57573-90-7

Upstream product

• 108-22-5 Isopropenyl acetate 
• 57605-95-5 1-(1-naphthyl)ethanol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 
• 876-27-7 4-chlorophenyl acetate 
• 54519-07-2 vinyl ester of 3-phenylpropionic acid 
• 941-98-0 1'-naphthacetophenone 

Downstream Products

• 42177-25-3 (R)-1-(naphth-1-yl)ethanol 
• 16197-94-7 (S)-(-)-1-(naphthalen-1-yl)ethyl acetate 
• 16197-95-8 1-(naphthalen-1-yl)ethyl acetate 
• 57605-95-5 1-(1-naphthyl)ethanol 
• 941-98-0 1'-naphthacetophenone 
• 15914-84-8 (S)-1-(1-Naphthyl)ethanol 

Relevant academic research and scientific papers

PQXdpap: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols

Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-(dipropylamino)pyridin-3-yl pendants at the 5-position of the quinoxaline ring (PQXdpap) exhibited high catalytic activities and moderate to high selectivities (up to s = 87) in the acylative kinetic resolution of secondary alcohols. The solvent-dependent helical chirality switching of PQXdpap between pure toluene and a 1:1 mixture of toluene and 1,1,2-trichloroethane enabled the preparation of either compound of a pair of enantiomerically pure alcohols (>99% ee) from a single catalyst.

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.

Chemical-enzyme method used for synthesis of cinacalcet

The invention discloses a chemical-enzyme method used for synthesis of cinacalcet. The chemical-enzyme method cmprises following steps: under catalyst effect of lipase, racemic 1-(1-naphthyl)ethanol and a fatty acid vinyl ester are subjected to kinetic resolution in a solvent so as to obtain (S)-1-(1-naphthyl) ethanol; under the effect of a catalyst, (S)-1-(1-naphthyl) ethanol and 3-(3-(trifluoromethyl)phenyl)propylamine are subjected to Mitsunobu reaction so as to obtain cinacalcet. According to the chemical-enzyme method, racemic 1-(1-naphthyl)ethanol is taken as an initial raw material, biological enzyme resolution is adopted so as to obtain (S)-1-(1-naphthyl) ethanol, and (S)-1-(1-naphthyl) ethanol and 3-(3-(trifluoromethyl)phenyl)propylamine are subjected to Mitsunobu reaction so asto obtain cinacalcet. Compared with the prior art, the advantages are that: reaction steps are few; operation is simple; no high pressure container is used for hydrogenation reduction; no expensive reducing agent is used; reaction conditions are mild; safety is high; the yield and purity are high; and the purity is as high as 99% or higher.

Remarkably improved stability and enhanced activity of a: Burkholderia cepacia lipase by coating with a triazolium alkyl-PEG sulfate ionic liquid

Three types of triazolium cetyl-PEG10 sulfate ionic liquid were synthesized and their activation of Burkholderia cepacia lipase was investigated; both the reaction rate and enantioselectivity depended on the cationic part of the coating ILs and 1-butyl-3-methyl-1,2,3-triazolium cetyl-PEG10 sulfate (Tz1)-coated lipase PS, which is especially suitable for the transesterification of 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, and 1-(pyridin-4-yl)ethanol, among 12 types of tested secondary alcohol. The most important result was obtained when these enzymes were stored in an IL ([N221MEM][Tf2N]) solvent: Tz1-PS showed an amazing stability and it exhibited an excellent activity after 2 years when the enzyme was stored in [N221MEM][Tf2N].

Mechanochemical Enzymatic Kinetic Resolution of Secondary Alcohols under Ball-Milling Conditions

Mechanosynthesis is a valuable technique, offering attractive alternatives for the preparation of organic, inorganic, and organometallic products. Surprisingly, mechanochemical enzymatic transformations have only scarcely been studied until now. Here, we demonstrate the use of lipase B from Candida antarctica (CALB) in acylative kinetic resolutions of secondary alcohols in mixer and planetary mills. Despite the mechanical stress caused by the high-speed ball milling, the biocatalyst proved highly effective, stable, and, in part, recyclable under the applied mechanochemical conditions. Best milling practice: The compatibility of lipase B from Candida antarctica (CALB) in acylative kinetic resolutions of secondary alcohols in mixer and planetary mills has been explored. Despite the mechanical stress caused by the high-speed ball milling, the biocatalyst was found to be very effective, stable, and, in part, recyclable under the applied mechanochemical conditions.

A green route to enantioenriched (S)-arylalkyl carbinols by deracemization via combined lipase alkaline-hydrolysis/Mitsunobu esterification

Herein we report results of the chemoenzymatic deracemization of a range of secondary benzylic acetates 1a-9a via a sequence of hydrolysis with CAL-B lipase in non-conventional media, combined with esterification of the recovered alcohol according to the Mitsunobu protocol following an enzymatic kinetic resolution (KR). The KR of racemic acetates 1a-9a via an enzymatic hydrolysis, with CAL-B lipase and Na2CO3, in non-aqueous media was optimized and gave high selectivities (E ? 200) at good conversions (C >49%) for all of the substrates studied. This method competes well with the traditional one performed in a phosphate buffer solution. The deracemization using Mitsunobu inversion gave the (S)-acetates in moderate to excellent enantiomeric excess 75% ee 99%, in acceptable isolated yields 70% yield 89%, and with some variations according to the acetate structure.

Kinetic resolution of secondary alcohols by chiral dmap derivatives prepared by the Ugi multicomponent reaction

The kinetic resolution of secondary alcohols was examined by new chiral DMAP derivatives, which can readily be prepared by the Ugi multicomponent reaction in a one-pot operation. The initial screening of DMAP derivatives indicated that the catalyst bearing L-valine with an S configuration at the a-position of amide showed the best stereoselectivity factor. After the reaction conditions were optimized with (S,S)-4a in the kinetic resolution of secondary alcohols, various acyclic and cyclic secondary alcohols could be resolved with an s -factor of up to 12.

Kinetic resolution of secondary alcohols by the combination of a chiral Br?nsted acid, DABCO, and acetyl chloride

An efficient and simple protocol for the kinetic resolution of secondary alcohols is presented. The new system is based on a combination of chiral Br?nsted acid, DABCO, and acetyl chloride and gives various enantioenriched alcohols with selectivity factors up to 105.

Lipase catalyzed kinetic resolution of (±)-1-(1-naphthyl) ethanol under microwave irradiation

1-(1-Naphthyl) ethanol is an important chiral building block for the synthesis of active pharmaceutical intermediates (APIs). In this work, lipase catalyzed kinetic resolution of (RS)-1-(1-naphthyl) ethanol via transesterification was studied under microwave irradiation with different acyl donors. Vinyl acetate was the most effective and hence used as the acyl donor. Three different commercially available immobilized lipases were used, among which Candida antarctica lipase B, immobilized on acrylic resin (Novozym 435) was found to be the best catalyst in n-heptane as solvent. The effect of various parameters was studied in a systematic manner. The reaction was intrinsically kinetically controlled. Maximum conversion of 47.74% with enantiometric excess of substrate (ees) of 90.05% and enantiomeric ratio (E) of 433.39 was obtained in 3 h using 30 mg of enzyme loading with equi-molar ratio of alcohol to ester at 60°C. From the progress curve analysis, the ping-pong bi-bi mechanism with inhibition by both substrates was found to fit the initial rates. Kinetic parameters were obtained by using non-linear regression. The process is efficient and easily scalable as compared to the chemical process.

Lipase-catalysed kinetic resolutions of secondary alcohols in pressurised liquid hydrofluorocarbons

Three model secondary alcohols have been subjected to enzymatic kinetic resolution using three common lipases and a typical acyl donor. The resolutions were performed in two pressurised low-boiling hydrofluorocarbons, which are novel media for enzymatic reactions, and five conventional organic solvents. In general, higher yields, ee's and rates of reaction were observed in the hydrofluorocarbons.