103665-43-6

Basic information

• Product Name: (S)-1-acetoxy-1-phenyl-2-chloroethane
• Synonyms: (S)-1-acetoxy-1-phenyl-2-chloroethane
• CAS NO: 103665-43-6
• Molecular Weight: 198.649
• Mol File: 103665-43-6.mol

Chemical Properties

• CAS DataBase Reference: (S)-1-acetoxy-1-phenyl-2-chloroethane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-acetoxy-1-phenyl-2-chloroethane(103665-43-6)
• EPA Substance Registry System: (S)-1-acetoxy-1-phenyl-2-chloroethane(103665-43-6)

Safety Data

• Hazardous Substances Data: 103665-43-6(Hazardous Substances Data)

Upstream product

• 63318-61-6 α-Aethoxyacrylsaeuremethylester 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 108-22-5 Isopropenyl acetate 
• 532-27-4 1-chloroacetophenone 
• 108-05-4 vinyl acetate 
• 108-24-7 acetic anhydride 
• 70111-05-6 (S)-2-chloro-1-phenylethanol 
• 876-27-7 4-chlorophenyl acetate 
• 5177-66-2 1-ethoxyvinyl acetate 
• 75-36-5 acetyl chloride 

Downstream Products

• 20780-54-5 (S)-styrene oxide 

Relevant articles and documents

Synthesis of chiral aromatic alcohols: Use of new C2-symmetric RhIIICp*, RuII(cymene), or RuII(benzene) complexes containing chiral diaminocyclohexane ligand as asymmetric transfer hydrogenation catalyst

Twelve chiral secondary alcohols were synthesized by asymmetric transfer hydrogenation (ATH) using C2-symmetric bis(sulfonamide) ligand (2) derived from (1R,2R)-cyclohexane-1,2-diamine and complexed with [RhCl 2CP*]2, [RuCl2(cymene)] 2, or [RuCl2(benzene)]2 and then used in situ in the reduction of prochiral ketones. The alcohols were obtained in 85-99% yield and 90-99% enantioselectivity with isopropanol as the hydrogen source. Two-fold rate enhancement and better yields were achieved (88-99%) with 80-99% enantioselectivity using the complex [RhCl2CP*] 2 and aqueous sodium formate as the hydrogen source.

A Cationic Ruthenium Complex for the Dynamic Kinetic Resolution of Secondary Alcohols

A synthetic protocol making use of a well-defined cationic ruthenium complex 2 enabling the racemization of enantiomerically pure secondary alcohols in the presence of a weak base (K2CO3) is described. The compatibility of 2 with Candida Antarctica lipase B (Novozym 435) allows the development of an efficient dynamic kinetic resolution of sec-alcohols in the absence of an additional strong base. This procedure involves the first example of a dynamic kinetic resolution of alcohols in the presence of a cationic ruthenium catalyst. In addition, we describe the conversion of ketones to the enantioenriched acetates in a one-pot reaction, probing the versatility of complex 2.

1-Ethoxyvinyl acetate as a novel, highly reactive, and reliable acyl donor for enzymatic resolution of alcohols

1-Ethoxyvinyl acetate 3 was found to be a high performance acyl donor for enzymatic resolution of alcohols featuring that (i) 3 shows high reactivity and high selectivity comparable to the most widely used vinyl acetate 1 and (ii) reaction of 3 generates low reactivity ethyl acetate 6 as a single side product, while that of 1 releases unfavorable acetaldehyde 4.

Biocatalysis in Ionic Liquids: Markedly Enhanced Enantioselectivity of Lipase

matrix presented Lipase-catalyzed transesterifications in ionic liquids proceeded with markedly enhanced enantioselectivity. It was observed that lipases were up to 25 times more enantioselective in ionic liquids than in conventional organic solvents.

DMSO-triggered enhancement of enantioselectivity in Novozyme[435]-catalyzed transesterification of chiral 1-phenylethanols

Dimethyl sulfoxide as cosolvent enhances the enantioselectivity of resolved products up to 100% in the Novozyme[435]-catalyzed transesterification of chiral 1-phenylethanols but not 1-phenyl-2-haloethanols in THF. The reaction does not proceed in lipophilic and water-miscible polar solvents.

Enhanced activity and modified substrate-favoritism of Burkholderia cepacia lipase by the treatment with a pyridinium alkyl-PEG sulfate ionic liquid

Three types of pyridinium salts, i.e., 1-ethylpyridin-1-ium cetyl-PEG10 sulfate (PYET), 1-butylpyridin-1-ium cetyl-PEG10 sulfate (PYBU), and 1-(3-methoxypropyl)pyridin-1-ium cetyl-PEG10 sulfate (PYMP), have been prepared and evaluated for their activation property of Burkholderia cepacia lipase by comparison to the control IL-coated enzymes, 1-butyl-2,3-dimethylimidazolium cetyl-PEG10 sulfate-coated lipase PS (IL1-PS). Among the tested pyridinium salt-coated lipases, the PYET-coated lipase PS (PYET-PS) exhibited the best results; the transesterification of 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, 1-(pyridin-4-yl)ethanol, or 4-phenylbut-3-en-2-ol proceeded faster than those of the IL1-PS-catalyzed reaction while maintaining an excellent enantioselectivity (E > 200). This improved efficiency was found to be dependent on the increased Kcat value.

Immobilization of Amano lipase from Pseudomonas fluorescens on silk fibroin spheres: an alternative protocol for the enantioselective synthesis of halohydrins

The search for a new, efficient, cheaper and sustainable matrix for lipase immobilization is a growing area in biotechnology. Amano lipase from Pseudomonas fluorescens was immobilized on silk fibroin spheres and used in the enzymatic kinetic resolution of halohydrins, to obtain optically active epoxides (up to 99% ee), important precursors in the synthesis of derivative antifungal azoles. This paper reinforces the versatility of silk fibroin as a support for heterogeneous catalysts.

Synthetically useful variants of industrial lipases from: Burkholderia cepacia and Pseudomonas fluorescens

Industrial enzymes lipase PS (LPS) and lipase AK (LAK), which originate from Burkholderia cepacia and Pseudomonas fluorescens, respectively, are synthetically useful biocatalysts. To strengthen their catalytic performances, we introduced two mutations into hot spots of the active sites (residues 287 and 290). The LPS-L287F/I290A double mutant showed high catalytic activity and enantioselectivity for poor substrates for which the wild-type enzyme showed very low activity. The LAK-V287F/I290A double mutant was also an excellent biocatalyst with expanded substrate scope, which was comparable to the LPS-L287F/I290A double mutant. Thermodynamic parameters were determined to address the origin of the high enantioselectivity of the double mutant. The ΔΔH? term, but not the ΔΔS? term, was predominant, which suggests that the enantioselectivity is driven by a differential energy associated with intermolecular interactions around Phe287 and Ala290. A remarkable solvent effect was observed, giving a bell-shaped profile between the E values and the log&P or ? values of solvents with the highest E value in i-Pr2O. This suggests that an organic solvent with appropriate hydrophobicity and polarity provides the double mutant with some flexibility that is essential for excellent catalytic performance.

Highly enantioselective acylation of chlorohydrins using Amano AK lipase from P. fluorescens immobilized on silk fibroin-alginate spheres

Aromatic, allylic, and aliphatic compounds containing a chlorohydrin group were selected as substrates for the enzymatic kinetic resolution mediated by Amano AK lipase from Pseudomonas fluorescens immobilized in silk friboin-alginate spheres. Thus, the en

Asymmetric transfer hydrogenation of ketones in aqueous solution catalyzed by rhodium(III) complexes with C2-symmetric fluorene-ligands containing chiral (1R,2R)-cyclohexane-1,2-diamine

Two C2-symmetric bis(sulfonamide) ligands containing fluorene-chiral (1R,2R)-cyclohexane- 1,2-diamine were complexed to Rh III(Cp*) and used as catalyst to reduce aromatic ketones. The corresponding chiral secondary alcohols were obtained in 87-100percent ee and 85-99percent yield, under asymmetric transfer hydrogenation (ATH) conditions using aqueous sodium formate as the hydride source. With acetophenone, 94percent ee and 86-97percent yield was achieved with substrate/catalyst (S/C) ratio of 10,000.