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Chemical Structure| 931-48-6 Chemical Structure| 931-48-6

Structure of 931-48-6

Chemical Structure| 931-48-6

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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 [ 931-48-6 ]

CAS No. :931-48-6
Formula : C8H12
M.W : 108.18
SMILES Code : C#CC1CCCCC1
MDL No. :MFCD00001513
InChI Key :SSDZYLQUYMOSAK-UHFFFAOYSA-N
Pubchem ID :70263

Safety of [ 931-48-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210
Class:3
UN#:3295
Packing Group:

Application In Synthesis of [ 931-48-6 ]

* 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 [ 931-48-6 ]

[ 931-48-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1445-39-2 ]
  • [ 931-48-6 ]
  • [ 1361537-61-2 ]
  • 2
  • [ 4805-22-5 ]
  • [ 931-48-6 ]
  • [ 1418113-15-1 ]
YieldReaction ConditionsOperation in experiment
34% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; diisopropylamine; at 0 - 55℃; for 16.33h;Inert atmosphere; Diisopropylamine (150 mL), CuI (0.31 g, 1.63 mmol), Pd(dppf)Cl2 (0.44 g, 0.54 mmol) and 5,5′-dibromo-2,2′-bithiophene (8.82 g, 27.2 mmol) were placed in flask and degassed with nitrogen at 0 C for 20 min. After cyclohexylacetylene (3 g, 27.7 mmol) was added, the mixture was heated at 55 C for 16 h. The mixture was poured into water, extracted with diethyl ether, and dried over MgSO4. The solvent was removed by rotary evaporation. The crude product was purified by column chromatography using n-hexane as the eluent. Yield: 4.5 g (34%). mp: 64 C, IR (KBr, cm-1); 3083 (aromtic C-H), 2970 (aliphatic C-H), 2217 (C≡C) 1H NMR (300 MHz, CDCl3, ppm): δ 7.00 (s, 1H), 6.97 (s, 1H), 6.94 (s, 1H), 6.89 (s, 1H), 2.63 (q, 1H), 1.82 (m, 5H), 1.46 (m, 5H). 13C NMR (75 MHz, CDCl3): δ138.4, 136.2, 131.6, 130.6, 123.8, 123.6, 123.5, 111.2, 100.0, 73.4, 32.4, 30.0, 25.8, 24.9. MS (m/z): [M+] = 349.9.
  • 3
  • [ 6214-35-3 ]
  • [ 931-48-6 ]
  • 5-[1-Cyclohexyl-meth-(Z)-ylidene]-5H-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine; In 1,4-dioxane; at 25 - 80℃; for 3.5h;Inert atmosphere; General procedure: (a) The reaction was performed in a bigger scale using 100 mg of 10% Pd/C (0.092 mmol), PPh3 (0.37 mmol), CuI (0.184 mmol), Et3N (10.68 mmol), compound 1a (3.56 mmol), and acetylenic compound 2a (5.32 mmol) in 1,4-dioxane (20.0 mL). After stirring at 80 C for 3 h under nitrogen the mixture was cooled to room temperature. The Pd/C was filtered off and washed with water (2 10 mL), acetone (2 10 mL), and EtOAc (2 10 mL). Then the catalyst was collected, dried at 100 C in an oven, and reused for the next run. The co-catalyst CuI along with PPh3 was added in every repeated run. (b) General method for the preparation of 3: A mixture of compound 1 (0.89 mmol), 10% Pd/C (0.023 mmol), PPh3 (0.092 mmol), CuI (0.046 mmol), and Et3N (2.67 mmol) in 1,4-dioxane (5.0 mL) was stirred at 25 C for 30 min under nitrogen. The acetylenic compound 2 (1.33 mmol) was added slowly with stirring. The mixture was then stirred at 80 C for 3 h, cooled to room temperature, diluted with EtOAc (30 mL), and filtered through celite. The filtrate was collected and concentrated. The residue was purified by column chromatography (2-15% EtOAc/hexane) to afford the desired product
  • 4
  • [ 55671-55-1 ]
  • [ 931-48-6 ]
  • [ 7732-18-5 ]
  • [ 57002-01-4 ]
  • 5
  • [ 55671-55-1 ]
  • [ 931-48-6 ]
  • [ 57002-01-4 ]
  • 6
  • [ 931-48-6 ]
  • [ 19591-17-4 ]
  • N-(2-(cyclohexylethynyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile; at 20℃;Inert atmosphere; General procedure: <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100.0 mg, 0.38 mmol, 1.0 equiv) in CH3CN (5.0 mL) was added sequentially with PdCl2(PPh3)2 (5.4 mg, 0.01 mmol, 0.02 equiv), Ph3P (4.0 mg, 0.02 mmol, 0.04equiv), 1-chloro-4-ethynylbenzene (57.6 mg, 0.42 mmol, 1.1 equiv). The resulting solution was degassed by passing through a steady stream of argon for 30 min (flask 1). In the meantime in another flask, a mixture of CuI (3.0 mg, 0.02 mmol, 0.04 equiv) in Et3N was also degassed bypassing through a steady stream of argon for 30 min (flask 2). After degassing, the mixture ofCuI in Et3N in flask 2 was transferred into the solution in flask 1 using a syringe with wide-boarneedle which resulted in the reaction solution turning yellow and giving white precipitates. The reaction mixture was allowed to stir at room temperature overnight and was quenched byaddition with sat. aq. NH4Cl. The separated aqueous phase was extracted with EtOAc (3x times).The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30-50% EtOAc-hexane to yield 114.6 mg of compound 1d (>99%)as a white solid.
 

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