292150-03-9

Basic information

• Product Name: Cyclohexanol, 2-fluoro-, (1S,2S)-
• CAS NO: 292150-03-9
• Molecular Formula: C6H11FO
• Molecular Weight: 118.151
• Mol File: 292150-03-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Cyclohexanol, 2-fluoro-, (1S,2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanol, 2-fluoro-, (1S,2S)-(292150-03-9)
• EPA Substance Registry System: Cyclohexanol, 2-fluoro-, (1S,2S)-(292150-03-9)

Safety Data

• Hazardous Substances Data: 292150-03-9(Hazardous Substances Data)

Upstream product

• 2549-51-1 vinyl chloroacetate 
• 14365-32-3 trans-2-fluorocyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 433933-74-5 (1S,2S)-(+)-2-fluorocyclohexyl N-phenylcarbamate 
• 433305-07-8 trans-1-acetoxy-2-fluorocyclohexane 
• 108-05-4 vinyl acetate 

Downstream Products

• 1350551-45-9 carbonic acid 1-(5-{(R)-(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxy)ethyl ester (1S,2S)-2-fluorocyclohexyl ester 
• 1350552-21-4 carbonic acid 1-chloroethyl ester (1S,2S)-2-fluorocyclohexyl ester 

Relevant articles and documents

Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system

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(Salen)chromium Complex Mediated Asymmetric Ring Opening of meso- And Racemic Epoxides with Different Fluoride Sources

The asymmetric ring opening of five meso-and three racemic epoxides with different fluorinating reagents in the presence of stoichiometric or slightly sub-stoichiometric amounts of Jacobsen's enantiopure (salen)chromium chloride complex A gave the corresponding optically active vicinal fluorohydrins. Silver fluoride was used as one of the fluoride sources either in the presence of Bu4N+H2F3- in diethyl ether or in acetonitrile. The latter reactions starting from cyclohexene oxide (1) showed maximum 72% ee in the formed fluorohydrin 2 isolated in 90% yield. From other meso-epoxides such as cyclopentene oxide and cycloheptene oxide the corresponding fluorohydrins were isolated in 80% and 82% yield with 65% and 62% ee, respectively. In case of ring opening under similar conditions of the racemic styrene oxide or phenyl glycidyl ether 83% and 75% of the fluorohydrins with fluorine in the primary position were isolated with 74% ee and 65% ee, respectively. Tetrahydronaphthalene oxide yielded a 2:1 mixture of trans- (23% ee) and cis-2-fluoro-3,4-benzocyclohexenol (2% ee) suggesting competing SN2 and SN1 type ring openings. Other epoxides such as cyclooctene oxide, cis-stilbene oxide and α-methylstyrene oxide did not react or gave the fluorohydrins with very small enantiomeric excess.

Enantioselective ring-opening of epoxides by HF-reagents: Asymmetric synthesis of fluoro lactones

The asymmetric ring opening of meso- and racemic-epoxides with different HF-reagents mediated by enantiopure (salen)chromium chloride provides optically active fluorohydrins with maximum 90% e.e. This reaction as well as lipase-catalyzed deracemization of