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[ CAS No. 718-08-1 ] {[proInfo.proName]}

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Chemical Structure| 718-08-1
Chemical Structure| 718-08-1
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Product Details of [ 718-08-1 ]

CAS No. :718-08-1 MDL No. :MFCD03844818
Formula : C12H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BOZNWXQZCYZCSH-UHFFFAOYSA-N
M.W : 206.24 Pubchem ID :225855
Synonyms :

Calculated chemistry of [ 718-08-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.93
TPSA : 43.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 2.22
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 2.68
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.789 mg/ml ; 0.00383 mol/l
Class : Soluble
Log S (Ali) : -2.77
Solubility : 0.354 mg/ml ; 0.00172 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.64
Solubility : 0.0469 mg/ml ; 0.000228 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 718-08-1 ]

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

Application In Synthesis of [ 718-08-1 ]

* 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 [ 718-08-1 ]

[ 718-08-1 ] Synthesis Path-Downstream   1~57

  • 3
  • [ 290-87-9 ]
  • [ 718-08-1 ]
  • [ 72676-86-9 ]
  • 4
  • [ 718-08-1 ]
  • [ 118856-11-4 ]
  • 6
  • [ 623-73-4 ]
  • [ 122-78-1 ]
  • [ 718-08-1 ]
YieldReaction ConditionsOperation in experiment
6.00 g With tin(II) chloride dihdyrate; In dichloromethane; for 2h; To a suspension of SnCI2.2H20 (1.409 g, 6.2 mmol) and ethyl 2-diazoacetate (8.55 g, 74.9 mmol) in DCM (80 ml) was added dropwise 2-phenylacetaldehyde (7.5 g, 62.4 mmol). After 2h of stirring, the suspension was filtered and diluted with a brine solution. The organic phase was separated, dried over anhydrous MgSO4, filtered and the solvent removed under vacuum. The residue was purified on ISCO with a RediSep column using Hex-EA (0-40%) to yield 6.OOg of the title compound. 1H NMR (400 MHz, ODd3) oe ppm 1.26 (t, J=7.04 Hz, 3 H) 3.44 (5, 2 H) 3.83 (5, 2 H) 4.17 (q, J=7.30 Hz, 2 H) 7.10- 7.38 (m, 5 H).
  • 7
  • [ 718-08-1 ]
  • [ 107-91-5 ]
  • [ 183118-95-8 ]
YieldReaction ConditionsOperation in experiment
91% General procedure: A suspension of potassium hydroxide (5.6 g, 0.10 mol, 1 equiv) in ethanol (50 mL) was added slowly to a solution of beta-keto-ester 1 (0.10 mol, 1 equiv) and cyano-acetamide (0.10 mol, 1 equiv) in EtOH (50 mL). The mixture was stirred at reflux for 18 h. After cooling down, the formed precipitate was filtered off and made soluble in warm water (200 mL). Thereafter the solution was acidified using 30 mL of a solution of 4 N HCl giving a white precipitate which was filtered off and washed with water and cold diethyl ether. The solid residue was dried in vacuum to yield the desired substituted pyridine as a white powder. No further purification was needed.Compounds 2a and 2b are commercially available.
  • 8
  • [ 718-08-1 ]
  • [ 18257-46-0 ]
  • [ 223927-13-7 ]
  • 9
  • [ 718-08-1 ]
  • 3-hydroxy-5-benzyl-1H-pyrazole [ No CAS ]
  • 10
  • [ 2033-24-1 ]
  • [ 64-17-5 ]
  • [ 103-80-0 ]
  • [ 718-08-1 ]
YieldReaction ConditionsOperation in experiment
38% A. Ethyl 3-oxo-4-phenylbutanoate [00199] To a solution of phenylacetyl chloride (1 mL, 7.56 mmol) was added dropwise a solution of 2,2-dimethyl-l,3-dioxane-4,6-dione (1.09 g, 7.56 mmol) and pyridine (1.3 mL) in CH2CI2 (20 mL) at 0 C. The solution was stirred for 30 min at 0 C, then allowed to warm slowly to rt and stirred overnight. The reaction mixture was then washed with 10% aqueous HC1 (2 x 10 mL). The organic layer was dried (MgS04), filtered, and concentrated under reduced pressure. The crude residue was dissolved in EtOH (20 mL) and heated under reflux conditions for 4 h. The mixture was cooled to rt and then concentrated under reduced pressure. The resulting oil was purified by flash column chromatography (PE/EA = 1/4) to afford the title compound (600 mg, 38%) as a yellow oil. [M+H] Calc'd for Ci2Hi403, 207; Found, 207.
  • 11
  • [ 718-08-1 ]
  • [ 444613-61-0 ]
YieldReaction ConditionsOperation in experiment
86% With sulfuryl dichloride; In dichloromethane; at 20℃; for 1h; Reference Example 2: Production of ethyl 2-chloro-3-oxo-4-phenylbutyrate Ethyl 3-oxo-4-phenylbutyrate (4.8 g, 23 mmol) and methylene chloride (48 ml) were mixed, and sulfuryl chloride (3.1 g, 1 equivalent) was gradually added thereto dropwise. After the addition, the mixture was stirred at 20C for 1 hour. The reaction mixture was concentrated under reduced pressure, and saturated aqueous solution of sodium hydrogencarbonate (10 ml) was added, and extraction was carried out with ethyl acetate (20 ml). The solvent was evaporated away under reduced pressure and drying was carried out in vacuum to obtain the title compound as a yellow oil (4.8 g, yield: 86 %).
  • 12
  • [ 718-08-1 ]
  • [ 88284-48-4 ]
  • ethyl 2-(2-(2-phenylacetyl)phenyl)acetate [ No CAS ]
  • 13
  • [ 718-08-1 ]
  • [ 188475-11-8 ]
YieldReaction ConditionsOperation in experiment
With 4-acetamidobenzenesulfonyl azide; triethylamine; In dichloromethane; at 0 - 20℃; Compound P1 (5.4 g, 26.18 mmol) and 4-acetamidobenzenesulfonyl azide (6.29, 1 eq) were dissolved in CH2CI2 (131 ml) at 0 0C, Et3N (109 ml, 3 eq) was added and the mixture stirred at room temperature for 1 hour. The precipitate that was formed was removed by filtration and the filtrate concentrated under reduced pressure to give an oil that was purified by silica gel chromatography (SGC, 0-10% EtOAc in hexane) to give 4.9 g of P2.
  • 14
  • [ 718-08-1 ]
  • [ 6728-72-9 ]
YieldReaction ConditionsOperation in experiment
59% With platinum(IV) oxide; hydrogen; triethylamine; In ethanol; at 50℃; under 2585.81 Torr; The reaction was set into two batches and the work-up was combined together.To the solution of compound 43-B (50 g, 0.243 mol, 1.0 eq) and TEA (0.2 mL) in 400 mL of EtOH was added Pt02(636 mg, 2.43 mmol, 0.01 eq) under Ar atmosphere. The reaction mixture was degassed with Ar for 3 times and H2for 3 times. Then the mixture was stirred at 50C under H2(50 psi). TLC (PE: EA = 5: 1) showed compound 43-B remained about 30%. The mixture was filtered through a pad of celite, the pad was washed with EtOAc (300mL x 2). The combined filtrate was concentrated and purified by column chromatography on silica gel (PE: EA = 100: 1-80:1-50: 1) to supply compound 43-C (60 g, 59% yield) as yellow liquid.^NMR: (400 MHz, CDCI3) delta: 7.36 - 7.15 (m, 1H), 4.31 - 4.22 (m, 1H), 4.15 (q, = 7.1 Hz, 2H), 2.99 (d, = 3.3 Hz, 1H), 2.92 - 2.83 (m, 1H), 2.80 - 2.73 (m, 1H), 2.56 - 2.39(m, 2H), 1.26 (t, = 7.2 Hz, 3H).
  • 15
  • [ 718-08-1 ]
  • [ 5154-00-7 ]
  • C15H12N2O2 [ No CAS ]
  • 16
  • [ 718-08-1 ]
  • 4-acetyl-2-iodotrifluoroacetanilide [ No CAS ]
  • ethyl 5-acetyl-2-benzyl-1H-indole-3-carboxylate [ No CAS ]
  • 17
  • [ 718-08-1 ]
  • [ 940299-78-5 ]
  • ethyl 5-acetyl-2-benzyl-1H-indole-3-carboxylate [ No CAS ]
  • 18
  • [ 103-80-0 ]
  • [ 718-08-1 ]
YieldReaction ConditionsOperation in experiment
67% a Ethyl 3-oxo-4-phenylbutanoate Following the procedure described in reference example 15a, but using phenylacetyl chloride instead of cyclopropanecarbonyl chloride, the desired product was obtained as a colourless oil in 67% yield. 1 H-NMR-(CDCl3) delta (TMS): 1.25 (t, J=7.2 Hz, 3H), 3.43 (s, 2H), 3.82 (s, 2H), 4.17 (q, J=7.2 Hz, 2H), 7.28 (m, 5H).
  • 19
  • [ 718-08-1 ]
  • [ 59554-14-2 ]
  • 20
  • [ 718-08-1 ]
  • [ 67839-63-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 45 percent / KOH / ethanol / 24 h / Heating 2: 91 percent / POCl3, Et3N / 17 h / 140 °C 3: 75 percent / H2, NaOAc / 5percent Pd/C / methanol / 760 Torr / Ambient temperature
  • 21
  • [ 718-08-1 ]
  • [ 51-79-6 ]
  • [ 106013-88-1 ]
YieldReaction ConditionsOperation in experiment
83% With trichlorophosphate; at 90℃; for 3h;Heating / reflux; ethyl 2-phenylacetoacetate (1.0 g, 4.85 mmol) and urethane (0.43 g, 4.85 mmol) were heated, neat, with phosphorous oxychloride (3 ML) at 90 C. for 3 hours.The excess reagents were removed under vacuum and the resulting residue was triturated with benzene and filtered.This solid was triturated with diethyl ether, filtered, and dried to yield 0.818 g (83%). MS (DCI/NH3) m/z 204 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 1.98 (s, 3 H) 7.28 (m, 2 H) 7.39 (m, 3 H) 11.65 (s, 1 H).
  • 22
  • [ 141-97-9 ]
  • [ 103-80-0 ]
  • [ 718-08-1 ]
YieldReaction ConditionsOperation in experiment
66% With sodium chloride; sulfuric acid; sodium hydrogencarbonate; In ethanol; water; toluene; EXAMPLE 16 Synthesis of ethyl 4-phenyl-3-oxobutanoate: To 200 ml of toluene was added 40.0 g of barium oxide (purity: 90%, 0.235 mol). After adding 0.5 ml of water and activating under vigorously stirring, 104.1 g (0.8 mol) of ethyl acetoacetate was dropped thereinto at 20 to 30 C. over 1 hour. Then stirring was continued for 1 hour. Into the obtained solution was dropped 30.9 g (0.2 mol) of phenylacetyl chloride at 20 to 30 C. over 1 hour and stirring was continued for additional 1 hour. Next, 21.7 g (0.47 mol) of ethanol was added to the reaction mixture which was then stirred for 16 hours. After adjusting the pH value of the reaction mixture to 1 by adding dilute sulfuric acid, the insoluble barium salt was filtered off. After separating out, the toluene layer was washed with a 5% aqueous solution of sodium hydrogencarbonate and a 5% aqueous solution of sodium chloride. After distilling off the toluene under reduced pressure, 95.7 g of an oily product was obtained. 48.1 g of the ethyl acetoacetate was recovered by distillation under reduced pressure. Then 30.9 g of ethyl 4-phenyl-3-oxobutanoate was obtained (b.p.: 125-130 C./0.6 mmHg, GC purity: 88%) at a yield of 66%. The physical data of this product are as follows. 1 H-NMR (CDCl3, delta ppm): 1.24 (3H, t, J=7.1 Hz), 3.44 (2H, s), 3.82 (2H, s), 4.16 (2H, q, J=7.1 Hz), 7.20-7.35 (5H, m).
  • 23
  • [ 6148-64-7 ]
  • [ 532-27-4 ]
  • [ 718-08-1 ]
YieldReaction ConditionsOperation in experiment
86% Reference Example 1: Production of ethyl 3-oxo-4-phenylbutyrate Monoethyl monopotassium malonate (12.9 g, 2.3 equivalents) was mixed with tetrahydrofuran (200 ml), and the mixture was cooled to 5C. Triethylamine (8.2 g, 2.5 equivalents) and magnesium chloride (8.62 g, 2.8 equivalents) were added, and the mixture was stirred at 5 to 20C for 3 hours. The reaction mixture was cooled to 5C. Phenacyl chloride (5 g, 32 mmol, 1 equivalent) was gradually added, and the mixture was stirred at 5 to 20C for 63 hours. The mixture was cooled to 5C, and 1 N hydrochloric acid (30 ml) was added. Tetrahydrofuran was evaporated away under reduced pressure, and extraction was carried out with ethyl acetate (50 ml). The organic layer was washed with 1 N hydrochloric acid (30 ml), water (10 ml), saturated aqueous solution of sodium hydrogencarbonate (30 ml) and water (10 ml) in order. The solvent was evaporated away under reduced pressure to obtain the title compound as a pale yellow oil (5.82 g, yield: 86 %).
  • 24
  • [ 718-08-1 ]
  • 3-((4-methoxyphenyl)ethynyl)-4H-chromen-4-one [ No CAS ]
  • [ 1190871-29-4 ]
  • 25
  • [ 98-01-1 ]
  • [ 718-08-1 ]
  • [ 27861-39-8 ]
  • ethyl 5-cyclohex-1-enyl-4-(furan-2-yl)-4,5-dihydro-2-phenylfuran-3-carboxylate [ No CAS ]
  • 26
  • [ 718-08-1 ]
  • [ 5349-17-7 ]
  • C19H18N2O2 [ No CAS ]
  • 27
  • [ 718-08-1 ]
  • [ 57297-29-7 ]
  • [ 1258306-10-3 ]
  • 28
  • [ 718-08-1 ]
  • [ 49845-33-2 ]
  • [ 1297502-81-8 ]
YieldReaction ConditionsOperation in experiment
53% General procedure: A 10 mL round-bottom flask was charged with a magnetic stirrer, THF (2 mL), ethyl benzoylacetate (192 mg, 1 mmol), and NaH (26 mg, 1.1 mmol), after stirring of the mixture for 15 min at rt, the mixture was cooled down to -50 C. Then 2,4-dichloro-5-nitropyrimidine (194 mg, 1 mmol) in 1 mL of THF was added. The mixture was stirred at -50 C for 3 h (TLC determination), then when warmed to rt, Fe powder (3.0 equiv) and 3 mL of AcOH were added. The mixture reacted for 3 h at 70 C. The resulting mixture was cooled to rt and filtered. The solid was washed with methanol two times (2×3 mL), and the combined filtrate was concentrated on the rotary evaporator, and the residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (3:1, v/v)as the eluent to give the desired product 5a (pale yellow solid, 184 mg, 61%).
  • 29
  • [ 718-08-1 ]
  • [ 708-06-5 ]
  • [ 1314117-08-2 ]
YieldReaction ConditionsOperation in experiment
91% With piperidine; acetic acid; In ethanol; for 5h;Reflux; General procedure: Catalytic amounts of piperidine and acetic acid were added to a mixture of 2-hydroxy-1-naphthaldehyde (2.15 g, 12.5 mmol) and 3-oxo-3-thiophen-3-yl-propionic acid ethyl ester (2.97 g, 14.9 mmol) in dry ethanol (66 mL). The solution was then stirred at reflux temperature for 5 h. After completion of the reaction, the cooled suspension was filtered off and the crude yellow solid was purified by recrystallization.
  • 30
  • [ 718-08-1 ]
  • [ 104-94-9 ]
  • [ 1383986-91-1 ]
YieldReaction ConditionsOperation in experiment
56% With toluene-4-sulfonic acid; In ethanol;Reflux; General procedure: A mixture of beta-ketoester (10 mmol), amine (1.1-1.5 equiv, specified for each compound) and p-TsOH (0.1 mmol) in ethanol (25 mL) was heated at reflux for overnight. The mixture was then cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel with eluents as noted to give the beta-enamino ester.
  • 31
  • [ 718-08-1 ]
  • [ 4930-98-7 ]
  • [ 140397-87-1 ]
YieldReaction ConditionsOperation in experiment
30.8% In ethanol; at 50℃; for 1.5h; Step 2: Synthesis of 3-benzyl-1-(pyridin-2-yl)-1H-pyrazol-5-ol (3a) Compound 2a (1.03 g, 5.0 mmol) prepared in Step 1 of Example A-1 was charged in a 25 mL round-bottom flask and dissolved in 6 mL of ethanol. A solution of 2-hydrazinopyridine (0.55 g, 5.0 mmol, manufactured by Aldrich) in 5 mL of ethanol at 50 C. was gradually added thereto over 30 minutes, followed by reaction for 1 hour. After completion of the reaction was confirmed by TLC, the reaction solution was concentrated by evaporation, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and then purified by column chromatography [n-Hex/EtOAc=3/1 (v/v)] to afford a compound of 3-benzyl-1-(pyridin-2-yl)-1H-pyrazol-5-ol (3a). Yield: 30.8% 1H NMR (300 MHz, DMSO-d6) delta 12.36 (br, 1H) 8.44-8.41 (m, 1H), 7.98-7.94 (m, 2H), 7.32-7.20 (m, 6H), 5.25 (br, 1H), 3.86 (s, 2H); EIMS m/z (rel intensity) 251 (M+, 100), 159 (82), 129 (11).
  • 32
  • [ 718-08-1 ]
  • [ 74-88-4 ]
  • [ 2867-62-1 ]
YieldReaction ConditionsOperation in experiment
85.6% Synthesis 2-methylphenylacetoacetic acid ethyl ester, to a dried 250ml four-necked flask was added 50g of phenylacetoacetic acid ethyl ester, 150g DMF, 50g ground potassium carbonate, stirred for 0.5 hours at room temperature, warmed to 40 C, a solution of 41. 3g methyl iodide and 50g DMF was added dropwise to the mixture, after addition was completed, warmed to 60-65 C under insulation for 3h, to the GC no raw material, cooling, Poured with 2L of ice water, extracted using 800ml EA ,revolving off EA, obtained 45. 7g brown liquid ,yield 85.6%, purity:. 95 2% (GC).
84.3% To a dried 250 ml three-necked flask was added ethyl 3-oxo-4-phenyl-butanoate (4.00 g, 19.4 mmoL), THF (50.0 mL), sodium hydride (931 mg, 23.3 mmoi) and the reaction stirred for 0.5 hours at 0C. A solution of methyl iodide (3.03 g, 21.3) was next added drop-wise. After addition was completed, the reaction mixture was warmed to 20 C and stirred for two hours at 20C. The reaction mixture was quenched by addition of water (10.0 mL) at 20 C and then diluted with ethyl acetate (20.0 mL) and the layers separated. The aqueous layer was next extracted with ethyl acetate (20.0 mL chi 3). The combined organic layers were washed with brine (30.0 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, Petroleum ether : Ethyl acetate 20: 1 to 10: 1) to give ethyl 2-methyl-3-oxo-4-phenyl-butanoate (3.60 g, 16.3 mmol, 84.3% yield) as a colorless oil. NMR (400 MHz, CDCh) delta = 7.38 - 7.28 (m, 3H), 7.25 - 7.19 (m, 2H), 4.22 - 4.15 (m, 2H), 3.87 (d, J= 2.0 Hz, 2H), 3.65 (q, J= 7.2 Hz, 1H), 1.34 (d, J= 7.2 Hz, 3H), 1.30 - 1.26 (m, 3H).
84.3% To a dried 250 ml three-necked flask was added ethyl 3-oxo-4-phenyl-butanoate (4.00 g, 19.4 mmol), THF (50.0 mL), sodium hydride (931 mg, 23.3 mmol) and the reaction stirred for 0.5 hours at 0° C. A solution of methyl iodide (3.03 g, 21.3) was next added drop-wise. After addition was completed, the reaction mixture was warmed to 20° C. and stirred for two hours at 20° C. The reaction mixture was quenched by addition of water (10.0 mL) at 20° C. and then diluted with ethyl acetate (20.0 mL) and the layers separated. The aqueous layer was next extracted with ethyl acetate (20.0 mL 3). The combined organic layers were washed with brine (30.0 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, Petroleum ether: Ethyl acetate 20:1 to 10:1) to give ethyl 2-methyl-3-oxo-4-phenyl-butanoate (3.60 g, 16.3 mmol, 84.3% yield) as a colorless oil. 1H NMR (400 MHz, CDCl 3) delta=7.38-7.28 (m, 3H), 7.25-7.19 (m, 2H), 4.22-4.15 (m, 2H), 3.87 (d, J=2.0 Hz, 2H), 3.65 (q, J=7.2 Hz, 1H), 1.34 (d, J=7.2 Hz, 3H), 1.30-1.26 (m, 3H).
84.3% With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 2.5h; To a dried 250 ml three-necked flask was added ethyl 3-oxo-4-phenyl-butanoate (4.00 g, 19.4 mmol.), THF (50.0 mL), sodium hydride (931 mg, 23.3 mmol) and the reaction stirred for 0.5 hours at 0C. A solution of methyl iodide (3.03 g, 21.3) was next added drop-wise. After addition was completed, the reaction mixture was warmed to 20 C and stirred for two hours at 20C. The reaction mixture was quenched by addition of water (10.0 mL) at 20 C and then diluted with ethyl acetate (20.0 mL) and the layers separated. The aqueous layer was next extracted with ethyl acetate (20.0 mL c 3). The combined organic layers were washed with brine (30.0 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, Petroleum ether : Ethyl acetate 20: 1 to 10: 1) to give ethyl 2-methyl-3-oxo-4-phenyl-butanoate (3.60 g, 16.3 mmol, 84.3% yield) as a colorless oil. 'H NMR (400 MHz, CDCL) d = 7.38 - 7.28 (m, 3II), 7.25 - 7.19 (m, 2H), 4.22 - 4.15 (m, 2H), 3.87 (d, J = 2.0 Hz, 2H), 3.65 (q, ,7= 7.2 Hz, 1H), 1.34 (d, ,7= 7.2 Hz, 3H), 1.30 - 1.26 (m, 3H).

  • 33
  • [ 718-08-1 ]
  • [ 53114-36-6 ]
YieldReaction ConditionsOperation in experiment
180 mg With ammonium acetate; In ethanol; at 75℃; for 3h; A mixture of ethyl 3-oxo-4-phenylbutanoate (0.200 g, 0.97 mmol) and ammonium acetate (0.374 g, 4.8 mmol) in ethanol (2.0 ml) was heated to 75C. After 3h of stirring the temperature was cooled to 20C and the solvent removed under vacuum. The residue was taken in Et20 and washed with a saturated solution of NaHCO3. The organic phase was separated, dried over anhydrous MgSO4, filtered and the solvent removed under vacuum to yield 180 mg of the title compound. 1 NMR (400 MHz, DMSO-d6) UUppm 1.12 (t, J=7.04 Hz, 3 H) 3.38 (5, 2 H) 3.94 (q, J=7.30 Hz, 2 H) 4.29 (5, 1 H) 7.04 (br. s., 1 H) 7.19 - 7.34 (m,5 H) 7.72 (br. s., 1 H).
  • 34
  • [ 718-08-1 ]
  • [ 1521145-56-1 ]
YieldReaction ConditionsOperation in experiment
100% With iodosylbenzene; hydrogen fluoride; In dichloromethane; water; at 40℃; for 24h; General procedure: To a PFA test tube were added ArIO (1.2 mmol), 55% aq HF soln (0.64 mL, 10 mmol HF), and CH2Cl2 (2 mL). After stirring for 15 min at r.t., a 1,3-dicarbonyl compound 1 (1 mmol) was added and then the mixture was stirred at 40 C for the time given in Table 2. The mixture was poured into H2O (20 mL), neutralized with NaHCO3, and extracted with CH2Cl2 (3 × 6 mL) The combined organic layers were washed with sat. NaCl and dried (anhydrous Na2SO4). After evaporation of the solvent, the product was isolated by column chromatography (silica gel, EtOAc-hexane).
  • 35
  • [ 718-08-1 ]
  • [ 4637-24-5 ]
  • [ 72676-86-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: Appropriate phenylacetyl chloride (1equiv) was added dropwise into a solution of Meldrum's acid (1equiv) and TEA (2.4equiv) in DCM (1M) under ice bath. The reaction mixture was then allowed to warm to room temperature and stirred for 3.5h. The reaction mixture was extracted with a mixture of CH2Cl2 and 1N HCl solution. The organic layer was washed with brine, dried over MgSO4, and concentrated. To the residue was added absolute ethanol (1M), and the reaction mixture was heated at reflux for 2h. The solvent was removed in vacuo, and to the resulting ethyl-4-aryl-3-oxobutanoate ( 27) in xylene (1M) was added DMF-DMA (2.5equiv). The resulting mixture was heated at reflux for 4h and then concentrated in vacuo. To the solution of residue in MeOH (1M) was added ammonium acetate (5equiv), and the resultant mixture was heated at reflux for 4h. The crude ethyl ester of appropriate 29 was saponified by 10% (w/v) NaOH (10mL) in MeOH (20mL) at reflux for 2.5h. The mixture was then adjusted to pH 1 by titrating with 3N HCl. The precipitate was collected by filtration, washed with MeOH, water, and diethyl ether, and dried to give appropriate analogs of 29.
  • 36
  • [ 718-08-1 ]
  • [ 104-87-0 ]
  • C18H15NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With hydroxylamine hydrochloride; boric acid; In water; at 20℃; for 1.25h;Green chemistry; General procedure for preparation of 4H-isoxazole-5(4H)-ones (4a-x)A mixture of equimolar quantities of hydroxylamine hydrochloride 2 (0.07 g,1 mmol) and b-ketoester 3 (0.130 g, 1 mmol) were stirred in 5 mL of water for5 min. Then, aryl aldehyde 1a-p (1 mmol) and 10 mol % of boric acid was addedand the reaction mixture was stirred at room temperature for the indicated timeshown in Table 2 (below). The solid product formed was isolated by simplefiltration and washed with water (5 mL). The products obtained were shown to bepure by TLC and spectral techniques. The filtrate was evaporated to remove water,leaving the catalyst. The same catalyst was employed to synthesize furtherderivatives. If necessary, further purification was performed by recrystallizationfrom suitable solvents such as EtOH to give the desired compounds in high yields.The products are known and their identity was confirmed by comparison of theirphysical and spectroscopic data with those available in recent papers [31-38].
  • 37
  • [ 718-08-1 ]
  • [ 100-10-7 ]
  • C19H18N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With hydroxylamine hydrochloride; boric acid; In water; at 20℃; for 1.58333h;Green chemistry; General procedure for preparation of 4H-isoxazole-5(4H)-ones (4a-x)A mixture of equimolar quantities of hydroxylamine hydrochloride 2 (0.07 g,1 mmol) and b-ketoester 3 (0.130 g, 1 mmol) were stirred in 5 mL of water for5 min. Then, aryl aldehyde 1a-p (1 mmol) and 10 mol % of boric acid was addedand the reaction mixture was stirred at room temperature for the indicated timeshown in Table 2 (below). The solid product formed was isolated by simplefiltration and washed with water (5 mL). The products obtained were shown to bepure by TLC and spectral techniques. The filtrate was evaporated to remove water,leaving the catalyst. The same catalyst was employed to synthesize furtherderivatives. If necessary, further purification was performed by recrystallizationfrom suitable solvents such as EtOH to give the desired compounds in high yields.The products are known and their identity was confirmed by comparison of theirphysical and spectroscopic data with those available in recent papers [31-38].
  • 38
  • [ 718-08-1 ]
  • [ 123-08-0 ]
  • C17H13NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With hydroxylamine hydrochloride; boric acid; In water; at 20℃; for 1.5h;Green chemistry; General procedure for preparation of 4H-isoxazole-5(4H)-ones (4a-x)A mixture of equimolar quantities of hydroxylamine hydrochloride 2 (0.07 g,1 mmol) and b-ketoester 3 (0.130 g, 1 mmol) were stirred in 5 mL of water for5 min. Then, aryl aldehyde 1a-p (1 mmol) and 10 mol % of boric acid was addedand the reaction mixture was stirred at room temperature for the indicated timeshown in Table 2 (below). The solid product formed was isolated by simplefiltration and washed with water (5 mL). The products obtained were shown to bepure by TLC and spectral techniques. The filtrate was evaporated to remove water,leaving the catalyst. The same catalyst was employed to synthesize furtherderivatives. If necessary, further purification was performed by recrystallizationfrom suitable solvents such as EtOH to give the desired compounds in high yields.The products are known and their identity was confirmed by comparison of theirphysical and spectroscopic data with those available in recent papers [31-38].
  • 39
  • [ 718-08-1 ]
  • [ 100-52-7 ]
  • C17H13NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With hydroxylamine hydrochloride; boric acid; In water; at 20℃; for 1.66667h;Green chemistry; General procedure: General procedure for preparation of 4H-isoxazole-5(4H)-ones (4a-x)A mixture of equimolar quantities of hydroxylamine hydrochloride 2 (0.07 g,1 mmol) and b-ketoester 3 (0.130 g, 1 mmol) were stirred in 5 mL of water for5 min. Then, aryl aldehyde 1a-p (1 mmol) and 10 mol % of boric acid was addedand the reaction mixture was stirred at room temperature for the indicated timeshown in Table 2 (below). The solid product formed was isolated by simplefiltration and washed with water (5 mL). The products obtained were shown to bepure by TLC and spectral techniques. The filtrate was evaporated to remove water,leaving the catalyst. The same catalyst was employed to synthesize furtherderivatives. If necessary, further purification was performed by recrystallizationfrom suitable solvents such as EtOH to give the desired compounds in high yields.The products are known and their identity was confirmed by comparison of theirphysical and spectroscopic data with those available in recent papers [31-38].
  • 40
  • [ 718-08-1 ]
  • [ 123-11-5 ]
  • C18H15NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With hydroxylamine hydrochloride; boric acid; In water; at 20℃; for 1.16667h;Green chemistry; General procedure for preparation of 4H-isoxazole-5(4H)-ones (4a-x)A mixture of equimolar quantities of hydroxylamine hydrochloride 2 (0.07 g,1 mmol) and b-ketoester 3 (0.130 g, 1 mmol) were stirred in 5 mL of water for5 min. Then, aryl aldehyde 1a-p (1 mmol) and 10 mol % of boric acid was addedand the reaction mixture was stirred at room temperature for the indicated timeshown in Table 2 (below). The solid product formed was isolated by simplefiltration and washed with water (5 mL). The products obtained were shown to bepure by TLC and spectral techniques. The filtrate was evaporated to remove water,leaving the catalyst. The same catalyst was employed to synthesize furtherderivatives. If necessary, further purification was performed by recrystallizationfrom suitable solvents such as EtOH to give the desired compounds in high yields.The products are known and their identity was confirmed by comparison of theirphysical and spectroscopic data with those available in recent papers [31-38].
  • 41
  • [ 91962-64-0 ]
  • [ 718-08-1 ]
YieldReaction ConditionsOperation in experiment
58% With Oxone; In water; N,N-dimethyl-formamide; at 80℃;Green chemistry; General procedure: To a solution of the oxone (0.5 equiv) in DMF(2 mL) was added allene (0.5 mmol, 1.0 equiv), and then H2O(5.0 equiv) was added dropwise to the system. The reaction mixturewas transferred to an 80 C oil bath and conducted at the indicated temperature for the stated time. After the reaction wascompleted and cooled to room temperature, 5 mL water was addedand extracted with EtOAc (8 mL 3) to remove most of DMF. Theorganic phases were collected, washed with saturated brine toremove the residual DMF, dried over anhydrous Na2SO4, andconcentrated under reduced pressure. Purification by flashchromatography on silica gel (petroleum/ethyl acetate = 50:1 to20:1) afforded the corresponding product.
  • 42
  • [ 718-08-1 ]
  • [ 26421-44-3 ]
  • ethyl (2Z,4E)-5-(2,5-dimethylthiophen-3-yl)-2-[(2,5-dimethylthiophen-3-yl)methylene]-3-oxo-4-phenylpent-4-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With piperidine; acetic acid; In benzene;Reflux; Dean-Stark; General procedure: A solution of keto ester 5a-e (2 mmol) in anhydrous benzene (10 ml) was treated with the corresponding aldehyde (4 mmol), piperidine (0.04 ml, 0.4 mmol), and acetic acid (0.11 ml, 2 mmol), and refluxed for 1-5 h in a flask with Dean-Stark trap. After the reaction was finished (control by TLC), the reaction mixture was evaporated under vacuum and purified by column chromatography.
  • 43
  • [ 718-08-1 ]
  • [ 94-41-7 ]
  • ethyl 3'-oxo-5'-phenyl-3',4',5',6'-tetrahydro[1,1':2',1''-terphenyl]-4'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium hydroxide; In ethanol; at 20℃; for 24h; General procedure: KOH (0.6 mmol) was added to a solution of the keto ester 5 (1.23mmol) and the chalcone 3 (1.23 mmol) in EtOH (4 mL). The resultingsuspension was stirred for 24 h at r.t. After the completion of the reaction(TLC control) the precipitated product formed was collected byfiltration, washed with H2O (50 mL) and cold EtOH (5 mL), and driedunder vacuum. Additional quantities of the product were obtained asfollowing: filtrate was poured into H2O (50 mL), extracted with EtOAc(3 × 30 mL), washed with brine (70 mL), dried (MgSO4), and evaporatedunder vacuum. The residue was purified by column chromatography(silica gel, PE-EtOAc, 6:1). Ethyl 3?-Oxo-5?-phenyl-3?,4?,5?,6?-tetrahydro-[1,1?:2?,1??-terphenyl]-4?-carboxylate (6a)Colorless crystals; yield: 341 mg (70%); mp 160-161 C.IR (KBr): 3024, 2993, 1741, 1664, 1256, 1032, 697 cm-1.1H NMR (300 MHz, CDCl3): delta = 1.10 (t, J = 7.1 Hz, 3 H, CH3), 3.05-3.19(m, 2 H, CH2), 3.92-4.16 (m, 4 H, CH+CH+CH2), 6.91-7.43 (m, 15 H,Harom).13C NMR (75 MHz, CDCl3): delta = 14.0, 40.4, 43.4, 60.1, 61.0, 127.1, 127.2(2 C), 127.4, 127.6 (2 C), 128.0 (2 C), 128.2 (3 C), 128.8 (2 C), 131.0 (2C), 134.7, 136.8, 139.9, 141.1, 156.6, 169.3, 193.2. MS (EI, 70 eV): m/z (%) = 396 (60) [M]+, 323 (100) [M - CO2Et]+.HRMS (ESI): m/z [M + H]+ calcd for C27H24O3: 397.1798; found:397.1782.
  • 44
  • [ 718-08-1 ]
  • 1-(2,5-dimethylthiophen-3-yl)-3-phenylprop-2-en-1-one [ No CAS ]
  • ethyl 5'-(2,5-dimethyl-3-thienyl)-3'-oxo-1',2',3',6'-tetrahydro[1,1':4',1''-terphenyl]-2'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With potassium hydroxide; In ethanol; at 20℃; for 24h; General procedure: KOH (0.6 mmol) was added to a solution of the keto ester 5 (1.23mmol) and the chalcone 3 (1.23 mmol) in EtOH (4 mL). The resultingsuspension was stirred for 24 h at r.t. After the completion of the reaction(TLC control) the precipitated product formed was collected byfiltration, washed with H2O (50 mL) and cold EtOH (5 mL), and driedunder vacuum. Additional quantities of the product were obtained asfollowing: filtrate was poured into H2O (50 mL), extracted with EtOAc(3 × 30 mL), washed with brine (70 mL), dried (MgSO4), and evaporatedunder vacuum. The residue was purified by column chromatography(silica gel, PE-EtOAc, 6:1).
  • 45
  • [ 718-08-1 ]
  • C19H15NO2 [ No CAS ]
  • ethyl 5'-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-3'-oxo-1',2',3',6'-tetrahydro[1,1':4',1''-terphenyl]-2'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium hydroxide; In ethanol; for 24h;Reflux; General procedure: KOH (0.6 mmol) was added to a solution of the keto ester 5 (1.23mmol) and the chalcone 3 (1.23 mmol) in EtOH (4 mL). The resultingsuspension was stirred for 24 h at r.t. After the completion of the reaction(TLC control) the precipitated product formed was collected byfiltration, washed with H2O (50 mL) and cold EtOH (5 mL), and driedunder vacuum. Additional quantities of the product were obtained asfollowing: filtrate was poured into H2O (50 mL), extracted with EtOAc(3 × 30 mL), washed with brine (70 mL), dried (MgSO4), and evaporatedunder vacuum. The residue was purified by column chromatography(silica gel, PE-EtOAc, 6:1).
  • 46
  • [ 718-08-1 ]
  • [ 1608-51-1 ]
  • ethyl 5'-(4-fluorophenyl)-3'-oxo-3',4',5',6'-tetrahydro[1,1':2',1''-terphenyl]-4'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium hydroxide; In ethanol; at 20℃; for 24h; General procedure: KOH (0.6 mmol) was added to a solution of the keto ester 5 (1.23mmol) and the chalcone 3 (1.23 mmol) in EtOH (4 mL). The resultingsuspension was stirred for 24 h at r.t. After the completion of the reaction(TLC control) the precipitated product formed was collected byfiltration, washed with H2O (50 mL) and cold EtOH (5 mL), and driedunder vacuum. Additional quantities of the product were obtained asfollowing: filtrate was poured into H2O (50 mL), extracted with EtOAc(3 × 30 mL), washed with brine (70 mL), dried (MgSO4), and evaporatedunder vacuum. The residue was purified by column chromatography(silica gel, PE-EtOAc, 6:1).
  • 47
  • [ 718-08-1 ]
  • [ 956-04-7 ]
  • ethyl 5'-(4-chlorophenyl)-3'-oxo-3',4',5',6'-tetrahydro[1,1':2',1'-terphenyl]-4'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium hydroxide; In ethanol; at 20℃; for 24h; General procedure: KOH (0.6 mmol) was added to a solution of the keto ester 5 (1.23mmol) and the chalcone 3 (1.23 mmol) in EtOH (4 mL). The resultingsuspension was stirred for 24 h at r.t. After the completion of the reaction(TLC control) the precipitated product formed was collected byfiltration, washed with H2O (50 mL) and cold EtOH (5 mL), and driedunder vacuum. Additional quantities of the product were obtained asfollowing: filtrate was poured into H2O (50 mL), extracted with EtOAc(3 × 30 mL), washed with brine (70 mL), dried (MgSO4), and evaporatedunder vacuum. The residue was purified by column chromatography(silica gel, PE-EtOAc, 6:1).
  • 48
  • [ 718-08-1 ]
  • [ 95793-44-5 ]
  • ethyl 5'-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-3'-oxo1',2',3',6'-tetrahydro-[1,1':4',1'-terphenyl]-2'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium hydroxide; In ethanol; at 20℃; for 24h; General procedure: KOH (0.6 mmol) was added to a solution of the keto ester 5 (1.23mmol) and the chalcone 3 (1.23 mmol) in EtOH (4 mL). The resultingsuspension was stirred for 24 h at r.t. After the completion of the reaction(TLC control) the precipitated product formed was collected byfiltration, washed with H2O (50 mL) and cold EtOH (5 mL), and driedunder vacuum. Additional quantities of the product were obtained asfollowing: filtrate was poured into H2O (50 mL), extracted with EtOAc(3 × 30 mL), washed with brine (70 mL), dried (MgSO4), and evaporatedunder vacuum. The residue was purified by column chromatography(silica gel, PE-EtOAc, 6:1).
  • 49
  • [ 718-08-1 ]
  • [ 61-82-5 ]
  • [ 92368-39-3 ]
YieldReaction ConditionsOperation in experiment
55% With acetic acid; at 115℃; for 16h;Inert atmosphere; Ethyl 3-oxo-4-phenylbutanoate (1.5 g, 7.2 mmol) was taken in AcOH (8 mL) in a 50 mL round bottom flask under N2. To it was added 1H-1,2,4-triazol-5-amine (733 mg, 8.7 mmol). The reaction mixture was heated at 115 C for 16 h. The reaction mixture was then evaporated to dryness using toluene as an azeotropic solvent and triturated with diethyl ether. This was finally dried under high vacuum which afforded 4n as a white solid (910 mg, 55%). This was then used in the next step without any further purification.
  • 50
  • [ 718-08-1 ]
  • [ 106-95-6 ]
  • [ 634603-35-3 ]
  • 51
  • [ 718-08-1 ]
  • 3-aminobenzenecrotonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.71% With ammonium hydroxide; at 30℃; (1) Add 34.5% to a 250 mL four-neck round bottom flask equipped with mechanical stirring(mass fraction) Ammonia (100g, 2.05mol), Formula (I-4)Ethyl 3-oxophenylbutyrate (20.6 g, 0.10 mol),After reacting under normal pressure at 30C, the reaction was completed after liquid chromatography.The reaction solution is filtered and the filtrate can be applied directly to the next batch.The resulting filter cake was washed with fresh water for 2-3 times.Place the drying oven at 50-60C,In the formula (II-4), 14.38 g of 3-aminobenzenecrotonamide is shown,The purity was 98.4% by liquid chromatography and the yield was 81.71%.
  • 52
  • [ 718-08-1 ]
  • [ 34457-01-7 ]
  • ethyl (4S,5R)-3-oxo-4-phenyl-5-(o-tolyl)hexanoate [ No CAS ]
  • 53
  • [ 4360-63-8 ]
  • [ 718-08-1 ]
  • ethyl 5-(1,3-dioxolane-2-yl)-3-oxo-4-phenylvalerate [ No CAS ]
YieldReaction ConditionsOperation in experiment
870 mg Ethyl 3-oxo-4-phenylbutyrate (1.03 g, according to the European Journal of Medicinal The method described in Chemistry, 2014, Vol 84, 312-334] is dissolved in anhydrous tetrahydrofuran (20 ml), cooled in an ice-water bath, and slowly added in small portions with 60% purity of mineral oil and sodium hydride under nitrogen flow The solid was mixed (200 mg) and stirred for 0.5 h; then hexamethylphosphoramide (2.7 g) and a 1.6 M solution of n-butyllithium in hexane (3.13 ml) were added sequentially;2-Bromomethyl-1,3-dioxolane (840 mg) was then added. The reaction was stirred at room temperature overnight. The reaction solution was carefully poured into saturated aqueous ammonium chloride, and then extracted with ethyl acetate; the ethyl acetate layer was separated, and then washed twice with dilute aqueous sodium chloride solution; the ethyl acetate phase was dried over anhydrous sodium sulfate; The desiccant was removed by filtration and the filtrate was spin-dried on a rotary evaporator; the residue was purified by column chromatography to give the product 1b (870 mg).
  • 54
  • [ 718-08-1 ]
  • [ 7357-70-2 ]
  • 4-benzyl-2-mercapto-6-oxo-1,6-dihydropyridine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
891 mg With potassium tert-butylate; In N,N-dimethyl-formamide; at 20 - 90℃; for 4h;Inert atmosphere; To a solution of ethyl3-oxo-4-phenylbutanoate (2 g, 10.4 mmol) and 2-cyanoethanethioamide (1.56 g, 15.6 mmol) in DMF (60 mL) was added t-BuOK (5.8 g, 52mmol) at room temperature. The reaction was heated at 90 oc for 4 h under N2. TLC (50%PE/50% EtOAc, silica gel plate) showed complete consumption of the starting material afterthis time. The mixture was concentrated in vacuo. The residue was purified via reverse phasecolumn chromatography (MeOH/H20 = 5%-80%) to give the desired compound (891 mg) asa brown solid. LC-MS (ESI+): m/z 243.0 (M+Ht.
  • 55
  • [ 718-08-1 ]
  • [ 4637-24-5 ]
  • C18H24N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% at 110℃; for 3h; The above liquid was added into DMF-DMA and reacted for 3 h with stirring at 110 C. After the reaction was completed, the resultant was concentrated and stirred in EA to give a white solid, yield 81%. 1H NMR (DMSO, 300 MHz): delta 7.37-7.14 (m, 5H), 7.06 (s, 1H), 7.04 (s, 1H), 4.07-3.87 (m, 2H), 2.92 (s, 6H), 2.65 (s, 6H), 1.13 (t, J=7.1 Hz, 3H).
  • 56
  • [ 718-08-1 ]
  • [ 1147550-11-5 ]
  • ethyl (E)-3-amino-4-phenyl-2-thiocyanatobut-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With fluorescein; In acetonitrile; at 20℃; for 6h;Irradiation; Under the room temperature condition, 3 - oxygen -4 - phenyl - butyric acid ethyl ester (103 mg, 0.5 mmol), thiocyanate amine (114, 2 mg, 1.5 mmol), fluorescein (3.3 mg, 2 muM %) is added to 10 ml reaction tube, then adding solvent acetonitrile 2 ml, in 3.0 W under the irradiation of blue LED, in the air reaction 6 hours, detected by TLC. After the completion of the reaction, the reaction mixture is concentrated in vacuo, the remaining crude by column chromatography to obtain 4 - phenyl -3 amino -2 - cyano group butenate white solid 116.6 mg, yield 89%.
  • 57
  • [ 718-08-1 ]
  • C8H15IO2 [ No CAS ]
  • C16H18O4 [ No CAS ]
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