183279-74-5

Basic information

• Product Name: 2H-Pyran-2-one, tetrahydro-3-(trifluoroacetyl)-, (+)- (9CI)
• Synonyms: (+)-3-(Trifluoroacetyl)tetrahydro-2-pyrone
• CAS NO: 183279-74-5
• Molecular Formula: C7H7F3O3
• Molecular Weight: 0
• Product Categories: ACETYLHALIDE
• Mol File: 183279-74-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Pyran-2-one, tetrahydro-3-(trifluoroacetyl)-, (+)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-one, tetrahydro-3-(trifluoroacetyl)-, (+)- (9CI)(183279-74-5)
• EPA Substance Registry System: 2H-Pyran-2-one, tetrahydro-3-(trifluoroacetyl)-, (+)- (9CI)(183279-74-5)

Safety Data

• Hazardous Substances Data: 183279-74-5(Hazardous Substances Data)

Upstream product

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 

Relevant articles and documents

Engineered cytochrome c-Catalyzed lactone-carbene B-H insertion

Previous work has demonstrated that variants of a heme protein, Rhodothermus marinus cytochrome c (Rma cyt c), catalyze abiological carbene boron-hydrogen (B-H) bond insertion with high efficiency and selectivity. Here we investigated this carbon-boron bond-forming chemistry with cyclic, lactone-based carbenes. Using directed evolution, we obtained a Rma cyt c variant BOR LAC that shows high selectivity and efficiency for B-H insertion of 5- A nd 6-membered lactone carbenes (up to 24,500 total turnovers and 97.1:2.9 enantiomeric ratio). The enzyme shows low activity with a 7-membered lactone carbene. Computational studies revealed a highly twisted geometry of the 7-membered lactone carbene intermediate relative to 5- A nd 6-membered ones. Directed evolution of cytochrome c together with computational characterization of key iron-carbene intermediates has allowed us to expand the scope of enzymatic carbene B-H insertion to produce new lactone-based organoborons.