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Chemical Structure| 946-38-3 Chemical Structure| 946-38-3

Structure of 946-38-3

Chemical Structure| 946-38-3

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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.

Alternative Products

Product Details of [ 946-38-3 ]

CAS No. :946-38-3
Formula : C12H14O2
M.W : 190.24
SMILES Code : O=C([C@H]1[C@@H](C2=CC=CC=C2)C1)OCC
MDL No. :MFCD08743330

Safety of [ 946-38-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 946-38-3 ]

* 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 [ 946-38-3 ]

[ 946-38-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 946-38-3 ]
  • [ 939-89-9 ]
  • [ 939-90-2 ]
  • 2
  • [ 946-38-3 ]
  • [ 939-89-9 ]
YieldReaction ConditionsOperation in experiment
i) c/s-(+/-)-2-Phenyl-cyclopropanecarboxylic acid; A solution of c/s-(+/-)-2-phenyl-cyclopropanecarboxylic acid ethyl ester (330 mg, 1.87 mmol) in MeOH (1 mL) was added to KOH (314 mg, 5.61 mmol) in MeOH (2 mL) at 0 °C. The mixture was stirred at room temperature overnight and then poured into water and extracted with CH2CI2. The organic layer was discarded and the aqueous phase was acidified with 10percent HCI and extracted with CH2CI2 (x2). The combined organic phases were dried over Na2SO4 and all volatiles were removed under EPO <DP n="75"/>vacuum. The acid was isolated as white powders and further purified by recrystallization from hexane (233 mg).
  • 3
  • [ 64-17-5 ]
  • [ 939-89-9 ]
  • [ 946-38-3 ]
  • 4
  • [ 946-38-3 ]
  • [ 939-89-9 ]
  • 5
  • [ 946-38-3 ]
  • [ 185256-47-7 ]
  • 6
  • [ 100-42-5 ]
  • [ 623-73-4 ]
  • [ 5932-30-9 ]
  • [ 946-39-4 ]
  • ethyl-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylate [ No CAS ]
  • [ 946-38-3 ]
 

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