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Chemical Structure| 60456-77-1 Chemical Structure| 60456-77-1

Structure of 60456-77-1

Chemical Structure| 60456-77-1

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Product Details of [ 60456-77-1 ]

CAS No. :60456-77-1
Formula : C11H8O2
M.W : 172.18
SMILES Code : O=CC1=CC=C(C2=CC=CO2)C=C1
MDL No. :MFCD03030050
InChI Key :WBUXKMOCVYRVES-UHFFFAOYSA-N
Pubchem ID :2772295

Safety of [ 60456-77-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312+P330-P501

Application In Synthesis of [ 60456-77-1 ]

* 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 [ 60456-77-1 ]

[ 60456-77-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 110-00-9 ]
  • [ 1122-91-4 ]
  • [ 60456-77-1 ]
  • 2
  • [ 60456-77-1 ]
  • [ 2483-57-0 ]
  • [ 61973-98-6 ]
  • 3
  • [ 60456-77-1 ]
  • [ 17920-85-3 ]
  • 1,2-Bis-(4-furan-2-yl-phenyl)-ethane-1,2-dione [ No CAS ]
  • 4
  • [ 196952-88-2 ]
  • [ 60456-77-1 ]
  • C22H16O4 [ No CAS ]
  • 5
  • [ 60456-77-1 ]
  • [ 255065-87-3 ]
  • (2,4,5-Triphenyl-imidazol-1-yl)-acetic acid [1-(4-furan-2-yl-phenyl)-meth-(E)-ylidene]-hydrazide [ No CAS ]
  • 6
  • [ 60456-77-1 ]
  • [ 255065-89-5 ]
  • [2-(4-Fluoro-phenyl)-4,5-diphenyl-imidazol-1-yl]-acetic acid [1-(4-furan-2-yl-phenyl)-meth-(E)-ylidene]-hydrazide [ No CAS ]
  • 7
  • [ 60456-77-1 ]
  • [ 255065-88-4 ]
  • [2-(4-Dimethylamino-phenyl)-4,5-diphenyl-imidazol-1-yl]-acetic acid [1-(4-furan-2-yl-phenyl)-meth-(E)-ylidene]-hydrazide [ No CAS ]
  • 8
  • [ 110-00-9 ]
  • [ 87199-17-5 ]
  • [ 60456-77-1 ]
  • 9
  • [ 60456-77-1 ]
  • 2-[2-(4-fluoro-phenyl)-4,5-diphenyl-imidazol-1-ylmethyl]-5-(4-furan-2-yl-phenyl)-[1,3,4]oxadiazole [ No CAS ]
  • 10
  • [ 60456-77-1 ]
  • (4-{1-[5-(4-furan-2-yl-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-4,5-diphenyl-1<i>H</i>-imidazol-2-yl}-phenyl)-dimethyl-amine [ No CAS ]
  • 11
  • [ 623-27-8 ]
  • [ 60456-77-1 ]
  • 12
  • 4-(1-Hydroxy-buta-2,3-dienyl)-benzaldehyde [ No CAS ]
  • [ 60456-77-1 ]
  • 13
  • [ 166328-14-9 ]
  • [ 104-88-1 ]
  • [ 60456-77-1 ]
  • 14
  • [ 166328-14-9 ]
  • [ 1122-91-4 ]
  • [ 60456-77-1 ]
  • 15
  • [ 13331-23-2 ]
  • [ 1122-91-4 ]
  • [ 60456-77-1 ]
YieldReaction ConditionsOperation in experiment
95% With tetrabutylammomium bromide; potassium carbonate; In methanol; water; at 80℃; for 0.25h;Reflux; General procedure: A mixture of hetarylboronic acid 4a-d(1.2 mmol), aryl(hetaryl) bromide 5a-h or hetaryl chloride7a,b (1 mmol), Bu4NBr (3 mg, 1 mol %, for water-insolublearyl(hetaryl) halides 5b-g and 7a,b), and K2CO3 (346 mg,2.5 mmol) in 2 (5 ml) was heated to 80 and treated byadding 0.1-1 mol % of Pd-Ni(Co)-B-L (an aliquot of0.1 M solution of bimetallic catalyst in MeOH-H2Omixture). The reactor was fitted with a reflux condenserand placed in a hot silicone oil bath (150). The reactionmixture was vigorously stirred at reflux until completeconversion of the starting materials was achieved. Thereaction progress was controlled by TLC method (eluenthexane-Et2O, 3:1). The amount of catalyst, reactionduration and yields of the target compounds 6a-k are listedin Table 4. In the case of the activated aryl bromides5a,b,d,f, the reaction was highly exothermic, therefore aneffective reflux condenser was essential for scaling up thissynthesis.After the reaction was complete, the mixture was dilutedwith H2O (10 ml), heated to 80C, and filtered while hotthrough a Whatman autovial syringeless filter (pore size0.45 μm). The filtrate was diluted with 10-15 vol % ofEtOH, heated to ~50C, stirred, and slowly acidified with5% HCl to pH 2-3. The resulting precipitate was easy tofilter, and analytically pure products 6a,h,k were obtainedwithout chromatographic purification. In the case of thewater-insoluble heterobiaryls 6b-g,i,j, the reaction mixturewas diluted with saturated solution of NaCl (10 ml) andextracted with Et2O or EtOAc (3×5 ml). The obtainedextract was dried over anhydrous Na2SO4, filtered througha silica gel layer, and the solvent was evaporated at reducedpressure. The residues in all cases were >99% pureproducts (according to the results of elemental analysis).Analytically pure samples were obtained by recrystallizationof heterobiaryls 6a-k from a minimal amount ofaqueous EtOH (10-20% 2) or by converting amines intothe respective hydrochlorides. The residual metal content inthe isolated heterobiaryls 6a-k did not exceed 1 ppmaccording to the results of atomic absorption spectrometry.
84% In a 100 mL three-necked flask, 2-furanboronic acid (0.559 g, 5 mmol), 4-bromobenzaldehyde (0.925 g, 5 mmol), K2CO3 (0.696 g, 1 N) and N,N-dimethylformamide (10 mL) ). First, stir for 30 minutes under N2 atmosphere.The air remaining in the reactor was removed, and then palladium acetate (9 mg), triphenylphosphine (60 mg) was added. The reaction was carried out at 90 C for 6 hours. After the reaction was completed, it was cooled to room temperature, dissolved in dichloromethane and washed sequentially with water (50 ml). Finally, it was purified by column chromatography, and the product was dark green oil (0.65 g).The yield was 84%.
47% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In ethanol; water; toluene;Reflux; General procedure: Tetrakis(triphenylphosphine)palladium(0) (0.0168 mmol) was added to a solution of 4-bromobenzaldehyde (50, 5.6 mmol) in ethanol-toluene (40 mL, 1:1). After 15 min, the appropriate boronic acid 51b-m (6.75 mmol) was added, followed by sodium hydrogen carbonate (22.4 mmol) and water (11 mL). The resulting mixture was heated under reflux for 9-15 hours. After cooling, the reaction mixture was filtered through Celite, the organic phase was separated, washed with brine (2x20 mL), dried and the solvent evaporated in vacuo. The residue thus obtained was purified by flash-chromatography. Elution by light petroleum-ethyl acetate mixtures afforded the desired compounds.
  • 16
  • [ 60456-77-1 ]
  • [ 91331-68-9 ]
  • C22H19N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene;Reflux; General procedure: The appropriate 1-substituted-3-methyl-5-aminopyrazole 46 (1.0 mmol) and the aldehyde 47 (1.0 mmol) were heated under reflux in toluene (50 mL) for 7-9 hours; during this period produced water was removed with the aid of a Dean-Stark apparatus. The reaction mixture was cooled, 2-mercaptopropanoic acid (1.0 mmol) was added and the mixture heated again at reflux for 12 hours. The solvent was removed in vacuo and the residue submitted to medium pressure liquid chromatography. Elution by light petroleum-ethyl acetate mixtures afforded the desired compounds.
  • 17
  • [ 60456-77-1 ]
  • [ 91331-68-9 ]
  • 4-[4-(2-furanyl)phenyl]-3,6-dimethyl-1-(2-methylphenyl)-4,8-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-7-one [ No CAS ]
  • 4-[4-(2-furanyl)phenyl]-3,6-dimethyl-1-(2-methylphenyl)-4,8-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-7-one [ No CAS ]
  • 18
  • [ 60456-77-1 ]
  • 14-dehydroxy-11,12-didehydroandrographolide [ No CAS ]
  • C25H30O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With sulfuric acid; In tetrahydrofuran;Reflux; General procedure: Compound 4 was prepared according to theliterature protocol ( Bioorg. Med. Chem. 2007, 15, 4247).Compound2 (100 mg, 0.30 mmol) and 4-nitro-benzaldehyde (68 mg, 0.45 mmol) in THF were refluxed for 2~4h in thepresence of H2SO4. The reaction mixture was concentratedunder reduced pressure and diluted with CH2Cl2. The CH2Cl2phase was washed with aq Na2CO3, brine and watersuccessively, then was dried overanhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified bysilica gel column chromatography (gradient elution, EtOAc/PE = 1:10 to 1:3) to afford 4a as white powder (112 mg, 0.24 mmol,80%).Compounds4b-f were prepared with similar protocols.
  • 19
  • [ 60456-77-1 ]
  • C24H24N2O2 [ No CAS ]
  • 20
  • [ 60456-77-1 ]
  • [ 107-15-3 ]
  • C24H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 0.666667h;Heating; General procedure: General procedure for synthesis of BC-1260. <strong>[60456-77-1]4-(2-furyl)benzaldehyde</strong> (0.004 mol, 0.69 g) were added to a solution of ethylenediamine (0.002 mol, -140 ul) in anhydrous ethanol (20 ml). The resulting solution was heated and stirred for 40 min until the precipitation of the relevant Schiff base. The Schiff bases were filtered off, and washed with cold ethanol. The Schiff base was then added to 15 ml absolute methanol. A 10% solution of sodium borohydride (0.01 mol) was dissolved in absolute methanol and added to the Schiff base. When the dropwise addition of sodium borohydride was complete, the reaction solution was refluxed for an additional 15 min. Solvent was then removed through rotary evaporation and 20 ml cold water was added to liberate the secondary amine. The precipitation of BC-1260 were collected, washed with water and dried, followed by recrystallization from ethyl acetate.
  • 21
  • [ 60456-77-1 ]
  • [ 105-56-6 ]
  • ethyl 2-amino-4-(furan-2-yl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate [ No CAS ]
  • 22
  • [ 60456-77-1 ]
  • [ 105-56-6 ]
  • [ 773083-33-3 ]
YieldReaction ConditionsOperation in experiment
With dmap; In ethanol; water; at 20℃; for 0.5h; General procedure: A mixture of 4-nitrobenzaldehyde (1 mmol) and ethyl cyanoacetate (1 mmol) in H2O/EtOH (1:1) (5 mL) was treated with DMAP (10 mol%) at room temperature. After the consumption of starting aldehyde as indicated by TLC analysis (30 min), 4-hydroxy-1-methyl-2(1H)-quinolinone (1 mmol) was added to the reaction mixture and the mixture was heated to reflux condition for 2 h. After the completion of the reaction, the reaction mixture was brought to room temperature and the solid precipitate was collected by filtration. The desired product 4a was obtained as a yellow powder.
  • 23
  • [ 60456-77-1 ]
  • [ 551-93-9 ]
  • [ 1417196-27-0 ]
  • (R)-2-(furan-2-yl)-2,3-dihydroquinolin-4(1H)-one [ No CAS ]
  • 24
  • [ 17920-85-3 ]
  • [ 60456-77-1 ]
  • 25
  • [ 60456-77-1 ]
  • [ 107-15-3 ]
  • C24H24N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Compound 013: <strong>[60456-77-1]4-(2-furyl)benzaldehyde</strong> (0.004 mol, 0.69 g) was added to a solution of ethylenediamine (0.002 mol, -140 ul) in anhydrous ethanol (20 ml). The resulting solution was heated and stirred for 40 min until the precipitation of the relevant Schiff base. The Schiff bases were filtered off, and washed with cold ethanol. The Schiff base was then added to 15 ml absolute methanol. A 10% solution of sodium borohydride (0.01 mol) was dissolved in absolute methanol and added to the Schiff base. When the dropwise addition of sodium borohydride was complete, the reaction solution was refluxed for an additional 15 min. Solvent was then removed through rotary evaporation and 20 ml cold water was added to liberate the secondary amine. The precipitation of Compound 013 were collected, washed with water and dried, followed by recrystallization from ethyl acetate.
  • 26
  • [ 60456-77-1 ]
  • methyl 4-((5-(piperidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl)benzoate [ No CAS ]
  • methyl 4-((5-(1-(4-(furan-2-yl)benzyl)piperidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.4% With sodium tris(acetoxy)borohydride; In dichloromethane; at 20℃; for 3h; The compound of formula 6-3 (methyl4-((5-(piperidin-4-yl)- 1 H-pyrrolo[2,3-b]pyridin- 1 -yl)methyl)benzoate) (ft 100 g, 0.286 mmol), <strong>[60456-77-1]4-(furan-2-yl)benzaldehyde</strong> (0.074 g, 0.429 mmol), and sodium triacetoxyborohydride (0.09 1 g, 0.429 mmol) were dissolved in methylene chloride (3 mL) at room temperature, and the solution was stirred at the same temperature for 3 hours. Water was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was purified by column chromatography (SiO 2, 12 g cartridge; methanol I methylene chloride = from 0% to 10%) to afford the desired compound of formula 12-2 (0.095 g, 65.4%) as a yellow liquid.
  • 27
  • [ 60456-77-1 ]
  • methyl 4-(((2S,6R)-2,6-dimethylpiperazin-1-yl)methyl)benzoate [ No CAS ]
  • methyl 4-(((2S,6R)-4-(4-(furan-2-yl)benzyl)-2,6-dimethylpiperazin-1-yl)methyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.2% [13751 Step 1: Synthesis of methyl4-(((25 .6R’)-4-(4-(furan-2-vflbenzvl’)-2.6-dimethvlpiperazin- 1 -yl’)methyflbenzoate [13761 Methyl 4-(((25 ,6R)-2,6-dimethylpiperazin- 1 -yl)methyl)benzoate (formula 13-2,0.100 g, 0.381 mmol), <strong>[60456-77-1]4-(furan-2-yl)benzaldehyde</strong> (0.066 g, 0.381 mmol) and acetic acid (0.011 mL, 0.38 1 mmol) were dissolved in 1,2-ethylene chloride (4 mL), and stirred at room temperature for 2 hours, and then Na(CN)BH3 (0.024 g, 0.381 mmol) was added thereto, followed by stirring at the same temperature for 17 hours. Then, water was added to the reaction mixture, followed by extraction with methylene chloride. The extract was passed through a plastic filter to remove solid residue and an aqueous layer, and the organic layer was concentrated under reduced pressure. The concentrate was purified by column chromatography (silicon dioxide, 4 g cartridge; ethyl acetate/hexane = from 0 % to 20 %) and concentrated to afford the desired compound (0.053 g, 33.2 %) as a pale yellow oil.
  • 28
  • [ 60456-77-1 ]
  • methyl 4-(((2S,6R)-2,6-dimethylpiperazin-1-yl)methyl)benzoate [ No CAS ]
  • 4-(((2S,6R)-4-(4-(furan-2-yl)benzyl)-2,6-dimethylpiperazin-1-yl)methyl)-N-hydroxybenzamide [ No CAS ]
  • 29
  • [ 13138-21-1 ]
  • [ 60456-77-1 ]
  • [ 31909-58-7 ]
  • 30
  • [ 60456-77-1 ]
  • [ 98-86-2 ]
  • C19H14O2 [ No CAS ]
  • 31
  • [ 60456-77-1 ]
  • [ 98-86-2 ]
  • C29H23NO2 [ No CAS ]
  • 32
  • [ 675-10-5 ]
  • [ 60456-77-1 ]
  • [ 109-77-3 ]
  • C20H14N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With nano cellulose-OSO3H; In ethanol; for 0.2h;Reflux; Green chemistry; General procedure: A mixture of aromatic aldehyde (1 m mol), malononitrile (1.2 mmol), and 4-hydroxy-6-methyl-2H-pyran-2-one (1 mmol) in 5 mL of EtOH was refluxed for the appropriate time in the presence of nano-cellulose-OSO3H (0.008 g). After completion of reaction, as indicated by TLC (n-hexane:ethyl acetate 3:1), the reaction mixture was filtered to remove the catalyst. After evaporation of the solvent, the crude product was recrystallized from hot ethanol to obtain the pure compound. Then, NaOH solution (5 mL,0.1 M) was added to the recovered nano-cellulose-OSO3H(100 mg) in an Erlenmeyer flask. This solution was stirred for 20 min. The excess amount of base was neutralized by adding HCl solution (0.05 M, 1.2 mL) to the equivalence point of titration.
  • 33
  • [ 60456-77-1 ]
  • [ 109-77-3 ]
  • [ 28004-62-8 ]
  • 5-amino-2-(4-chlorophenyl)-7-(furan-2-yl)-7H-(1,3,4)thiadiazolo(3,2-a)pyrimidine-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydroxide; In ethanol; at 80℃; for 1.3h;Sonication; Green chemistry; General procedure: A 25 mL a beaker was charged with a mixture of an 5-(4-chlorophenyl)-1,3,4-thiadiazol-2 amine (0.01 mol) (1), malononitrile (0.01 mol) (2), suitable aldehyde (0.01 mol) (3) inethanol (10-12 mL) and the catalyst NaOH (20% mmol) and the reaction mixture was kept insidean Ultrasonicator acoustic chamber at 80 C at 20%. After completion of the reaction (monitored byTLC), the mixture was poured into ice cold water. The product obtained, was filtered and dried. Thecorresponding product was obtained in high purity after recrystallization of the crude product fromethanol. The authenticity of compounds was established by 1H-NMR, 13C-NMR, IR and HRMS.
  • 34
  • [ 60456-77-1 ]
  • [ 103441-58-3 ]
  • C20H14O2 [ No CAS ]
  • 35
  • [ 60456-77-1 ]
  • [ 103441-58-3 ]
  • C20H16O3 [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 60456-77-1 ]

Aryls

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Related Parent Nucleus of
[ 60456-77-1 ]

Furans

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