ether:ethyl acetate = 10:1 as elute) to afford chalcones 5[12] or quinoline derivatives 6.
  • 55
  • [ 98-10-2 ]
  • [ 1608-51-1 ]
  • [ 1401797-51-0 ]
YieldReaction ConditionsOperation in experiment
81% With titanium tetrachloride; triethylamine In dichloromethane at 0℃; Inert atmosphere; Reflux;
  • 56
  • [ 1608-51-1 ]
  • [ 98953-13-0 ]
  • [ 1403750-31-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In ethanol at 80℃; for 5h; General method of synthesis of (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl) methanone(C1-C15) and (2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)methanone (D1-D15) General procedure: Method II Bb (1 mmol) and A (1 mmol) in ethanol (20 mL) were refluxed at 80 C for 5 h with NaOH (0.05 mmol). Then the product was obtained through a column chromatography with mixed eluent (VEtOAc:VPetroleum ether = 5:1). The solvent was evaporated and the separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid.
  • 57
  • [ 1608-51-1 ]
  • [ 90557-92-9 ]
  • [ 1403750-46-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In ethanol at 80℃; for 5h; General method of synthesis of (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl) methanone(C1-C15) and (2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)methanone (D1-D15) General procedure: Method II Bb (1 mmol) and A (1 mmol) in ethanol (20 mL) were refluxed at 80 C for 5 h with NaOH (0.05 mmol). Then the product was obtained through a column chromatography with mixed eluent (VEtOAc:VPetroleum ether = 5:1). The solvent was evaporated and the separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid.
  • 58
  • [ 1608-51-1 ]
  • [ 1611-84-3 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate In ethanol at 80℃; for 5h; General method of synthesis of 3,5-di-substituted-phenyl-4,5-dihydro-1H-pyrazole General procedure: Compound A 5 mmol and 80% hydrazine hydrate (5 mmol) in ethanol (20 mL) were refluxed at 80 C for 5 h. While the reaction completed, the ethanol was evaporated. The separated solid wasfiltered, washed with water and dried to obtain slight yellow solid Ba.
With hydrazine hydrate In toluene at 20℃; for 21h;
With hydrazine hydrate In ethanol for 3h; Reflux; General procedure for synthesis of 3,4-dihydro-3,5-disubstituted pyrazoles 4(a-p) General procedure: The suspension of the corresponding chalcone 3 (440 mg, 2 mmol) and hydrazine hydrate (1.5 mL, 10 mmol) in ethanol (10 mL) was refluxed for 3 h and left overnight at room temperature. The solid precipitate formed was filtered off. The resulting compound obtained was recrystallized from hot ethanol to afford compound 4 as buff crystals.
  • 59
  • [ 583-06-2 ]
  • [ 1765-93-1 ]
  • [ 1608-51-1 ]
  • 60
  • [ 3208-16-0 ]
  • [ 1608-51-1 ]
  • C21H19FO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With boron trifluoride diethyl etherate; In acetonitrile; at 0 - 20℃; for 8h;Inert atmosphere; General procedure: Chalcone 1j (Chalcone 1j was synthesized by condensing equimolar mixture of o-chloro benzaldehyde and acetophenone in methanol with a dropwise addition of 50% NaOH (1 equiv) solution at RT. After completion of the reaction, the reaction mixture was poured into cold water and acidified using 10% HCl solution and the resulting solid product was filtered and dried to offer 1j with a yield of 90%) was reacted with <strong>[3208-16-0]2-<strong>[3208-16-0]ethylfuran</strong></strong> 2 in acetonitrile followed by drop-wise addition of boron trifluoride diethyl etherate at 0 C, The resulting mixture was stirred at room temperature for 8 h under nitrogen atmosphere, the reaction proceeded smoothly and the product was formed as indicated by TLC. After complete consumption of the starting materials, acetonitrile was concentrated by vacuum. The crude compound was extracted with ethyl acetated and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography using silica gel (230:400 mesh) with hexane/ethyl acetate (99:1) as eluent to yield the title compound 3j. Isolated yield: 85%.
  • 61
  • [ 75-89-8 ]
  • [ 1608-51-1 ]
  • 2-(4-fluorophenyl)-1-phenyl-3,3-bis(2,2,2-trifluoroethoxy)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 2,2,2-trifluoroethanol With trimethylsilyl trifluoromethanesulfonate; (2,6-bis(((R)-1-(mesitylamino)-1-oxopropan-2-yl)oxy)-phenyl)-λ3-iodanediyl diacetate In dichloromethane at -40℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 4-fluorochalcone In dichloromethane at -40 - 15℃; for 14.5h; Inert atmosphere; Schlenk technique;
  • 62
  • [ 1608-51-1 ]
  • [ 28871-28-5 ]
  • 2-(4-fluorophenyl)-4-oxo-4-phenylbutanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 4-fluorochalcone; tetraethylammonium cyanide In N,N-dimethyl-formamide at -5 - 0℃; for 0.166667h; Stage #2: With scandium tris(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 0 - 25℃; for 2h; General procedure: The chalcones used in the present study have beenprepared as per literature procedures. TEACN (1 mmol)was dissolved in DMF (30 vol) at room temperature, thencooled to -5 °C to 0 °C. To that, chalcone (1 mmol) wasadded and stirred at -5 °C to 0 °C for 10 min and then,scandium(III) triflate (30% weight of chalcone taken) wasadded at 0 °C, and the reaction mixture was slowly warmedto 25 °C. It was stirred for appropriate time at 25 °Cunder N2 atmosphere. The reaction was monitored by thinlayer chromatography. After completion (about 3 h), thereaction mixture was quenched with water (5 mL) and extractedwith diethyl ether (3 × 10 mL). The combined organiclayer was dried (over anhydrous MgSO4), filtered, concentratedand purified by column chromatography with silicagel (230-400 Mesh) (hexane/ethyl acetate 8:2) to givethe desired product. All the products were characterized by1H and 13C NMR, LCMS, melting point and elementalanalysis. The characterization data for those products thatare not novel are given in the supporting information.
  • 63
  • [ 1608-51-1 ]
  • [ 97693-26-0 ]
  • 2-[5-(4-fluorophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl]-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium hydroxide In ethanol for 72h; Reflux; 4.1.4 General procedure for the preparation of compounds (5a-h) and (6a-h) General procedure: A mixture of compound 3a/3b (4mmol), the appropriate propenone 4a-h (4mmol) and sodium hydroxide (0.2g, 5mmol) in absolute ethanol (30ml) was refluxed for 72h. The reaction mixture was poured on water, neutralized with 2N hydrochloric acid and the residue was filtered off. The crude product obtained was crystallized from isopropanol.
  • 64
  • [ 1608-51-1 ]
  • [ 389614-64-6 ]
  • 4-(4-chlorophenyl)-2-[5-(4-fluorophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl]-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With sodium hydroxide In ethanol for 72h; Reflux; 4.1.4 General procedure for the preparation of compounds (5a-h) and (6a-h) General procedure: A mixture of compound 3a/3b (4mmol), the appropriate propenone 4a-h (4mmol) and sodium hydroxide (0.2g, 5mmol) in absolute ethanol (30ml) was refluxed for 72h. The reaction mixture was poured on water, neutralized with 2N hydrochloric acid and the residue was filtered off. The crude product obtained was crystallized from isopropanol.
  • 65
  • [ 1608-51-1 ]
  • [ 109-77-3 ]
  • [ 137502-97-7 ]
YieldReaction ConditionsOperation in experiment
96% In neat (no solvent) at 80℃; for 0.75h; Sonication; Green chemistry; 2.3 General procedure for synthesis of products (3a-3l) by using ultrasound General procedure: To a mixture of (E)-3-(4-fluorophenyl)-1-(phenyl)prop-2-en-1-one (1 equiv.) and active methylene (1.2 equiv.), ChCl:urea (1:2) (5 equiv.) was added. It was placed under sonication using an ultrasonic horn (ACE horn, 22 kHz frequency) at 40% amplitude for an appropriate time with a 5 s on and 5 s off cycle from time t = 0 h. The reaction progress was monitored on thin layer chromatography (TLC). On completion of the reaction as indicated on TLC, ethyl acetate was added to the reaction mass. Evaporation of the organic layer afforded products which were further purified by column chromatography. For recyclability studies, a deep eutectic mixture was given a wash of ethyl acetate and was used for the next batch and recycled again.
94% With Thermomyces lanuginosus lipase immobilized on the surface of Fe3O4/ZnO core/shell magnetic nanoparticles In 2,2,4-trimethylpentane at 40℃; for 1h; Enzymatic reaction; 8.1 2.7. General procedure for Michael addition of active methylene compounds to chalcones General procedure: Immobilized forms of TLL and some commercially available lipases were used as biocatalyst for the Micheal reaction of active methylene compounds to chalcones. Lipase (300 U) was added to a solution of 0.25 M chalcone and 0.3 M of active methylene compounds in the presence of solvent. The suspension was incubated at 40 °C under magnetic stirring for 1 h. After completion of the reaction (confirmed by TLC), the enzyme was separated from the reaction mixture. The solvent was evaporated under reduced pressure using a rotatory evaporator. The crude residue was purified by thin layer chromatography in n-hexane/ethyl acetate (4:1) as the eluent. The structure of products was characterized by IR and 1H NMR spectroscopy (Bruker AVANCE 300, BrukerBiospin, Rheinstetten, Germany) at 300.13 MHz, in CDCl3. Melting points were measured on an Electrothermal 9100 apparatus and are uncorrected. Enantiomeric excess of the Michael adducts was determined by HPLC apparatus consisted of a Knauer model smart line pump 10,000 and a K-2600 UV variable-wavelength detector with a chiral column (Daicel Chiralpak AD) using n-hexane/isopropanol as a solvent. Experiments were performed independently three times, and error bars represent one standard deviation from the mean. Reusability of the immobilized lipase in the Michael addition reaction was also examined.
  • 66
  • [ 75-52-5 ]
  • [ 1608-51-1 ]
  • [ 1021867-75-3 ]
YieldReaction ConditionsOperation in experiment
96% In neat (no solvent) at 80℃; for 0.666667h; Sonication; Green chemistry; 2.3 General procedure for synthesis of products (3a-3l) by using ultrasound General procedure: To a mixture of (E)-3-(4-fluorophenyl)-1-(phenyl)prop-2-en-1-one (1 equiv.) and active methylene (1.2 equiv.), ChCl:urea (1:2) (5 equiv.) was added. It was placed under sonication using an ultrasonic horn (ACE horn, 22 kHz frequency) at 40% amplitude for an appropriate time with a 5 s on and 5 s off cycle from time t = 0 h. The reaction progress was monitored on thin layer chromatography (TLC). On completion of the reaction as indicated on TLC, ethyl acetate was added to the reaction mass. Evaporation of the organic layer afforded products which were further purified by column chromatography. For recyclability studies, a deep eutectic mixture was given a wash of ethyl acetate and was used for the next batch and recycled again.
  • 67
  • [ 1608-51-1 ]
  • [ 105-56-6 ]
  • ethyl (2RS,3RS)-4-benzoyl-2-cyano-3-(4-fluorophenyl)butyrate [ No CAS ]
  • ethyl 2-cyano-3-(4-fluorophenyl)-5-oxo-5-phenylpentanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In neat (no solvent) at 80℃; for 1.25h; Sonication; Green chemistry; Optical yield = 33.9 %de; 2.3 General procedure for synthesis of products (3a-3l) by using ultrasound General procedure: To a mixture of (E)-3-(4-fluorophenyl)-1-(phenyl)prop-2-en-1-one (1 equiv.) and active methylene (1.2 equiv.), ChCl:urea (1:2) (5 equiv.) was added. It was placed under sonication using an ultrasonic horn (ACE horn, 22 kHz frequency) at 40% amplitude for an appropriate time with a 5 s on and 5 s off cycle from time t = 0 h. The reaction progress was monitored on thin layer chromatography (TLC). On completion of the reaction as indicated on TLC, ethyl acetate was added to the reaction mass. Evaporation of the organic layer afforded products which were further purified by column chromatography. For recyclability studies, a deep eutectic mixture was given a wash of ethyl acetate and was used for the next batch and recycled again.
  • 68
  • [ 147531-11-1 ]
  • [ 1608-51-1 ]
  • [ 921932-52-7 ]
YieldReaction ConditionsOperation in experiment
17% With copper In water; dimethyl sulfoxide at 60℃; for 12h; Inert atmosphere; regioselective reaction; General procedure for the copper mediated conjugate trifluoromethylation General procedure: A stirred solution of α,β-unsaturated ketones 1 (0.20 mmol), trifluoromethylsulfonium triflate 3a (323 mg, 0.80 mmol, 4.0 equiv) and Cu (76.3 mg, 1.20 mmol, 6.0 equiv) in DMSO/H2O (1:1, 1.0mL) was heated at 60 °C for 12 h. After cooling down to room temperature, the reaction mixture was extracted with Et2O, and the combined organic layers was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silicagel to give β-trifluoromethylated ketone 2.
  • 69
  • [ 109-99-9 ]
  • [ 35193-63-6 ]
  • [ 1608-51-1 ]
  • C39H31BrFO6P [ No CAS ]
  • 70
  • [ 1522-41-4 ]
  • [ 1608-51-1 ]
  • [ 130739-86-5 ]
YieldReaction ConditionsOperation in experiment
92% With caesium carbonate In acetonitrile at 70℃; for 0.5h;
  • 71
  • [ 1522-41-4 ]
  • [ 1608-51-1 ]
  • [ 1316191-13-5 ]
YieldReaction ConditionsOperation in experiment
93% With caesium carbonate In acetonitrile at 120℃; for 4h;
  • 72
  • [ 459-32-5 ]
  • [ 611-73-4 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
70% With dipotassium peroxodisulfate; sodium formate; iron(II) chloride In dimethylsulfoxide-d6; water at 120℃; for 15h; Schlenk technique; Inert atmosphere;
  • 73
  • [ 3406-03-9 ]
  • [ 15894-04-9 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
64% With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; copper(ll) bromide In toluene at 100℃; for 18h; (E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one (2c) General procedure: Representative procedure for the reaction of thiols and sulfones: A mixture of benzyl mercaptan 1a (87 µl, 0.75 mmol), copper bromide (II) (1.1 mg, 0.005 mmol), 1,5,7-triazabicyclo[4,4,0]dec-5-ene (53.2 mg, 0.375 mmol) and 1-phenyl-2-(phenylsulfonyl)ethanone 1b (65.1 mg, 0.25 mmol) in toluene (1 M, 0.25 ml) was taken in a 5 ml round bottom flask and stirredat 100 °C for 18 h under oxygen atmosphere. The reaction mixture was evaporated and purified by flash silica gel column chromatography using 1 % ether/hexane to obtain 1c (38.2 mg, 73 %).
  • 74
  • [ 352-34-1 ]
  • [ 936-59-4 ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
91% With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 - 90℃; under 750.075 Torr; for 16h;Inert atmosphere; General procedure: A mixture of Pd(OAc)2 (4.5 mg, 0.02 mmol), PPh3 (11.2 mg, 0.04 mmol), iodobenzene (1a) (82 mg, 0.4mmol), <strong>[936-59-4]3-chloropropiophenone</strong> (2a) (87 mg, 0.5 mmol), and K2CO3 (166 mg, 1.2 mmol) in DMF (2.5 mL) was stirred under a N2 atmosphere at room temperature for 10 min, and then heated at 90 C for 16 h. The reaction was then cooled to ambient temperature and diluted with CH2Cl2 (10 mL) before being filtered through a short pad of silica gel. The silica pad was rinsed with DCM (5 mL), and the combined filtrates were washed with brine (15 mL), dried over anhydrous Na2SO4. The solvent was then removed under reduced pressure to give the crude product as a residue, which was purified by silica gel column chromatography eluting with a mixture of petroleum ether (60-90 C)/EtOAc (v/v = 30:1).
  • 75
  • [ 1608-51-1 ]
  • [ 250285-32-6 ]
  • 3-(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)-1-phenyl-3-(4-fluorophenyl)-1-phenylpropane-1,2-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride With potassium <i>tert</i>-butylate In tetrahydrofuran at 25℃; for 0.166667h; Inert atmosphere; Stage #2: 4-fluorochalcone In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; Stage #3: In tetrahydrofuran for 2h;
  • 76
  • [ 928-49-4 ]
  • [ 1608-51-1 ]
  • 1-((1E,4E)-4-ethyl-1-phenylhepta-1,4-dien-3-yl)-4-fluorobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With titanium(IV) isopropylate; triethylsilane; Ni(bis(4-methylphenyl)imidazolium chloride)(methyl methacrylate)<SUB>2</SUB> In toluene at 65℃; for 8h; Inert atmosphere;
  • 77
  • C15H11FO2 [ No CAS ]
  • [ 1608-51-1 ]
YieldReaction ConditionsOperation in experiment
95% With sodium iodide; tin(ll) chloride In ethanol for 0.0833333h; Reflux; Green chemistry; General procedure for De oxygenation of aliphatic and aromatic epoxide, chalcone epoxide, nitro styrene epoxide and nitrochromene epoxide by novel SnCl 2 / NaI reagent: General procedure: To a solution epoxide (1mmol) and NaI (3mmol) in absolute alcohol (5ml), SnCl2 (2mmol) was added in a several portions. The mixture was stirred at reflux temperature and the progress of reaction was monitored by TLC. Within 2-10 min the reaction mixture is poured in ice-water, precipitation obtained, stirred for 10 min and filtered the solid, dried to obtained pure products 2a-12a/ 1b-17b/1c-10c and 1d- 10d with 85-96% yield.
  • 78
  • [ 1608-51-1 ]
  • [ 918417-74-0 ]
YieldReaction ConditionsOperation in experiment
33% Stage #1: 4-fluorochalcone With Porcine pancreas lipase type II In toluene at 20℃; for 1h; Enzymatic reaction; Stage #2: With pyrrolidine In toluene for 72h; Enzymatic reaction; General Procedure for Lipase-Catalyzed Michael Addition of Acetophenone to Chalcone Derivatives (4a-d). General procedure: To a mixture of 4-chlorochalcone (0.2 mmol, 0.048 g) in 20 mL toluene, 200 mg of PPL was added. The reaction mixture wasstirred for 1 h. Then 0.2 mL pyrrolidine was added and the mixture stirred for a further 72 h after filtration from solid PPL. Theproduct was purified by thin-layer chromatography.
  • 79
  • [ 1608-51-1 ]
  • [ 89-25-8 ]
  • (S)-4-(4-Fluorophenyl)-3-methyl-1,6-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 4-fluorochalcone; edaravone With 9-epi-9-amino-9-deoxyquinine; Boc-D-Phg-OH In dichloromethane at 20℃; for 48h; Stage #2: With Eaton’s reagent at 20℃; for 12h; enantioselective reaction;
  • 80
  • [ 3262-89-3 ]
  • [ 1608-51-1 ]
  • (R)-3-(p-fluorophenyl)-1,3-diphenylpropan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With copper(I) trifluoromethanesulfonate * 1/2 toluene; (Ss,1S,1'S)-N-(1-cyclohexylethyl)-N-(1-tetralinyl)-1,1'-spirobiindan-2,2'-diylphosphoramidite; potassium acetate In toluene at 70℃; for 30h; Inert atmosphere; Autoclave; Glovebox; enantioselective reaction;
  • 81
  • [ 1044569-46-1 ]
  • [ 1608-51-1 ]
  • 1-(2-(3-(4-fluorophenyl)-1-phenylallylidene)hydrazinyl)phthalazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With acetic acid In ethanol for 30h; Reflux; 3 General procedure for the preparation of compounds (10a-f) General procedure: A mixture of equimolar amounts of 1-hydrazinylphthalazine 4 and the appropriate chalcone 9a-f (4mmol) in absolute ethanol (10ml) containing glacial acetic acid (2.5ml) was heated under reflux for 30h. Upon cooling, the separated solid was filtered off and crystallized from acetonitrile. 4.1.6.3 1-(2-(3-(4-Fluorophenyl)-1-phenylallylidene)hydrazinyl)phthalazine (10c) M.p. 198-203 °C, yield: 74%. IR νmax cm-1: 3298 (NH), 3035 (aromatic CH), 2925 (aliphatic CH). 1H NMR (CDCl3): 400 MHz, δ = 6.91 (d, 1H, J = 16.6 Hz, N=C-CH=CH), 7.07 (t, 2H, J = 8.3 Hz, Ar-H), 7.48-7.53 (m, 3H, Ar-H), 7.53-7.58 (m, 3H, Ar-H), 7.67-7.74 (m, 4H, Ar-H), 7.80 (s, 1H, CH-4 phthalazine), 8.17 (d, 1H, J = 16.7 Hz, N=C-CH=CH), 8.56 (d, 1H, J = 7.7 Hz, CH-8 phthalazine), 10.73 (s, 1H, NH, exchanged by D2O). 13C NMR (100 MHz) δ = 115.6, 115.8, 120.2, 120.3, 124.3, 126.1, 127.2, 127.4, 128.2, 128.9, 129.0, 129.4, 131.6, 132.0, 133.2, 133.24, 137.3 (aromatic Cs), 138.3 (N=C-CH=CH), 138.4 (C-4 phthalazine), 148.1 (C-1 allylidene), 160.4 (C-4 flourophenyl), 164.3 (C-1 phthalazine). Anal. Calcd. for C23H17FN4 (368.42): C, 74.98; H, 4.65; N, 15.21. Found: C, 75.12; H, 4.72; N, 15.34.
  • 82
  • [ 5100-57-2 ]
  • [ 1608-51-1 ]
  • ethyl 1-benzoyl-2-(4-fluorophenyl)pyrrolo[1,2-a]quinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With copper diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 75℃; for 18h;
  • 84
  • [ 4149-06-8 ]
  • [ 1608-51-1 ]
  • 4-(4-fluorophenyl)-2,6-diphenyl-1H-pyrazolo[3,4-b]pyridin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With toluene-4-sulfonic acid; In water; acetonitrile; at 80℃; General procedure: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), <strong>[4149-06-8]3-amino-1-phenyl-1H-pyrazol-5(4H)-one</strong> 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.
  • 85
  • [ 1608-51-1 ]
  • [ 73183-34-3 ]
  • 3-(4-fluorophenyl)-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With methanol; copper nanoparticles on black carbon In toluene at 20℃; for 4h; 4.4.9. Experimental procedures for examples described in Table 2 CuNPs/CB (2 mg, 1.25 mol %), B2(pin)2 (0.22 mmol), 1 (0.2 mmol) were added to a 25 mL oven-dried Schlenk tube in air. Then toluene (1 mL) was added with a syringe. The resulting reaction mixture was stirred at room temperature for 4 h. The reaction mixture was then diluted with Et2O, filtered through silica gel with copious washings (Et2O or EtOAc), concentrated, and purified by column chromatography.
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