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Chemical Structure| 4079-54-3 Chemical Structure| 4079-54-3

Structure of 4079-54-3

Chemical Structure| 4079-54-3

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Product Details of [ 4079-54-3 ]

CAS No. :4079-54-3
Formula : C9H10O2
M.W : 150.17
SMILES Code : O=C(C1=CC=C(C)C=C1)CO
MDL No. :MFCD07778990
InChI Key :BFOWHGYYZRTDOV-UHFFFAOYSA-N
Pubchem ID :317549

Safety of [ 4079-54-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 4079-54-3 ]

* 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 [ 4079-54-3 ]

[ 4079-54-3 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 65143-37-5 ]
  • [ 4079-54-3 ]
YieldReaction ConditionsOperation in experiment
6 g With hydrogenchloride; water; In ethanol;Reflux; General procedure: α-bromo-3’-chloroacetophenone (6a, 17.5 g, 75 mM) in ethanol (100 mL) was refluxed for 10 h with anhydrous sodium acetate (6.2 g, 76 mM). The mixture was diluted with water and the solid which separated was collected and recrystallized from ethyl acetate. Then the solid (2-(3-chlorophenyl)-2-oxoethyl acetate, 10.4 g, 49 mM, 65%) in ethanol (50 mL) and hydrochloric acid (50 mL of 1 M) was refluxed for 6 h. The mixture was diluted with water and was then extracted with ethyl acetate. The extract was dried (sodium sulfate) and concentrated to give 2a (6.8 g, 40 mM, 53%).
  • 2
  • [ 54731-27-0 ]
  • [ 4079-54-3 ]
  • 3
  • 1-(phenylsulfenyl)-2-(p-tolyl)-1,2-bis(trifluoroacetoxy)ethane [ No CAS ]
  • [ 4079-54-3 ]
  • 4
  • [ 122-00-9 ]
  • [ 4079-54-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a stirred solutionof the corresponding α-aryl ketones (32 mmol, 1.0 equiv.) and powderedpotassium hydroxide (176 mmol, 5.5 equiv.) in 80 mL methanol was added iodobenzenediacetate (35 mmol, 1.1 equiv) slowly at 0 C. The reaction mixturewas kept at room temperature until TLC indicated the total consumption of the α-arylketones. Then the whole reaction mixture was concentrated. The residue wasshaken with water and ethyl acetate. The combined organic layer was evaporatedunder reduced pressure. The residue was dissolved in a mixture of 20 mL methanoland 20 mL 2 M aqueous hydrochloric acid and then stirred overnight at roomtemperature, and then filtered. The solid was washed with hexanes, and the obtained1-aryl-2-hydroxypropan-1-one 1 wasused directly for the next step without further purifications.1
References: [1]Journal of Chemical Research,2006,p. 32 - 33.
[2]Tetrahedron Letters,1992,vol. 33,p. 6065 - 6068.
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 5257 - 5262.
[4]Synthetic Communications,2002,vol. 32,p. 1875 - 1879.
[5]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 2351 - 2356.
[6]Synthesis,2008,p. 3205 - 3208.
[7]Tetrahedron Letters,1981,vol. 22,p. 1283 - 1286.
[8]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1987,vol. 26,p. 475 - 480.
[9]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1987,vol. 26,p. 475 - 480.
[10]Synthetic Communications,1997,vol. 27,p. 4079 - 4084.
[11]Journal of Organic Chemistry,2002,vol. 67,p. 2556 - 2565.
[12]Organic Preparations and Procedures International,2006,vol. 38,p. 473 - 476.
[13]Chemical Communications,2001,p. 956 - 957.
[14]Chemical Communications,2001,p. 956 - 957.
[15]Tetrahedron Letters,1982,vol. 23,p. 2917 - 2920.
[16]Tetrahedron Letters,2016,vol. 57,p. 658 - 662.
[17]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5708 - 5713.
[18]Journal of the American Chemical Society,2016,vol. 138,p. 11093 - 11096.
[19]Advanced Synthesis and Catalysis,2018,vol. 360,p. 744 - 750.
[20]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2861 - 2864.
[21]Organic Letters,2018,vol. 20,p. 6033 - 6036.
[22]Chemical Communications,2018,vol. 54,p. 12182 - 12185.
[23]Chemistry - A European Journal,2018,vol. 24,p. 19156 - 19161.
[24]Chemical Communications,2019,vol. 55,p. 4079 - 4082.
[25]Organic Letters,2019,vol. 21,p. 6674 - 6678.
[26]Journal of Organic Chemistry,2019,vol. 84,p. 11945 - 11957.
[27]Journal of the American Chemical Society,2020,vol. 142,p. 9982 - 9992.
[28]Organic Letters,2020,vol. 22,p. 7158 - 7163.
[29]Organic Letters,2021,vol. 23,p. 4715 - 4720.
[30]Green Chemistry,2022,vol. 24,p. 2919 - 2926.
[31]Advanced Synthesis and Catalysis,2022,vol. 364,p. 1757 - 1762.
  • 5
  • 2-methylthio-3-(4-methylphenyl)oxirane [ No CAS ]
  • [ 4079-54-3 ]
  • 6
  • 2-(1,5-dithiahexyl)-3-(4-methylphenyl)oxirane [ No CAS ]
  • [ 4079-54-3 ]
  • 7
  • [ 13154-24-0 ]
  • [ 4079-54-3 ]
  • 1-p-Tolyl-2-triisopropylsilanyloxy-ethanone [ No CAS ]
  • 8
  • [ 4079-54-3 ]
  • [ 107-30-2 ]
  • 2-methoxymethoxy-1-<i>p</i>-tolyl-ethanone [ No CAS ]
  • 10
  • [ 67-56-1 ]
  • [ 122-00-9 ]
  • [ 54149-77-8 ]
  • [ 4079-54-3 ]
  • 11
  • 2-halo-4'-methylacetophenone [ No CAS ]
  • [ 4079-54-3 ]
  • 12
  • [ 357943-48-7 ]
  • [ 4079-54-3 ]
  • 13
  • [ 17263-64-8 ]
  • [ 4079-54-3 ]
  • 15
  • [ 32315-10-9 ]
  • [ 18328-11-5 ]
  • [ 4079-54-3 ]
  • (2S,3R)-2,3-carbonyldioxy-1-(4-methylphenyl)-6-phenyl-1-hexanone [ No CAS ]
  • (2R,3S)-2,3-carbonyldioxy-1-(4-methylphenyl)-6-phenyl-1-hexanone [ No CAS ]
  • (2R,3R)-2,3-carbonyldioxy-1-(4-methylphenyl)-6-phenyl-1-hexanone [ No CAS ]
  • 16
  • [ 4079-54-3 ]
  • [ 66-25-1 ]
  • [ 77-76-9 ]
  • (2S,3R)-2,3-dihydroxy-2,3-O-isopropylidene-1-(4-methylphenyl)-1-octanone [ No CAS ]
  • (2R,3R)-2,3-dihydroxy-2,3-O-isopropylidene-1-(4-methylphenyl)-1-octanone [ No CAS ]
  • (2R,3S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(4-methylphenyl)-1-octanone [ No CAS ]
  • 17
  • [ 18328-11-5 ]
  • [ 4079-54-3 ]
  • [ 77-76-9 ]
  • (2S,3R)-2,3-dihydroxy-2,3-O-isopropylidene-1-(4-methylphenyl)-6-phenyl-1-hexanone [ No CAS ]
  • (2R,3R)-2,3-dihydroxy-2,3-O-isopropylidene-1-(4-methylphenyl)-6-phenyl-1-hexanone [ No CAS ]
  • (2R,3S)-2,3-dihydroxy-2,3-O-isopropylidene-1-(4-methylphenyl)-6-phenyl-1-hexanone [ No CAS ]
  • 18
  • [ 13603-62-8 ]
  • [ 4079-54-3 ]
YieldReaction ConditionsOperation in experiment
89% With N-Bromosuccinimide; In methanol; water; at 20℃; for 5.5h;Green chemistry; General procedure: Aromatic alcohol (1-2 mmol) was dissolved in methanol (or acetone in somecases, 2-4 mL) at room temperature, followed by addition of the aqueous solutionof N-bromosuccinimide (1.5 eq.=alcohol) with continuous stirring. GMP-b-CD (3,100mg=mmol of alcohol) were added in the reaction mixture and stirring was continued.Progress of the reaction was monitored by TLC until the reaction was completed(4-6 h). GMP was separated by filtration after completion of the reaction. Thereaction mixture was extracted with ethyl acetate (45 mL), combined organiclayers were dried over Na2SO4, and solvent was removed under reduced pressure.The product was further purified by flash column chromatography and analyzedby NMR spectroscopy.
  • 19
  • [ 50-00-0 ]
  • [ 1218-89-9 ]
  • [ 4079-54-3 ]
  • (S)-2-hydroxy-1,2-bis(4-methylphenyl)ethan-1-one [ No CAS ]
  • 20
  • [ 4079-54-3 ]
  • (E)-N-(2-methylbenzylidene)-P,P-diphenylphosphinic amide [ No CAS ]
  • C29H28NO3P [ No CAS ]
  • 2-hydroxy-1-(4-methylphenyl)-3-(2-methylphenyl)-3-[N-di(2-methylphenyl)phosphinoylamino]-1-propanone [ No CAS ]
  • C29H28NO3P [ No CAS ]
  • 22
  • [ 139016-20-9 ]
  • [ 1075-47-4 ]
  • [ 4079-54-3 ]
  • 23
  • [ 4079-54-3 ]
  • [ 98837-46-8 ]
  • 2-hydroxy-1-(4-methylphenyl)-3-(N-diphenylphosphinoylamino)-3-phenylpropan-1-one [ No CAS ]
  • 2-hydroxy-1-(4-methylphenyl)-3-(N-diphenylphosphinoylamino)-3-phenylpropan-1-one [ No CAS ]
  • 2-hydroxy-1-(4-methylphenyl)-3-(N-diphenylphosphinoylamino)-3-phenylpropan-1-one [ No CAS ]
  • 24
  • [ 4079-54-3 ]
  • [ 98837-46-8 ]
  • 2-hydroxy-1-(4-methylphenyl)-3-(N-diphenylphosphinoylamino)-3-phenylpropan-1-one [ No CAS ]
  • 2-hydroxy-1-(4-methylphenyl)-3-(N-diphenylphosphinoylamino)-3-phenylpropan-1-one [ No CAS ]
  • 26
  • [ 619-41-0 ]
  • [ 4079-54-3 ]
YieldReaction ConditionsOperation in experiment
53% With anhydrous sodium formate; In methanol; for 12h;Reflux; A mixture of 10d (3.0 mmol) and sodium formate (8.0equiv.) in 9 mL MeOH was heated to reflux for 12 h. After the reaction was completed, the mixturewas cool to room temperature, and ethanol was removed in vacuum, diluted with water (10 mL),aqueous layer was extracted with ethyl acetate (3 × 20 mL), and the combined organic phases weredried over Na2SO4, filtered and concentrated. After evaporation, the crude residue was purified bysilica gel column chromatography (200-300 mesh) using petroleum ether and ethyl acetate (15:1, v/v)as eluent to give target compound 15d: Light yellow solid, yield 53%.
  • 27
  • [ 4209-24-9 ]
  • [ 4079-54-3 ]
  • 28
  • [ 4079-54-3 ]
  • [ 139016-20-9 ]
  • [ 179914-05-7 ]
  • 29
  • [ 4079-54-3 ]
  • [ 139016-20-9 ]
YieldReaction ConditionsOperation in experiment
86.7%Chromat. With D-(+)-glucose; NADPH; at 20℃; for 6h;pH 6.5;aq. phosphate buffer; General procedure: In order to exclude the catalysis of heteroprotein and prove that the reactions were catalyzed by the recombinant protein, we conducted the reduction of ketones by using cell-free extract of E. coli BL21(DE3)/pET-21c and purified enzyme. The reaction mixture in 2 mL comprised 1 mL potassium phosphate buffer (pH 6.5, 0.1 M), 1 mL cell-free extract of E. coli BL21(DE3)/pET-21c (or 5 mg purified enzyme), 10 g/L glucose, NADPH and substrate. The mixture was shaken for 6 h at 20oC. After reaction, mixture was extracted with five volumes of ethyl acetate by vigorous mixing. The organic layer was analyzed by HPLC or GC. The results indicated that the reactions were catalyzed by the purified enzyme and the heteroprotein had no effect on the reactions. (Table 1)
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; f-amphol; hydrogen; sodium hydroxide; In isopropyl alcohol; at 20℃; under 15201.0 Torr; for 12h; Under argon atmosphere within the glove box, ligand L24 (Ar=3,5-(tBu)2C6H3) (12.9 mg, 0.0168mmol) and [Ir(COD)Cl]2 (5.4 mg, 0.008mmol) are added into a 2.5 ml vial. After dissolving in iPrOH (1.6 ml), at room temperature complexation for 1h to get the catalyst solution. The catalyst solution (10uL, 0.0001mmol) was added in the 5 ml of hydrogenation vial. Then sequentially add isopropanol solution of NaOH (0.05mmol/mL, 20uL, 0.001mmol), <strong>[4079-54-3]p-methyl-α-hydroxyacetophenone</strong> substrate (0.1mmol), 1 ml isopropanol solvent. Place the hydrogenation vial into the hydrogenation reactor. After replacing with hydrogen three time, place 20atm H2. At room temperature, react for 12h. After completion of reaction the release of hydrogen, the reaction mixture over a short silica gel column. NMR fixed conversion (> 99%), using high performance liquid chromatography (HPLC) assay reaction enantioselectivity ee value (> 99%).
  • 30
  • [ 4079-54-3 ]
  • 2-methoxymethoxy-1-<i>p</i>-tolyl-ethanone oxime [ No CAS ]
  • 31
  • [ 4079-54-3 ]
  • [ 217650-29-8 ]
  • 32
  • [ 4079-54-3 ]
  • <i>N</i>-(2-methoxymethoxy-1-<i>p</i>-tolyl-ethyl)-acetamide [ No CAS ]
  • 33
  • (+/-)S-2-(p-tolyl)-1-(phenylsulfinyl)ethene [ No CAS ]
  • [ 4079-54-3 ]
  • 34
  • [ 4079-54-3 ]
  • [ 1795-48-8 ]
  • isopropyl-carbamic acid 2-oxo-2-p-tolyl-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With triethylamine; In dichloromethane; benzene; (2) A mixture of <strong>[4079-54-3]2-hydroxy-1-p-tolyl-ethanone</strong> (5.6 g, 37 mmol), prepared in the previous step, isopropyl isocyanate (5.5 ml, 56 mmol) and triethylamine (5.16 ml, 37 mmol) in 100 ml of benzene was refluxed under nitrogen for approximately 23 hours. The solvent was removed under reduced pressure. The residue was dissolved in CH2 Cl2 and extracted with 1N HCl. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give 8.295 g of an oil. Crystallization of the oil from isopropyl alcohol gave isopropyl-carbamic acid 2-oxo-2-p-tolyl-ethyl ester (2.5267 g, 29%) as a light yellow solid, mp 130-133 C. Elemental Analysis for C13 H17 NO3, Calc'd: C, 66.36; H, 7.28; N, 5.95, Found: C, 66.02; H, 7.39; N, 5.93
  • 35
  • [ 4079-54-3 ]
  • [ 95-54-5 ]
  • [ 17286-62-3 ]
YieldReaction ConditionsOperation in experiment
90% With gallium(III) perchlorate; In ethanol; at 25℃; General procedure: Representative experimental procedure for the synthesis of 2-phenylquinoxaline (3a) (Table 2, entry 1): A mixture of o-phenylenediamine (1a, 0.0541 g, 0.5 mmol), 2-hydroxyaceto-phenone (2a, 0.0681 g, 0.5 mmol) and Ga(ClO4)3 (0.018g, 0.05 mmol) in EtOH (3 mL) was stirred at room temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was directly purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1) to afford the product 3a. The structures of all products were confirmed by IR, 1H NMR spectroscopy and melting points, which were consistent with literature data.
70% With triphenylantimony; In toluene; at 20℃; for 3h; General procedure: Triphenylstibane(35.5 mg, 0.1 mmol, 10 mol%) and diamine 2 (1.2 mmol) were added to a solution of -hydroxy ketone 1(1 mmol) in toluene (6 mL) under air. The solution was stirred at room temperature and monitored byTLC. The reaction mixture was concentrated under reduced pressure and the residue was purified bycolumn chromatography (CH2Cl2) on silica gel. The products were confirmed by comparison of mp,NMR data, and MS spectra with that in the literature. 822:
 

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Technical Information

• Appel Reaction • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Jones Oxidation • Lawesson's Reagent • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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