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53066-16-3

53066-16-3

Identification

Synonyms:rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

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Relevant articles and documentsAll total 3 Articles be found

Lipase mediated enzymatic kinetic resolution of phenylethyl halohydrins acetates: A case of study and rationalization

Fonseca, Thiago de Sousa,Vega, Kimberly Benedetti,da Silva, Marcos Reinaldo,de Oliveira, Maria da Concei??o Ferreira,de Lemos, Telma Leda Gomes,Contente, Martina Letizia,Molinari, Francesco,Cespugli, Marco,Fortuna, Sara,Gardossi, Lucia,de Mattos, Marcos Carlos

, (2020/02/18)

Racemic phenylethyl halohydrins acetates containing several groups attached to the aromatic ring were resolved via hydrolysis reaction in the presence of lipase B from Candida antarctica (Novozym 435). In all cases, the kinetic resolution was highly selective (E > 200) leading to the corresponding (S)-β-halohydrin with ee > 99 %. However, the time required for an ideal 50 % conversion ranged from 15 min for 2,4-dichlorophenyl chlorohydrin acetate to 216 h for 2-chlorophenyl bromohydrin acetate. Six chlorohydrins and five bromohydrins were evaluated, the latter being less reactive. For the β-brominated substrates, steric hindrance on the aromatic ring played a crucial role, which was not observed for the β-chlorinated derivatives. To shed light on the different reaction rates, docking studies were carried out with all the substrates using MD simulations. The computational data obtained for the β-brominated substrates, based on the parameters analysed such as NAC (near attack conformation), distance between Ser-O and carbonyl-C and oxyanion site stabilization were in agreement with the experimental results. On the other hand, the data obtained for β-chlorinated substrates suggested that physical aspects such as high hydrophobicity or induced change in the conformation of the enzymatic active site are more relevant aspects when compared to steric hindrance effects.

Chemoenzymatic Synthesis of Luliconazole Mediated by Lipases

Fonseca, Thiago de S.,Lima, Lara D.,de Oliveira, Maria da C. F.,de Lemos, Telma L. G.,Zampieri, Davila,Molinari, Francesco,de Mattos, Marcos C.

, p. 2110 - 2116 (2018/05/31)

A straightforward chemoenzymatic synthesis of luliconazole has been developed. The key step involved the preparation of the enantiomerically pure β-halohydrin (1S)-2-chloro-1-(2,4-dichlorophenyl)-1-ethanol through kinetic resolution of the corresponding racemic acetate. This was achieved by a hydrolytic approach, mediated by the lipase from Thermomyces lanuginosus or Novozym 435. The latter enzyme proved to be a robust biocatalyst for the kinetic resolution, and the (S)-β-halohydrin was obtained with high selectivity (ee > 99 %, E > 200) after just 15 min, at 45 °C. It could be reused five times with maintenance of high values of both conversion and enantioselectivity. Subsequently, the (S)-β-halohydrin was subjected to a mesylation reaction; the mesylated derivative reacted with 1-cyanomethylimidazole in the presence of CS2 to give luliconazole in 43 % yield with >99 % ee.

Asymmetric chemoenzymatic synthesis of miconazole and econazole enantiomers. the importance of chirality in their biological evaluation

Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Malpartida, Francisco,Gotor, Vicente

, p. 2115 - 2122 (2011/05/19)

A simple and novel chemoenzymatic route has been applied for the first time in the synthesis of miconazole and econazole single enantiomers. Lipases and oxidoreductases have been tested in stereoselective processes; the best results were attained with oxidoreductases for the introduction of chirality in an adequate intermediate. The behaviors of a series of ketones and racemic alcohols in bioreductions and acetylation procedures, respectively, have been investigated; the best results were found with alcohol dehydrogenases A and T, which allowed the production of (R)-2-chloro-1-(2,4-dichlorophenyl)ethanol in enantiopure form under very mild reaction conditions. Final chemical modifications have been performed in order to isolate the target fungicides miconazole and econazole both as racemates and as single enantiomers. Biological evaluation of the racemates and single enantiomers has shown remarkable differences against the growth of several microorganisms; while (R)-miconazole seemed to account for most of the biological activity of racemic miconazole on all the strains tested, both enantiomers of econazole showed considerable biological activities. In this manner, (R)-econazole showed higher values against Candida krusei, while higher values were observed for (S)-econazole against Cryptococcus neoformans, Penicillium chrysogenum, and Aspergillus niger.

Process route upstream and downstream products

Process route

α-(chloromethyl)-2,4-dichlorobenzyl alcohol
13692-14-3,114446-57-0

α-(chloromethyl)-2,4-dichlorobenzyl alcohol

acetic anhydride
108-24-7

acetic anhydride

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

Conditions
Conditions Yield
With dmap; triethylamine; In dichloromethane; for 3h; Inert atmosphere;
96%
With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;
91%
With dmap; In dichloromethane; at 20 ℃; for 2h;
91%
2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
2: dmap; triethylamine / dichloromethane / 3 h / Inert atmosphere
With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C
2: dmap; triethylamine / dichloromethane / 2 h / 20 °C
With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C
2: dmap / dichloromethane / 2 h / 20 °C
With dmap; sodium tetrahydroborate; In methanol; dichloromethane;
rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

(S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol
114446-57-0

(S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol

2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

Conditions
Conditions Yield
With candida antarctica lipase type B immobilized on acrylic resin; In aq. phosphate buffer; at 45 ℃; for 0.25h; pH=7; Reagent/catalyst; Temperature; Time; enantioselective reaction; Catalytic behavior; Resolution of racemate; Enzymatic reaction;
46.5%
44.5%
With Candida antarctica lipase B; In aq. phosphate buffer; at 45 ℃; for 0.25h; pH=7; enantioselective reaction; Enzymatic reaction;
> 99 % ee
rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

(S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol
114446-57-0

(S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol

2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

chloro-1-(2,4-dichlorophenyl)ethyl acetate

chloro-1-(2,4-dichlorophenyl)ethyl acetate

Conditions
Conditions Yield
With thermomyces lanuginosus lipase immobilized on immobead-150; In aq. phosphate buffer; at 45 ℃; for 0.25h; pH=7; Reagent/catalyst; enantioselective reaction; Resolution of racemate; Enzymatic reaction;
41 % ee
> 99 % ee
rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

(S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol
114446-57-0

(S)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol

(R)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol
114446-57-0

(R)-2-chloro-1-(2',4'-dichlorophenyl)-1-ethanol

2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

chloro-1-(2,4-dichlorophenyl)ethyl acetate

chloro-1-(2,4-dichlorophenyl)ethyl acetate

Conditions
Conditions Yield
With amano PS from burkholderia cepacia immobilized on diatomaceous earth; In aq. phosphate buffer; at 30 ℃; for 19h; pH=7; Reagent/catalyst; enantioselective reaction; Resolution of racemate;
80 % ee
74 % ee
rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile
187164-19-8

[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile

luliconazole
187164-19-8

luliconazole

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: candida antarctica lipase type B immobilized on acrylic resin / aq. phosphate buffer / 0.25 h / 45 °C / pH 7 / Resolution of racemate; Enzymatic reaction
2.1: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
3.1: potassium hydroxide / dimethyl sulfoxide / 2 h / 4 - 20 °C
3.2: 24 h / 4 - 20 °C
With dmap; candida antarctica lipase type B immobilized on acrylic resin; triethylamine; potassium hydroxide; In aq. phosphate buffer; dichloromethane; dimethyl sulfoxide;
Multi-step reaction with 3 steps
1.1: thermomyces lanuginosus lipase immobilized on immobead-150 / aq. phosphate buffer / 0.25 h / 45 °C / pH 7 / Resolution of racemate; Enzymatic reaction
2.1: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
3.1: potassium hydroxide / dimethyl sulfoxide / 2 h / 4 - 20 °C
3.2: 24 h / 4 - 20 °C
With dmap; thermomyces lanuginosus lipase immobilized on immobead-150; triethylamine; potassium hydroxide; In aq. phosphate buffer; dichloromethane; dimethyl sulfoxide;
rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate
53066-16-3

rac-2-chloro-1-(2,4-dichlorophenyl)ethyl acetate

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate
229334-55-8

(S)-2-chloro-1-(2,4-dichlorophenyl)ethyl methanesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: candida antarctica lipase type B immobilized on acrylic resin / aq. phosphate buffer / 0.25 h / 45 °C / pH 7 / Resolution of racemate; Enzymatic reaction
2: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C
With dmap; candida antarctica lipase type B immobilized on acrylic resin; triethylamine; In aq. phosphate buffer; dichloromethane;

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  • Finetech Industry Limited
  • Business Type:Trading Company
  • Contact Tel:86-27-87465837
  • Emails:sales@finetechnology-ind.com
  • Main Products:29
  • Country:China (Mainland)
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