66513-22-2

Upstream product

• 687-47-8 (S)-Ethyl lactate 
• 1570-64-5 2-methyl-4-chlorophenol 
• 57057-80-4 ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate 

Downstream Products

• 16484-77-8 (R)-Mecoprop 
• 66423-13-0 (R)-2-(4-chloro-2-methylphenoxy)propionic acid octyl ester 

Relevant academic research and scientific papers

Design, Synthesis, and Pharmacological Evaluation of Novel β2/3 Subunit-Selective γ-Aminobutyric Acid Type A (GABAA) Receptor Modulators

Subunit-selective modulation of γ-aminobutyric acid type A receptors (GABAAR) is considered to exert fewer side effects compared to unselective clinically used drugs. Here, the β2/3 subunit-selective GABAAR modulators valerenic acid (VA) and loreclezole (LOR) guided the synthesis of novel subunit-selective ligands with simplified structures. We studied their effects on GABAARs expressed in Xenopus laevis oocytes using two-microelectrode voltage clamp technique. Five compounds showed significantly more efficacious modulation of GABA-evoked currents than VA and LOR with retained potency and selectivity. Compound 18 [(E)-2-Cyano-3-(2,4-dichlorophenyl)but-2-enamide] induced the highest maximal modulation of GABA-induced chloride currents (Emax: 3114 ± 242%), while 12 [(Z)-3-(2,4-dichlorophenyl)but-2-enenitrile] displayed the highest potency (EC50: 13 ± 2 μM). Furthermore, in hippocampal neurons 12 facilitated phasic and tonic GABAergic inhibition, and in vivo studies revealed significantly more potent protection against pentylenetetrazole (PTZ)-induced seizures compared to VA and LOR. Collectively, compound 12 constitutes a novel, simplified, and subunit-selective GABAAR modulator with low-dose anticonvulsant activity.

Industrial production improvement process for (R)-2-(4-chlorine-2-methyl phenoxy) octyl propionate root retarder

The invention discloses an industrial production improvement process for a (R)-2-(4-chlorine-2-methyl phenoxy) octyl propionate root retarder which can be used as a root retarder. The production process is characterized by comprising the following steps: by taking methylbenzene as a solvent, triethylamine as an acid-binding agent, and pyridine as a catalyst, carrying out sulfonation on L-ethyl lactate and paratoluensulfonyl chloride so as to obtain a corresponding sulfonyl ester intermediate product; under the promotion of sodium hydroxide, carrying out etherification on the sulfonyl ester intermediate product with 4-chlorine o-cresol so as to obtain an aromatic ester ether compound; at a certain temperature and pressure, carrying out ester exchange on the ester ether compound with n-octylalcohol, thereby obtaining the (R)-2-(4-chlorine-2-methyl phenoxy) octyl propionate. The (R)-2-(4-chlorine-2-methyl phenoxy) octyl propionate prepared by using the production improvement process disclosed by the invention is high in optical content, small in raw material optical loss and high in yield, and can be directly applied to process production of root puncturing resistant waterproof rolls. The production process has large application prospects.

Preparation method of octyl (R)-2-(4-chloro-2-methylphenoxy) propionate root retarder

The invention discloses a preparation method of octyl (R)-2-(4-chloro-2-methylphenoxy) propionate which can be used as a root retarder. The preparation method comprises the following steps: with ethyl L-lactate as a raw material, sulfonating together with p-toluenesulfonyl chloride to obtain a corresponding sulfonyl ester compound; etherifying the sulfonyl ester compound and 4-chloro-o-cresol to obtain a corresponding aromatic ether ester compound; and finally, performing transesterification on the ether ester compound and n-octyl alcohol to obtain octyl (R)-2-(4-chloro-2-methylphenoxy) propionate. Octyl (R)-2-(4-chloro-2-methylphenoxy) propionate prepared by the preparation method provided by the invention is high in optical content, relatively small in optical loss of raw materials and relatively high in yield. The invention establishes a reaction system with the characteristics of simple preparation process, mild reaction condition and low cost, so that the problems that the compound is imported and has a scarce source are solved to a certain extent.

Rapid and efficient synthesis of (R)-aryloxypropionic acid esters under microwave irradiation

A series of (R)-(+)-ethyl aryloxypropionates (4a-4p) have been synthesized by the reaction of substituted phenols with ethyl (S)-(-)-tosyloxy lactate under the conditions of microwave irradiation and without solvents. The reaction conditions have been optimized. A good method for the preparation of (R)-(+)-ethyl aryloxypropionate was developed, with good yields, high enantiomer excess, short reaction times, easy workup, and simple procedure. Copyright Taylor & Francis Group, LLC.

PROCESS FOR PREPARING (R)-ARYLOXYPROPIONIC ACID ESTER DERIVATIVES

The present invention relates to a method for preparing optically active (R)-aryloxypropionic acid ester derivatives, and more particularly to a method for preparing (R)- aryloxypropionic acid ester derivatives with high optical purity and good yield at low cost from phenol derivatives with various substituted functional groups and (S)-alkyl O-arylsulfonyl lactates.

Carboxylic acids and skeletal muscle chloride channel conductance: Effects on the biological activity induced by the introduction of methyl groups on the aromatic ring of chiral α-(4-chloro-phenoxy)alkanoic acids

One or two methyl groups have been introduced on the aromatic ring of two chiral clofibric acid analogs, 2-(4-chloro-phenoxy)propanoic and 2-(4-chloro-phenoxy)butanoic acids. The biological activity of the derivatives obtained (3-6) has been evaluated on the skeletal muscle chloride conductance (gCl). The results confirm the hypothesis of two different sites modulating chloride channel function, an excitatory site that increases channel activity and an inhibitory site that produces a channel block. In fact, this chemical modification strongly reduces the blocking activity of the (R)-and (S)-enantiomers in comparison with the parent compounds, but does not markedly affect the ability of the (R)-enantiomers to increase chloride channel conductance.