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[ CAS No. 1774-12-5 ] {[proInfo.proName]}

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Chemical Structure| 1774-12-5
Chemical Structure| 1774-12-5
Structure of 1774-12-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1774-12-5 ]

CAS No. :1774-12-5 MDL No. :MFCD00104791
Formula : C13H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 218.25 Pubchem ID :-
Synonyms :

Safety of [ 1774-12-5 ]

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 [ 1774-12-5 ]

* 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 [ 1774-12-5 ]

[ 1774-12-5 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 1774-12-5 ]
  • [ 61888-41-3 ]
YieldReaction ConditionsOperation in experiment
76% With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; 1.1 Step 1 Compound 1: 3-Chloro-5-(4-methoxy-phenyl)-cyclohex-2-enone MW : 236.70 Formula : C13H13C102 LCMS : 100% MH+=237 1H NMR (250 MHz, DMSO d6) ppm 7.27 (d, J = 8.6 Hz, 2H), 6.89 (d, J = 8.7 Hz, 2H), 6.30 (d, J = 1.92 Hz, 1H), 3.73 (s, 3H), 3.58-3.36 (m, 1H), 3.01 (m, 1H), 2.89-2.63 (m, 2H), 2.46-2.34 (m, 1H) A suspension of 12. Og (55.0mmol) of 5-[4-(Methoxyphenyl)]-1,3-cyclohexanedione with 5.5mL of DMF in 300mL of DCM was cooled to 0°C.Then, 5.6 mL (64.2mmol) of oxalyl chloride were added dropwise and the resulting solution was stirred 2h at room temperature. Water was added, the mixture was extracted with AcOEt, the combined organic layers were washed with water, dried over MgS04 and then evaporated under vacuum. The residue was purified by silica gel flash chromatography (DCM/ ethyl acetate 9/1) to give 9.9g (76%) of Compound 1 as a yellow oil which crystallised.
With chloroform; phosphorus trichloride
With sodium carbonate; trichlorophosphate In toluene
  • 2
  • [ 1774-12-5 ]
  • [ 913718-19-1 ]
YieldReaction ConditionsOperation in experiment
92% With bromine; acetic acid at 20℃; for 2h; 33 Experimental 33. 2-Bromo-5-(4-methoxyphenyl)cyclohexane-1,3-dione (82) [0356] To the vigorously stirred suspension of 5 -(4-methoxyphenyl)cycl ohexane- 1,3 - dione (2.18 g, 10 mmol) in acetic acid (20 ml) bromine (0.52 ml, 10 mmol) was added dropwise. The suspension became clear for a short time, and then the light yellow precipitate started toform. The newly formed suspension was stirred at r.t. for additional 2 hours. The reaction mixture was filtered off and precipitate was carefully washed with diethyl ether twice and dried thoroughly on air to give a title compound as a yellow powder. Yield: 2.74 g (92%)
With bromine; acetic acid
With tetrachloromethane; N-Bromosuccinimide
Multi-step reaction with 3 steps 1: H2SO4 2: CCl4; <i>N</i>-bromo-succinimide 3: aqueous H2SO4

  • 3
  • [ 943-88-4 ]
  • [ 105-53-3 ]
  • [ 1774-12-5 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: diethyl malonate With sodium ethanolate at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 4-(p-methoxyphenyl)-3-butene-2-one In ethanol at 100℃; for 12h; Inert atmosphere; Stage #3: With sodium hydroxide In ethanol; water at 120℃; for 2h; Inert atmosphere;
(i) NaOMe, MeOH, (ii) aq. NaOH, (iii) aq. HCl; Multistep reaction;
With sodium ethanolate Heating;
With sodium ethanolate Heating;
Stage #1: diethyl malonate With sodium ethanolate In ethanol at 0 - 20℃; for 0.5h; Stage #2: 4-(p-methoxyphenyl)-3-butene-2-one In ethanol Reflux; Further stages;

  • 4
  • [ 6286-46-0 ]
  • [ 1774-12-5 ]
  • 2-bromo-4,5-dimethoxy-benzoic acid 5-(4-methoxy-phenyl)-3-oxo-cyclohex-1-enyl ester [ No CAS ]
  • 5
  • [ 1774-12-5 ]
  • [ 1546-79-8 ]
  • [ 950908-43-7 ]
  • 6
  • [ 1774-12-5 ]
  • [ 4637-24-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
99% In chloroform at 20℃; for 0.5h; 5.3 Step 3: Synthesis of Compound 27 → Compound 28 27 0.011 mol of the compound was dissolved in chloroform (53 ml), After adding DMF-DMA (1.66 ml, 0.012 mmol) dropwise,The reaction mixture was stirred at rt for 30 minutes.After stirring, the solution was extracted with DCM. After drying over MgSO4, the solvent was removed under vacuum. The residue is 28 compounds. (99%)
at 20℃; for 0.0833333h;
In neat (no solvent) at 20℃; for 1h;
In dichloromethane at 20℃; for 1h;

  • 7
  • [ 1774-12-5 ]
  • [ 70291-62-2 ]
  • [ 1252048-01-3 ]
YieldReaction ConditionsOperation in experiment
70% With toluene-4-sulfonic acid In toluene Reflux;
  • 8
  • [ CAS Unavailable ]
  • [ 1774-12-5 ]
  • [ 1421059-01-9 ]
YieldReaction ConditionsOperation in experiment
59% With [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 1h; Irradiation; regioselective reaction; 1 4.2. General procedure for the one-pot, three-component synthesis of dihydrofurans 3 General procedure: A solution of 1,3-cyclohexanedione 1 (1.00-2.00 mmol), iodobenzene diacetate (1.00-2.00 mmol) and alkene 2 (4.05-14.71 mmol) in dichloromethane (10 mL) was irradiated (250 W) at room temperature for 40-360 min. The solvent was evaporated under reduced pressure, and the residue was purified by flash chromatography to afford fused dihydrofuran 3.
  • 9
  • [ 3240-34-4 ]
  • [ 1774-12-5 ]
  • [ 1415261-30-1 ]
YieldReaction ConditionsOperation in experiment
76% In dichloromethane at 20℃; for 2h; 1 General procedure for the preparation of iodonium ylides 4 General procedure: A solution of 1,3-cyclohexanedione 1 (10.00-30.00 mmol) and iodobenzene diacetate (10.00-30.00 mmol) in dichloromethane (200 mL) was stirred at room temperature for 120-180 min. The yellow solution was then washed with an aqueous 5% KOH solution (2*100 mL), water (2*50 mL) and dried (MgSO4). The solvent was evaporated under reduced pressure (water bath below 30 °C), the solid residue triturated with hexanes (100 mL) and filtered to afford iodonium ylide 4.
In dichloromethane at 20℃; for 2h;
With potassium hydroxide In methanol; water at 20℃; for 2h; Inert atmosphere;
With potassium hydroxide In methanol; water at 20℃; Inert atmosphere;
With potassium hydroxide In methanol at 20℃; for 2h;
With potassium hydroxide In methanol; water at 20℃;

  • 10
  • [ 1774-12-5 ]
  • [ 106-96-7 ]
  • [ 1426146-92-0 ]
YieldReaction ConditionsOperation in experiment
67% With dirhodium tetraacetate; [bis(acetoxy)iodo]benzene at 20℃; for 1.5h; General procedure for the synthesis of 2-(bromomethyl)furan 1a-n General procedure: To the flamed dried flask containing 1 mol% of Rh2(OAc)4 and 2 equiv of propargyl bromideand 1.1 equiv of PhI(OAc)2 was added, 1 equiv of 1,3-diketone. The semi-heterogenousreaction mixture was stirred at room temperature under solvent free condition for specifiedtime. At the end of this time a solution was obtained. The resulting green solution was driedunder reduced pressure and subjected to column chromatography to give, the correspondingproducts (3a to 3l, 3l’).
  • 11
  • [ 1774-12-5 ]
  • [ 399-25-7 ]
  • [ 108-24-7 ]
  • 2-amino-3-(2-fluorophenyl)-6-(4-methoxyphenyl)benzofuran-4-yl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% General procedure: To a solution of 1-aryl-2-nitroethylene (1.0equiv) and appropriate cyclohexane-1,3-dione (1.5equiv) in dry tetrahydrofuran (THF, 10mL) was added Et3N (0.2equiv) under argon. The mixture was stirred at room temperature for 6-12h followed by the addition of Et3N (2.0equiv), DMAP (0.2equiv) and Ac2O (2.0equiv). The resulting mixture was stirred at room temperature for 5-10h. After completion as monitored by TLC, the resulting mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel using n-hexane-dichloromethane as eluent to provide desired products.
  • 12
  • [ 22482-43-5 ]
  • [ 1774-12-5 ]
  • [ 108-24-7 ]
  • [ 2062655-40-5 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 2,6-dichloronitrostyrene; 5-(4-methoxyphenyl)-1,3-cyclohexanedione With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: acetic anhydride With dmap; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; 4.1.2 General procedure for synthesis of 4-acetoxy-2-amino-3-arylbenzofuran derivatives 9-27 General procedure: To a solution of 1-aryl-2-nitroethylene (1.0equiv) and appropriate cyclohexane-1,3-dione (1.5equiv) in dry tetrahydrofuran (THF, 10mL) was added Et3N (0.2equiv) under argon. The mixture was stirred at room temperature for 6-12h followed by the addition of Et3N (2.0equiv), DMAP (0.2equiv) and Ac2O (2.0equiv). The resulting mixture was stirred at room temperature for 5-10h. After completion as monitored by TLC, the resulting mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel using n-hexane-dichloromethane as eluent to provide desired products.
  • 13
  • [ 3179-10-0 ]
  • [ 1774-12-5 ]
  • [ 108-24-7 ]
  • [ 2062655-43-8 ]
YieldReaction ConditionsOperation in experiment
44% Stage #1: 1-methoxy-4-(2-nitro-vinyl)-benzene; 5-(4-methoxyphenyl)-1,3-cyclohexanedione With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: acetic anhydride With dmap; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; 4.1.2 General procedure for synthesis of 4-acetoxy-2-amino-3-arylbenzofuran derivatives 9-27 General procedure: To a solution of 1-aryl-2-nitroethylene (1.0equiv) and appropriate cyclohexane-1,3-dione (1.5equiv) in dry tetrahydrofuran (THF, 10mL) was added Et3N (0.2equiv) under argon. The mixture was stirred at room temperature for 6-12h followed by the addition of Et3N (2.0equiv), DMAP (0.2equiv) and Ac2O (2.0equiv). The resulting mixture was stirred at room temperature for 5-10h. After completion as monitored by TLC, the resulting mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel using n-hexane-dichloromethane as eluent to provide desired products.
  • 14
  • [ 34312-77-1 ]
  • [ 1774-12-5 ]
  • 2-amino-6-(4-methoxyphenyl)-3-(thiophen-2-yl)benzofuran-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With triethylamine In tetrahydrofuran for 12h; Reflux; 4.1.3 General procedure for synthesis of compound 28-29 and 30-47 General procedure: A mixture of the appropriate cyclohexane-1,3-dione (1.5equiv), trans-2-(2-nitrovinyl)thiophene (1.0equiv) and Et3N (2.0equiv) in dry THF (10mL) was stirred at reflux for 12h. After reaction completion as monitored by TLC, the resulting mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel using n-hexane-dichloromethane as eluent to provide 28 and 29. The appropriate 28 and 29 (1.0equiv) as the starting material followed by the addition commercially available alkyl halide (1.5equiv), K2CO3 (5equiv) and Cs2CO3 (5equiv) in acetone containing a catalytic amount of KI (0.2equiv). The reaction mixture was then allowed to stirred for 4-6hat reflux. The solvent was then removed by vacuum, and the reaction residue was diluted with ethyl acetate. The ethyl acetate layer was then washed with saturated Na2S2O3 aqueous, water, and brine. The organic fractions were dried over anhydrous MgSO4 and evaporated under vacuum. The residue was purified by flash chromatography on silica gel using methanol-dichloromethane or ethyl acetate-n-hexane (containing 0.1% Et3N) as eluent to provide products 30-47.
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