76671-57-3

Basic information

• Product Name: Propanoic acid, 2-phenoxy-, ethyl ester, (S)-
• CAS NO: 76671-57-3
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Mol File: 76671-57-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Propanoic acid, 2-phenoxy-, ethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2-phenoxy-, ethyl ester, (S)-(76671-57-3)
• EPA Substance Registry System: Propanoic acid, 2-phenoxy-, ethyl ester, (S)-(76671-57-3)

Safety Data

• Hazardous Substances Data: 76671-57-3(Hazardous Substances Data)

Upstream product

• 687-47-8 (S)-Ethyl lactate 
• 108-95-2 phenol 
• 6111-99-5 ethyl diazoalaninate 
• 42412-84-0 ethyl 2-phenoxypropionate 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 51063-99-1 (R)-ethyl 2-bromopropanoate 
• 3229-70-7 phenolate 
• 535-11-5 Ethyl 2-bromopropionate 

Downstream Products

• 87860-35-3 (S)-2-Methyl-2-phenoxy carbinolcid 
• 158109-37-6 (S)-2-phenoxypropyl toluene-4-sulfonate 
• 97534-38-8 (S)-2-phenoxypropyl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate 

Relevant articles and documents

Planar chiral [2.2]paracyclophane-based bisoxazoline ligands: Design, synthesis, and use in cu-catalyzed inter- and intramolecular asymmetric O-H insertion reactions

Centrally chiral bisoxazolines connected directly to a planar chiral [2.2]paracyclophane backbone were synthesized and evaluated as asymmetric ligands in Cu-catalyzed intermolecular ethanolic O-H insertion reactions of α-diazo esters. The reactivities and enantioselectivities of Cu complexes of the synthesized bisoxazoline ligands were lower than those of ligands without central chirality. However, planar chiral [2.2] paracyclophane-based bisoxazoline ligands with an inserted benzene spacer that had a sterically demanding isopropyl substituent showed good enantioselectivities in inter- and intramolecular aromatic O-H insertion reactions, without the aid of central chirality.

Asymmetric O–H insertion reaction of carbenoids catalyzed by chiral bicyclo bisoxazoline copper(I) and (II) complexes

Chiral copper(I) and (II)-bicyclobisoxazoline complexes were found to catalyze the insertion of α-diazocarbonyl compounds into O–H bonds of alcohols. The insertion reactions of various α-diazopropionates proceeded with moderate yields (40–90%) and high enantioselectivities (up to 92% and 94% with copper(I) and copper(II)-catalysts, respectively). A predominant effect on the enantiocontrol of the reaction was observed when copper(I) and (II)-catalysts were associated with NaBARF and molecular sieves (4??).

Resolution of (R, S)-ethyl-2-(4-hydroxyphenoxy) propanoate using lyophilized mycelium of Aspergillus oryzae WZ007

The mycelium of Aspergillus oryzae WZ007 was successfully developed to kinetic resolution of (R, S)-ethyl-2-(4-hydroxyphenoxy) propanoate ((R, S)-EHPP) for production of (R)-ethyl-2-(4-hydroxyphenoxy) propanoate ((R)-EHPP). The key biocatalytic process parameters (pH, temperature, rotation speed and substrate concentration) were optimized. Under the optimum conditions, the optical purity of (R)-EHPP was improved up to >99% when the conversion was above 49%. A. oryzae WZ007 whole-cell lipase exhibited high reaction capacity, enantioselectivity and good reusability. The tolerable substrate concentration was 0.5 mol/L, and dry mycelium of A. oryzae WZ007 maintains over 80% of its initial activity after eight repeating cycles. Therefore the enzymatic preparation of (R)-EHPP route was suitable for industrial application.