1393110-52-5

Basic information

• Product Name: C₈H₉F₃O₄S
• Synonyms: C₈H₉F₃O₄S
• CAS NO: 1393110-52-5
• Molecular Weight: 258.218
• Mol File: 1393110-52-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: C₈H₉F₃O₄S(CAS DataBase Reference)
• NIST Chemistry Reference: C₈H₉F₃O₄S(1393110-52-5)
• EPA Substance Registry System: C₈H₉F₃O₄S(1393110-52-5)

Safety Data

• Hazardous Substances Data: 1393110-52-5(Hazardous Substances Data)

Upstream product

• 89-82-7 pulegone 
• 1310340-07-8 (R)-3-methyl-6-(propan-2-ylidene)-1-cyclohexen-1-yl trifluoromethanesulfonate 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 

Downstream Products

• 1393110-47-8 C₂₄H₃₃BrN₂O₆ 
• 1393110-63-8 C₁₇H₂₇NO₅ 
• 1393110-64-9 C₂₁H₃₁BrN₂O₄ 
• 1393110-66-1 C₂₁H₃₁BrN₂O₄ 
• 1393110-49-0 C₁₂H₁₉NO₃ 
• 75337-05-2 (+)-(R)-4-methyl-2-cyclohexene-1-one 
• 116-28-9 huperzine A 
• 1391436-01-3 C₁₉H₂₅BrN₂O₄ 
• 1393110-75-2 C₁₉H₂₅BrN₂O₄ 
• 103548-82-9 (4aR,5R,10bR)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-prop[1]eno-1,7-phenanthrolin-8(7H)-one 
• 107965-41-3 (4aR,5S,10bR,12S)-12-methyl-2,3,4,4a,5,6-hexahydro-1H-5,10b-propano-1,7-phenanthrolin-8(7H)-one 
• 1391435-98-5 C₁₉H₂₇BrN₂O₄ 
• 1394002-81-3 C₁₉H₂₇BrN₂O₄ 

Relevant articles and documents

Divergent total synthesis of the lycopodium alkaloids huperzine A, huperzine B, and huperzine U

Huperzine A, huperzine B, and huperzine U are congeners isolated from the Chinese herb Huperzia serrata (=Lycopodium serratum) in minuscule amounts. The most efficient total synthesis of huperzine A, the first asymmetric total syntheses of huperzine B, and the first total synthesis of huperzine U have been achieved efficiently in overall yields of 17%, 10%, and 9%, respectively, each spanning 10-13 steps from (R)-pulegone. The featured steps include palladium-catalyzed Buchwald-Hartwig coupling and Heck cyclization reactions and an Ir-catalyzed olefin isomerization reaction. This work has established the absolute configurations of huperzine B and huperzine U and revealed that natural huperzine A, huperzine B, and huperzine U possess the same set of absolute stereochemistries, thus providing support for the potential role of huperzine B and huperzine U in the biosynthesis of huperzine A.

Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one

A three-step synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one (1) from (R)-(+)-pulegone (3), proceeding in 44% overall yield, is described. The sequence comprises vinyl triflate formation, site-selective ozonolysis, and reduction. The route requires only one chromatographic purification and provides a convenient method to access multigram quantities of (R)-(+)-4-methylcyclohex- 2-ene-1-one (1).

An efficient total synthesis of (-)-huperzine A

The total synthesis of Lycopodium alkaloid (-)-huperzine A has been accomplished in 10 steps with 17% overall yield from commercially abundant (R)-pulegone. The synthetic route features an efficient synthesis of 4 via a Buchwald-Hartwig coupling reaction,