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[ CAS No. 25414-22-6 ] {[proInfo.proName]}

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Chemical Structure| 25414-22-6
Chemical Structure| 25414-22-6
Structure of 25414-22-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 25414-22-6 ]

CAS No. :25414-22-6 MDL No. :MFCD00003227
Formula : C5H6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 98.10 Pubchem ID :-
Synonyms :

Safety of [ 25414-22-6 ]

Signal Word:Danger Class:3
Precautionary Statements:P210 UN#:1993
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 25414-22-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 25414-22-6 ]

[ 25414-22-6 ] Synthesis Path-Downstream   1~22

  • 2
  • [ 25414-22-6 ]
  • [ 20300-02-1 ]
  • 7-Amino-benzo[b]thiophene-4-carboxylic acid methyl ester [ No CAS ]
  • 2-Methoxy-5-thiophen-2-yl-1H-pyrrole-3-carbaldehyde [ No CAS ]
  • 3
  • [ 25414-22-6 ]
  • [ 64559-06-4 ]
  • 4-Amino-7-methoxy-naphthalene-1-carboxylic acid methyl ester [ No CAS ]
  • 4-Amino-8-methoxy-naphthalene-1-carboxylic acid methyl ester [ No CAS ]
  • 2-Methoxy-5-(3-methoxy-phenyl)-1H-pyrrole-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 23% 2: 11% 3: 48% In benzene for 10h; Irradiation;
1: 23% 2: 11% 3: 48% In benzene for 20h; Ambient temperature; Irradiation;
  • 4
  • [ 25414-22-6 ]
  • [ 144584-29-2 ]
  • 4,5-dimethoxy-8-hydroxyquinoline [ No CAS ]
  • 4,8-dimethoxy-5-hydroxyquinoline [ No CAS ]
  • 5
  • [ 25414-22-6 ]
  • [ 67-56-1 ]
  • [ 2896-67-5 ]
  • (1R,2R,6R,7S)-4,4,9,9-Tetramethoxy-7-methyl-3-oxa-tricyclo[5.2.2.02,6]undec-10-en-8-one [ No CAS ]
  • 6
  • [ 25414-22-6 ]
  • [ 37488-45-2 ]
  • methyl 5-(pyrrol-2-yl)pyrrole-3-carboxylate [ No CAS ]
  • 2-methoxy-5-(pyrrol-2-yl)pyrrole-3-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 39% 2: 12% In methanol for 20h; Irradiation;
  • 7
  • [ 25414-22-6 ]
  • [ 67-56-1 ]
  • [ 41264-06-6 ]
  • (1R,2R,6R,7R)-4,4-Dimethoxy-1,11-dimethyl-8-oxo-3,9-dioxa-tricyclo[5.2.2.02,6]undec-10-ene-10-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; for 168h;
  • 8
  • [ 25414-22-6 ]
  • [ 41264-06-6 ]
  • 4-methoxycarbonylmethyl-2,6-dimethyl-benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% In methanol for 50h; Heating;
  • 9
  • [ 25414-22-6 ]
  • [ 67-56-1 ]
  • [ 42933-07-3 ]
  • (1R,2R,6S,7R)-7-Bromo-4,4-dimethoxy-8-oxo-3,9-dioxa-tricyclo[5.2.2.02,6]undec-10-ene-10-carboxylic acid methyl ester [ No CAS ]
  • 10
  • [ 25414-22-6 ]
  • [ 504-31-4 ]
  • (1S,2S,6S,7R)-3,9-Dioxa-tricyclo[5.2.2.02,6]undec-10-ene-4,8-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% In methanol at 90℃; for 72h;
  • 11
  • [ 25414-22-6 ]
  • [ 14963-96-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91.8 percent / benzene / 2 h / Heating 2: 77 percent / CF3CO2H,(CH3CO)2O / 1 h / Heating
  • 12
  • [ 25414-22-6 ]
  • [ 123-73-9 ]
  • dichloroacetic acid (DCA) [ No CAS ]
  • [ 346440-54-8 ]
  • [ 110-00-9 ]
YieldReaction ConditionsOperation in experiment
95% In diethyl ether; chloroform; To a 2-dram vial equipped with a magnetic stir bar and charged with (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (24.6 mg, 0.100 mmol) was added CHCl3 (4.00 mL), dichloroacetic acid (DCA) (8.2 μL, 0.10 mmol) and (E)-crotonaldehyde (250 μL, 3.00 mmol). The solution cooled to -40 C. and stirred for 10 min before the addition of 2-methoxyfuran (92 μL, 1.00 mmol) in one portion. After stirring at -40 C. for 5 h, the reaction mixture was then transferred cold through a silica gel plug with Et2O and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (10% Et2O/petroleum ether) to provide the product as a colorless oil (131.3 mg, 78% yield, 95% ee). IR (film) 2973, 2937, 2837, 2726, 1725, 1617, 1589, 1458, 1438, 1385, 1341, 1261, 1227, 1177, 1054, 1017, 966.2, 942.4, 819.4, 744.0 cm-1; 1H NMR (300 MHz, CDCl3) δ9.73 (t, J=2.2 Hz, 1H, CHO), 5.85 (dd, J=2.8, 3.3 Hz, 1H, ArH), 4.99 (d, J=3.0 Hz, 1H, ArH), 3.79 (s, 3H, OCH3), 3.30 (sextet, J=0.8, 1H, CHCH3), 2.74 (ddd, J=2.2, 6.6, 17.0 Hz, 1H, CH2), 2.52 (ddd, J=2.2, 7.1, 17.0 Hz, 1H, CH2); 1.25 (d, J=6.9 Hz, 3H, CHCH3); 13C NMR (75 MHz, CDCl3) δ201.7, 160.8, 148.0, 105.4, 79.5, 57.9, 49.3, 28.1, 19.2; HRMS (CI) exact mass calcd for C9H12O3) requires m/z 168.0786, found m/z 168.0792. [α]D=-1.7 (c=1.0, CHCl3). The enantiomeric ratio was determined by GLC using an ASTEC Chiraldex Γ-TA column (80 C. isotherm, 1 mL/min); S isomer tr=79.3 min, R isomer tr=80.8 min.
  • 13
  • [ 25414-22-6 ]
  • [ 2058-72-2 ]
  • [ 1214750-15-8 ]
  • 14
  • [ 25414-22-6 ]
  • [ 253-52-1 ]
  • methyl-1a,7b-dihydro-1H-cyclopropa[a]naphthalene-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With 9,10-dimethyl-9,10-dibora-9,10-dihydroanthracene In diethylene glycol dimethyl ether at 140℃; for 96h; Inert atmosphere;
  • 15
  • [ 25414-22-6 ]
  • [ 1609119-99-4 ]
  • [ 84-85-5 ]
YieldReaction ConditionsOperation in experiment
79% With phenylmagnesium bromide In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; A typical procedure for the aryne generation from ortho-sulfinylaryl triflate 1 General procedure: To a mixture of 2-(4-tolylsulfinyl)phenyl triflate (1a) (87.4 mg, 0.240 mmol) and 1,3-diphenylisobenzofuran (2) (54.1 mg, 0.200 mmol) dissolved in THF (2.5 mL) was slowly added phenylmagnesium bromide (1.05 M, THF solution, 0.343 mL, 0.360 mmol) at -78 °C. After stirring for 10 min at the same temperature, to the mixture was added an aqueous phosphate buffer solution (pH 7, 10 mL). The mixture was extracted with EtOAc (10 mL × 3), and the combined organic extract was washed with brine (5 mL), dried (Na2SO4), and after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica-gel 10 g, n-hexane/EtOAc = 50/1) to give 9,10-diphenyl-9,10-dihydro-9,10-epoxyanthracene (3a) (69.3 mg, 0.200 mmol, quant.) as a colorless solid.
  • 16
  • [ 25414-22-6 ]
  • [ 802919-90-0 ]
  • [ 1609470-26-9 ]
  • 17
  • [ 25414-22-6 ]
  • [ 23680-40-2 ]
  • C9H9BrO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; for 24h;Reflux; Inert atmosphere; General procedure: Methyl 3-bromopropiolate 2 (0.5 mmol), furan 1 (0.6 mmol) and distilled toluene (1.5 mL) were added to atwo-necked flask, and the mixture was stirred at reflux for 24 h under nitrogen atmosphere. After completion ofthe initial DielsAlder reaction, silica gel (150 mg) was added under flow of nitrogen and the mixture wasstirred at reflux for 2 h. After removal of the solvent and filtration, a product 4 was purified by silica gelcolumn chromatography or PTLC using a mixture of ethyl acetate and n-hexane as an eluent.
  • 18
  • [ 25414-22-6 ]
  • [ 541539-88-2 ]
  • 5-methoxy-3-(5-methoxyfuran-2-yl)-2-methyl-2H-indazole [ No CAS ]
  • 19
  • [ 25414-22-6 ]
  • [ 4838-00-0 ]
  • 3-(5-methoxyfuran-2-yl)-2-methyl-2H-indazole [ No CAS ]
  • 20
  • [ 25414-22-6 ]
  • bis(3,5-bis(trifluoromethyl)phenyl)(2-triflyloxyphenyl)phosphine oxide [ No CAS ]
  • [ 84-85-5 ]
YieldReaction ConditionsOperation in experiment
59.8% With phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; A typical procedure for aryne generation from (2-triflyloxyaryl)phosphine oxides General procedure: To a mixture of bis(3,5-bis(trifluoromethyl)phenyl)(2-triflyloxyphenyl)phosphineoxide (1c) (135 mg, 0.193 mmol) and benzyl azide (2) (0.120 mL, 0.965 mmol) dissolved in THF (2.0 mL) was slowly added phenylmagnesium bromide (1.25 M, THF solution, 0.309 mL, 0.386 mmol) at room temperature. After stirring for 15 min at the same temperature, to the mixture was added an aqueous saturated solution of NH4Cl (2mL). The mixture was extracted with EtOAc (10 mL × 3), and the combined organic extract was dried (Na2SO4), and after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica-gel12 g, n-hexane/EtOAc = 9/1 to 8/2), and then by preparative TLC (CH2Cl2/EtOAc =29/1) to give 1-benzyl-1H-benzo[d][1,2,3]triazole (3a) (28.5 mg, 0.136 mmol, 70.5%)as a colorless solid.
  • 21
  • [ 25414-22-6 ]
  • [ 1418634-07-7 ]
  • 4-(5-methoxyfuran-2-yl)-7-methoxy-3,4-dihydrobenzo[e][1,2,3]oxathiazine 2,2-dioxide [ No CAS ]
  • 4-(5-methoxyfuran-2-yl)-7-methoxy-3,4-dihydrobenzo[e][1,2,3]oxathiazine 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14 % ee Stage #1: 7-methoxybenzo[e][1,2,3]oxathiazine-2,2-dioxide With C38H33O4P In o-xylene at 20℃; for 0.166667h; Stage #2: 2-methoxyfuran In o-xylene at 20℃; for 48h; Overall yield = 83 %; enantioselective reaction; General Procedure for the Catalytic Asymmetric Aza-Friedel-Crafts Reaction of 2-Methoxyfuran with Cyclic N-sulfimines General procedure: To a solution of cyclic N-sulfimine 1 (0.10 mmol) in o-xylene (0.5 mL) was added catalyst PA11 (0.01 mmol). The solution was stirred at room temperature for 10 min and 2-methoxyfuran 2 (0.30 mmol) was then added in one portion. The reaction mixture was stirred at room temperature until cyclic N-sulfimine 1 was completely consumed, as determined by TLC. The resulting mixture was then diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The crude residue was purified by flash column chromatography with EtOAc/hexanes as eluent to afford desired product 3. The enantiomeric excess was determined using HPLC analysis.
  • 22
  • [ 25414-22-6 ]
  • [ 31827-04-0 ]
  • methyl-2-(5-methoxyfuran-2-yl)-3-oxoindoline-2-carboxylate [ No CAS ]
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