159651-24-8

Basic information

• Product Name: Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl- (9CI)
• Synonyms: Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl- (9CI)
• CAS NO: 159651-24-8
• Molecular Formula: C₉H₁₂O
• Molecular Weight: 136.19098
• Product Categories: ACETYLGROUP
• Mol File: 159651-24-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl- (9CI)(159651-24-8)
• EPA Substance Registry System: Ethanone, 1-(1S,2R,4S)-bicyclo[2.2.1]hept-5-en-2-yl- (9CI)(159651-24-8)

Safety Data

• Hazardous Substances Data: 159651-24-8(Hazardous Substances Data)

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 78-94-4 methyl vinyl ketone 

Downstream Products

• 475563-22-5 biperiden hydrochloride 
• 93778-71-3 C₁₅H₂₃NO 
• 163296-11-5 biperiden 

Relevant articles and documents

Facile Synthesis of a New Chiral BINOL–Silica Hybrid Catalyst for Asymmetric Diels–Alder and Aza Michael Reactions

Abstract: A novel chiral BINOL–silica hybrid has been successfully prepared by the reaction of (S)-BINOL and SiCl4 following by gel polymerization under atmosphere condition. The synthesized catalyst was characterized by elemental analysis, Fourier-transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy and energy-dispersive X-ray spectroscopy. Catalytic activity of the chiral BINOL–silica hybrid for diastereo- and enantioselective Diels–Alder and aza Michael reactions has been investigated. Mild reaction conditions, high yields, excellent diastereo- and enantiomeric excess make this powerful and effective catalyst as an attractive option for the synthesis of chiral organic compounds. Graphical Abstract: [Figure not available: see fulltext.]

Enantioselective catalytic diels-alder reactions with enones as dienophiles

The aqua complexes (SM,RC)-[(η5-C 5Me5)M(PROPHOS)(H2O)][SbF6] 2 [PROPHOS = (R)-propane-1,2-diylbis(diphenylphosphane); M = Rh (1), Ir (2)] are active catalysts for the asymmetric Diels-Alder reaction between ketones and dienes. At low temperatures, enantioselectivities of up to 89% ee are achieved. The intermediate Lewis acid-dienophile complexes (S M,RC)-[(η5-C5Me 5)M(PROPHOS)(MVK)][SbF6]2 (MVK = methyl vinyl ketone; M = Rh (3), Ir (4)) and (SIr,RC)- [(η5-C5Me5)Ir(PROPHOS)(EVK)][SbF 6]2 (EVK = ethyl vinyl ketone (5)) have been isolated and characterized by analytical and spectroscopic means, including the determination of the crystal structure of the iridium complexes 4 and 5 by X-ray diffractometric methods. Structural parameters indicate that the dispositions of the coordinated dienophiles are controlled by the CH/π attractive interactions established between a phenyl group of the PROPHOS ligand and the α-vinyl proton of the ketones. Proton NMR parameters indicate that these interactions are maintained in solution. From these data, the stereoselectivity of the catalytic reaction is discussed.