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Chemical Structure| 930-51-8 Chemical Structure| 930-51-8

Structure of Cyclopentylacetylene
CAS No.: 930-51-8

Chemical Structure| 930-51-8

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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 [ 930-51-8 ]

CAS No. :930-51-8
Formula : C7H10
M.W : 94.15
SMILES Code : C#CC1CCCC1
MDL No. :MFCD00013744
InChI Key :TXVJSWLZYQMWPC-UHFFFAOYSA-N
Pubchem ID :136725

Safety of [ 930-51-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H302-H319
Precautionary Statements:P210-P305+P351+P338
Class:3
UN#:3295
Packing Group:

Application In Synthesis of [ 930-51-8 ]

* 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 [ 930-51-8 ]

[ 930-51-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 773134-43-3 ]
  • [ 930-51-8 ]
  • [ 948306-18-1 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; at 80℃; for 3.0h; Intermediate 35; Preparation of 4-(cyclopropylethynyl)-2-(methylsulfonyl)benzoic acid; 4-Bromo-2-methanesulfonyl acid methyl ester (250 mg, 0.85 mmol) was dissolved in triethylamine (5 mL). To the mixture was added copper iodide (9.0 mg, 5 mol %), followed by PdCl2(PPh3)2 (32 mg, 5 mol %) and ethynylcyclopentane (0.135 ml, 1.0 mmol). The mixture was heated in a sealed pressure tube at 80 C. for 3 hours. After reaction completion, the triethylamine was removed under vacuum and the residue was dissolved in EtOAc and filtered through Celite. The organic layer was washed with water, brine, and dried (Na2SO4). After filtration and concentration under vacuum, the residue was purified by column chromatography on sililca gel using EtOAc-hexane (0-100% gradient) as eluent to give methyl 4-(cyclopropylethynyl)-2-(methylsulfonyl)benzoate (240 mg). The product was dissolved in 10 mL of MeOH and 10 mL of 2N LiOH and the mixture was refluxed overnight. The MeOH was evaporated and the basic layer was washed with EtOAc, acidified, and re-extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give the product (165 mg) as a beige solid. m/z=293 (M+1).
  • 2
  • [ 1445-39-2 ]
  • [ 930-51-8 ]
  • [ 1361537-63-4 ]
  • 3
  • [ 930-51-8 ]
  • [ 223575-69-7 ]
  • 3-cyclopentyl-1-(2-(thiazol-2-yl)phenyl)prop-2-yn-1-ol [ No CAS ]
  • 4
  • [ 930-51-8 ]
  • [ 223575-69-7 ]
  • 5-(cyclopentylidenemethyl)thiazolo[2,3-a]isoquinolin-4-ium trifluoromethanesulfonate [ No CAS ]
 

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