402587-14-8

Basic information

• Product Name: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE
• Synonyms: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE
• CAS NO: 402587-14-8
• Molecular Formula: C12H22O3
• Molecular Weight: 214.3
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 402587-14-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Refractive Index: n20/D 1.462
• CAS DataBase Reference: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE(402587-14-8)
• EPA Substance Registry System: (+)-ETHYL (S)-2-HYDROXY-4-CYCLOHEXYLBUTYRATE(402587-14-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 402587-14-8(Hazardous Substances Data)

Upstream product

• 17851-38-6 ethyl 4-cyclohexylbutanoate 
• 125639-64-7 (S)-ethyl 2-hydroxy-4-phenylbutyrate 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 243658-52-8 (2S)-2-hydroxy-4-oxo-4-phenyl-butyric acid ethyl ester 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 244277-48-3 ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate 

Relevant articles and documents

Ethyl 2,4-dioxo-4-phenylbutyrate: A versatile intermediate for the large-scale preparation of enantiomerically pure α-hydroxy and α-amino acid esters

Starting from ethyl 2,4-dioxo-4-phenylbutyrate, both enantiomers of six enantiomerically pure α-hydroxy and α-amino acid esters (homophenylalanine derivatives) were prepared on >100 g scale. The key step involves a Pt-cinchona catalyzed enantioselective hydrogenation followed by enrichment via crystallization. All derivatives are commercially available.

BrF3, an underutilized reagent in organic chemistry: A novel C-C-N to C-N-C rearrangement

Little is known about bromine trifluoride in organic chemistry. Under the right conditions, it can be a useful tool and generate a new and unprecedented chemistry. Thus, when reacted with oxime methyl ethers of α-ketoesters, BrF3 was able to convert the oxime group into a CF2 group and through a new type of rearrangement cause a shift of the carboxylate group to the nitrogen atom. The novel structure of the α,α-difluorocarbamate was also proven by 15N NMR as demonstrated for compounds 3, 8, 9, 12, 15, and 18. Another novel "double rearrangement" was observed during the formation of 19. Dynamic 19F NMR experiments indicate a high nitrogen inversion-rotation (NIR) barrier for these novel carbamates of about 12.5 kcal/mol.