172585-57-8

Basic information

• Product Name: (R)-acetic acid 1-(4-fluoro-phenyl)-ethyl ester
• Synonyms: (R)-acetic acid 1-(4-fluoro-phenyl)-ethyl ester
• CAS NO: 172585-57-8
• Molecular Weight: 182.195
• Mol File: 172585-57-8.mol
• Article Data: 27

Chemical Properties

• CAS DataBase Reference: (R)-acetic acid 1-(4-fluoro-phenyl)-ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-acetic acid 1-(4-fluoro-phenyl)-ethyl ester(172585-57-8)
• EPA Substance Registry System: (R)-acetic acid 1-(4-fluoro-phenyl)-ethyl ester(172585-57-8)

Safety Data

• Hazardous Substances Data: 172585-57-8(Hazardous Substances Data)

Upstream product

• 108-22-5 Isopropenyl acetate 
• 403-41-8 1-(4-Fluorophenyl)ethanol 
• 108-24-7 acetic anhydride 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 147164-48-5 1-(4-fluorophenyl)ethenyl acetate 
• 108-05-4 vinyl acetate 
• 459-57-4 4-fluorobenzaldehyde 
• 403-41-8 (R)-1-(4-fluorophenyl)ethan-1-ol 
• 108-58-7 Resorcinol diacetate 
• 876-27-7 4-chlorophenyl acetate 
• 141-78-6 ethyl acetate 

Downstream Products

• 403-41-8 (R)-1-(4-fluorophenyl)ethan-1-ol 

Relevant articles and documents

Base-Free Dynamic Kinetic Resolution of Secondary Alcohols with a Ruthenium-Lipase Couple

We report the dynamic kinetic resolution (DKR) of various secondary alcohols by the combination of a ruthenium catalyst and an anionic surfactant-activated lipoprotein lipase. The DKR reactions performed under totally base-free conditions at room temperature provided the products of excellent enantiopurities (91-99% ee or greater) in high yields (92-99%). More importantly, the DKR of α-arylallyl alcohols was achieved for the first time with high yields (87-91%).

Synthesis and biological evaluation of disubstituted pyrimidines as selective 5-HT2C agonists

Here, we describe the synthesis of disubstituted pyrimidine derivatives and their biological evaluation as selective 5-HT2C agonists. To improve selectivity for 5-HT2C over other subtypes, we synthesized two series of disubstituted pyrimidines with fluorophenylalkoxy groups at either the 5-position or 4-position and varying cyclic amines at the 2-position. The in vitro cell-based assay and binding assay identified compounds 10a and 10f as potent 5-HT2C agonists. Further studies on selectivity to 5-HT subtypes and drug-like properties indicated that 2,4-disubstituted pyrimidine 10a showed a highly agonistic effect on the 5-HT2C receptor, with excellent selectivity, as well as exceptional drug-like properties, including high plasma and microsomal stability, along with low CYP inhibition. Thus, pyrimidine 10a could be considered a viable lead compound as a 5-HT2C selective agonist.

Accessing N-Stereogenicity through a Double Aza-Michael Reaction: Mechanistic Insights

Further development of the chemistry and applications of chiral compounds that possess configurationally stable stereogenic nitrogen atoms is hampered by the lack of efficient strategies to access such compounds in an enantiomerically pure form. Esters of propiolic acid and chiral alcohols were evaluated as cheap and readily available Michael acceptors in a diastereoselective synthesis of N-stereogenic compounds by means of a double aza-Michael conjugate addition. Diastereomeric ratios of up to 74:26 and high yields were achieved with (-)-menthyl propiolate as a substrate. Furthermore, a detailed mechanistic investigation was undertaken to shed some light on the course of this domino transformation. Kinetic studies revealed that the protic-solvent additive acts as a Bronsted acid and activates the ester toward the initial attack of the tetrahydrodiazocine partner. Conversely, acidic conditions proved unfavorable during the final cyclization step that provides the product.