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Chemical Structure| 577-16-2 Chemical Structure| 577-16-2
Chemical Structure| 577-16-2

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2-Methylacetophenone is an endogenous metabolite.

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Product Citations

Siriboe, Mary G ; Vargas, David A ; Fasan, Rudi ;

Abstract: Chiral cyclopropanols are highly desirable building blocks for medicinal chemistry, but the stereoselective synthesis of these molecules remains challenging. Here, a novel strategy is reported for the diastereo- and enantioselective synthesis of cyclopropanol derivatives via the biocatalytic asymmetric cyclopropanation of vinyl esters with ethyl diazoacetate (EDA). A dehaloperoxidase enzyme from Amphitrite ornata was repurposed to catalyze this challenging cyclopropanation reaction, and its activity and stereoselectivity were optimized via protein engineering. Using this system, a broad range of electron-deficient vinyl esters were efficiently converted to the desired cyclopropanation products with up to 99.5:0.5 diastereomeric and enantiomeric ratios. In addition, the engineered dehaloperoxidase-based biocatalyst is able to catalyze a variety of other abiological carbene transfer reactions, including N−H/S−H carbene insertion with EDA as well as cyclopropanation with diazoacetonitrile, thus adding to the multifunctionality of this enzyme and defining it as a valuable new scaffold for the development of novel carbene transferases.

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Product Details of 2-Methylacetophenone

CAS No. :577-16-2
Formula : C9H10O
M.W : 134.18
SMILES Code : CC(C1=CC=CC=C1C)=O
MDL No. :MFCD00008734
InChI Key :YXWWHNCQZBVZPV-UHFFFAOYSA-N
Pubchem ID :11340

Safety of 2-Methylacetophenone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H227
Precautionary Statements:P210-P261-P271-P280-P302+P352-P304+P340-P312-P363-P370+P378-P403+P235-P501

Application In Synthesis of 2-Methylacetophenone

* 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 [ 577-16-2 ]

[ 577-16-2 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 383-63-1 ]
  • [ 577-16-2 ]
  • [ 163266-02-2 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; for 2h;Reflux; General procedure: Referring to Scheme 1, to the appropriate acetophenone derivative (0.05 mol) and ethyltrifluoroacetate (0.075 mol) in methanol (20 mL), sodium methoxide solution (0.1 mol of Na + 15 mL ofCH3OH) was added dropwise at room temperature, and the mixture was refluxed for 2 h. After themethanol was evaporated under vacuum, the residue was dissolved in ethyl acetate (50 mL), washedwith 5% HCl (25 mL) and water (25 mL), and dried over sodium sulfate. After the solvent wasevaporated under vacuum, the corresponding compound II was obtained.
  • 3
  • [ 611-14-3 ]
  • [ 22927-13-5 ]
  • [ 7287-82-3 ]
  • [ 577-16-2 ]
  • 4
  • [ 577-16-2 ]
  • [ 611-14-3 ]
YieldReaction ConditionsOperation in experiment
91% With triethylsilane; indium(III) bromide; In chloroform; at 60℃; for 1h;Inert atmosphere; General procedure: To a freshly distilled CHCl3 solution (0.6 mL) in a screw-capped vial under N2 atmosphere, InBr3 (10.6 mg, 0.0300 mmol), aromatic ketone 4 (0.6 mmol) and Et3SiH (383 muL, 2.40 mmol) was successively added. The resulting mixture was stirred at 60 C (bath temperature) or room temperature, and monitored by TLC or GC analysis until consumption of the starting ketone. The reaction was quenched with H2O. The aqueous layer was extracted with CH2Cl2 (5 mL × 3), the organic phases were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by a silica gel column chromatography (hexane/AcOEt = 19/1) to give the corresponding alkylbenzene 5. 1-Cyano-4-[1-(triethylsiloxy)ethyl]benzene (5k): 85% yield; colorless oil; 1H NMR (500 MHz, CDCl3) delta 0.54-0.62 (m, 6H), 0.90-0.93 (m, 9H), 1.41 (d, 3H, J = 6 Hz), 4.90 (q, 1H, J = 6 Hz), 7.45 (d, 2H, J = 8 Hz), 7.61 (d, 2H, J = 8 Hz); 13C NMR (125 MHz, CDCl3) delta 4.7, 6.7, 27.0, 69.9, 110.5, 119.0, 125.8, 132.0, 152.3; MS (ESI): m/z 284 (M++Na); HRMS (ESI): Calcd for C15H23NNaOSi: 284.1447, Found: 284.1407.
  • 5
  • [ 577-16-2 ]
  • [ 163266-02-2 ]
YieldReaction ConditionsOperation in experiment
64% 1F-a 1-(2-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione This intermediate was prepared from commercially available 2- methylacetophenone. The product obtained was a liquid which was isolated from the reaction mixture by extraction with a suitable solvent like Ethyl acetate. The evaporation of the solvent gave the diketo product in 64% yield which was used as such for the next step. IR (KBr) cm-1 at 1147 (aliphatic C=O), 1199 (CF3), 1458 (C-H) 1608 (aromatic C=O)
  • 6
  • [ 577-16-2 ]
  • [ 1332832-16-2 ]
  • 7
  • [ 577-16-2 ]
  • [ 611-14-3 ]
  • [ 64811-81-0 ]
  • [ 7287-82-3 ]
  • 8
  • [ 611-14-3 ]
  • [ 7287-82-3 ]
  • [ 42070-90-6 ]
  • [ 577-16-2 ]
YieldReaction ConditionsOperation in experiment
With [bis(acetoxy)iodo]benzene; chloro(5,10,15,20-tetrakis-(10-nitro-1,2,3,4,5,6,7,8-octahydro-1,4;5,8-dimethanoanthracen-9-yl)porphyrin) iron(III); In methanol; dichloromethane; water; for 2h;Inert atmosphere; General procedure: Iron porphyrin complex 5 (1.2 mg 1 mumol) and imidazole (0.34 mg, 10 mumol) were placed in a test tube under argon. Then, 1 ml of distilled CH2Cl2/MeOH/H2O mixture (0.5:0.4:0.1) was added, followed by ethylbenzene (106 mg, 1 mmol). PhI(OAc)2 (32 mg, 100 mumol) in 0.1 ml CH2Cl2 was added over a period of 1 h with a syringe-pump. After the addition of all the PhI(OAc)2, the reaction mixture was allowed to stir for an additional 1 h. The mixture was analyzed by GC for oxidation yield based on oxidant, 41 %, alcohol/ketone ratio, 83:17, and alcohol enantiomeric excess, 68 % (conditions used: 80 C (1 min), 1 C min-1 80-120 C, 2.5 C min-1 120-180 C). Polarimetric measurement of the oxidation product determined that (R)-(+)-1-phenyl ethanol was formed in excess. The reaction and analysis of the other substrates and catalysts in Table 3 were carried out in an identical manner with that used for ethylbenzene oxidation. Except for indane, the enantiomeric excess was determined by chiral HPLC with a Chiralcel OB-H column: n-hexane/isopropanol 95:5; flow rate: 0.5 ml min-1, detection: 220nm.
  • 9
  • [ 407-38-5 ]
  • [ 577-16-2 ]
  • [ 163266-02-2 ]
 

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