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12108 Sigma-Aldrich

(±)-cis-Bicyclo[3.2.0]hept-2-en-6-one

≥98.0%

  • CAS Number 13173-09-6

  • Empirical Formula (Hill Notation) C7H8O

  • Molecular Weight 108.14

  •  MDL number MFCD06798168

  •  PubChem Substance ID 329749621

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C8, Carbonyl Compounds, Chemical Synthesis, Ketones,
Quality Level   100
assay   ≥98.0% (GC)
  ≥98.0%
refractive index   n20/D 1.4820 (lit.)
  n20/D 1.483
bp   158-160 °C (lit.)
density   1.025 g/mL at 25 °C (lit.)
SMILES string   O=C1C[C@@H]2C=CC[C@H]12
InChI   1S/C7H8O/c8-7-4-5-2-1-3-6(5)7/h1-2,5-6H,3-4H2/t5-,6-/m0/s1
InChI key   LNLLHUHPGPKRBM-WDSKDSINSA-N

Description

General description

(±)-cis-bicyclo(3.2.0)hept-2-en-6-one undergoes preparative scale Baeyer–Villiger biooxidation at high concentration using recombinant Escherichia coli biocatalyst and adsorbent resin (in situ substrate feeding and product removal).

Application

(±)-(1S,5R)-cis-bicyclo(3.2.0)hept-2-en-6-one may be used:
• to study enantioselective Baeyer–Villiger oxidation of (±)-cis-bicyclo(3.2.0)hept-2-en-6-one with H2O2 mediated by Co(Salen) catalyst in water with surfactants
• to investigate the extremophile enzymes (monooxygenase and hydrolases) in microorganisms isolated from deep-water petroleum reservoir and at high temperatures using fluorogenic assays and multibioreactions
• in the preparation of series of chalcone derivatives via reacton with arylaldehydes

Packaging

10, 50 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

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Protocols & Articles

Articles

Baeyer-Villiger Oxidation Reaction

The Baeyer–Villiger reaction involves the oxidation of ketones to esters by C-C bond cleavage of the carbonyl group and the introduction of an oxygen atom adjacent to it.1 This reaction can be accomp...
Keywords: Asymmetric synthesis, Catalysis, Oxidations

Peer-Reviewed Papers
15

References

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