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Chemical Structure| 2206-94-2 Chemical Structure| 2206-94-2

Structure of 2206-94-2

Chemical Structure| 2206-94-2

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Product Citations

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 [ 2206-94-2 ]

CAS No. :2206-94-2
Formula : C10H10O2
M.W : 162.19
SMILES Code : O=C(OC(=C)C=1C=CC=CC1)C
MDL No. :N/A

Safety of [ 2206-94-2 ]

Application In Synthesis of [ 2206-94-2 ]

* 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 [ 2206-94-2 ]

[ 2206-94-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2206-94-2 ]
  • [ 5906-98-9 ]
  • [ 222639-42-1 ]
YieldReaction ConditionsOperation in experiment
54% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In water; acetonitrile; at 80.0℃; for 8.0h; General procedure: To a stirred solution of vinyl acetate (0.3 mmol), TsNHNH2 (0.54 mmol) and TBAI (0.06 mmol) in MeCN (2 mL) was added TBHP (0.6 mmol, 70% aqueous solution) at room temperature. The mixture was heated at 80 oC for 8 h and cooled down to room temperature. The excess solvent was removed under vacuum, and the residue was purified by silica gel column chromatography to afford desired beta-keto-sulfones .
  • 2
  • [ 2206-94-2 ]
  • [ 14752-66-0 ]
  • [ 36603-45-9 ]
YieldReaction ConditionsOperation in experiment
87% With iodine; In water; acetonitrile; at 70℃; for 11.5h;Green chemistry; General procedure: A mixture of enol acetate 1 (1 mmol), sodium sulfinate 2 (1.2 mmol), I2 (1 mmol) and CH3CN + H2O (4:1,3 mL) was taken in a flask and stirred at 70 C for 10-12 h (Table 2). After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with ethyl acetate (3 x 5 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated unde rreduced pressure. The resulting crude product was purified by column chromatography using a mixture of hexane/ethyl acetate (4:1) as eluent to afford an analytically pure sample of product 3.
 

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