122-35-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenoxypropionyl chloride is used as a reagent for the synthesis of pharmaceuticals, facilitating the production of various medicinal compounds. Its high reactivity allows for the formation of new chemical entities that can be used to treat a range of medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Phenoxypropionyl chloride is used as a reagent for the synthesis of agrochemicals, contributing to the development of products that enhance crop protection and increase agricultural yields. Its role in the synthesis process is crucial for creating effective and targeted agrochemicals.
Used in Organic Synthesis:
2-Phenoxypropionyl chloride is used as an intermediate in organic synthesis for the creation of a variety of chemical compounds. Its versatility in forming new compounds makes it a valuable component in the development of new materials and substances for various applications.

InChI:InChI=1/C9H9ClO2/c1-7(9(10)11)12-8-5-3-2-4-6-8/h2-7H,1H3

Upstream product

• 100-67-4 potassium phenolate 
• 139-02-6 sodium phenoxide 
• 108-95-2 phenol 
• 940-31-8 2-phenoxypropionic acid 

Downstream Products

• 87385-60-2 1-diazo-3-phenoxy-2-propanone 
• 92817-69-1 4'-methyl-2',6'-di-tert-butylphenyl (RS)-2-phenoxypropanoate 
• 446878-78-0 2-Phenoxypropionsaeureanhydrid 
• 107449-15-0 2-diazo-4-phenoxy-3-pentanone 
• 107299-98-9 cis-2,5-diphenyl-4-methyl-4-phenoxy-4,5-dihydropyrazolo<1,5-a>pyridine 
• 116871-94-4 5-Oxo-1-(2-phenoxy-propionyl)-pyrrolidine-2-carboxylic acid propyl ester 
• 2065-24-9 methyl 2-phenoxypropanoate 
• 166115-80-6 N-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-2-phenoxy-propionamide 
• 349088-40-0 1-(4-benzyl-piperazin-1-yl)-2-phenoxy-propan-1-one 
• 1912-23-8 (S)-2-phenoxypropanoic acid 
• 1177418-35-7 N-(4-[3-(4-fluorophenyl)-5-isopropylisoxazol-4-yl]pyridin-2-yl)-2-phenoxypropanamide 
• 1048953-70-3 N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)-2-phenoxypropanamide 
• 478932-13-7 N-[2-(4-hydroxyphenyl)ethyl]-2-(2-phenoxypropionylamino)acrylamide 
• 478932-12-6 2-(2-phenoxypropionylamino)acrylamide 

Relevant academic research and scientific papers

Synthesis process of 2-phenoxypropionyl chloride

The invention discloses a synthesis process of 2-phenoxypropionyl chloride. The synthesis process comprises the following steps: (1) under conditions of water and alkali, by taking phenol and 2-chloropropionic acid as raw materials, carrying out reaction, adding acid at the end of the reaction to adjust the pH till the solution is in a faintly acid state, and carrying out suction filtering to obtain 2-phenoxypropionic acid; (2) dissolving the 2-phenoxypropionic acid in an organic solvent, adding an acyl chlorinating agent for reaction, removing the organic solvent at the end of the reaction, and collecting a fraction with temperature of 80 DEG C, so as to obtain the 2-phenoxypropionyl chloride, wherein a mole ratio of the phenol to the 2-chloropropionic acid is 1 to 1.2-1.5; a mole ratio of the phenol and the alkali is 1 to 1.2-5.0; a mole ratio of solid powder a and the acyl chlorinating agent is 1 to 1.2-2.0. The method disclosed by the invention is easy to operate; selected reactionconditions are mild (0 to 80 DEG C); selected reagents are readily available; the amount of waste gas, wastewater and solid wastes is small; the synthesis process is environmentally friendly and lowin harm to a human body.

Mutual Kinetic Resolution of Racemic 3,4-Dihydro-3-methyl-2H-[1,4]benzoxazines with Acyl Chlorides of Racemic O-Phenyllactic Acids and DFT Modelling of Transition States

The effect of the electronic nature of the para substituent on the aromatic ring of 2-aryloxypropionyl chlorides on the stereochemical outcome of the acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its 7,8-difluoro-containing analogue has been studied. The geometries of the diastereoisomeric transition states and the corresponding Gibbs free enthalpies of activation were determined through DFT calculations at the COSMO-CH2Cl2-B3LYP-D3-gCP/def2-TZVP (or def2-SVP)//B3LYP-D3-gCP/def2-SVP level of theory. It has been found that a low-cost quantum chemical calculation at a chosen level of theory describes well the quantitative dependence of the selectivity of acylation on the structures of the reagents. The obtained results indicate that aromatic interactions between the reagents play a significant role in the process of stereodifferentiation, ensuring high selectivity of the acylation of benzoxazines with 2-aryloxyacyl chlorides.

Synthesis and Caco-2 cell permeability of N-substituted anthranilamide esters as ADP inhibitor in platelets

Twelve N-substituted anthranilamide esters (1-5, 8, 9, 12, 13, and 15-17) were synthesized and evaluated for their ability to inhibit the in vitro aggregation by washed human platelets induced by adenosine 5′-diphosphate (10 μM). The antiplatelet activity of DL-n-butyl 5-hydroxy-N-(2-phenoxypropionyl)anthranilate (9, IC50 = 10.5 μM) was most active among the tested compounds and ethyl ester 8 (IC50 = 11.2 μM) showed the second most activity. DL-Ethyl and DL-n-butyl 5-(p-toluenesulfonyloxy)-N-(2-phenoxypropionyl)anthranilate (12, IC50 = 13.1 μM and 13, IC50 = 14.0 μM), DL-methyl N-(2-phenoxybutyryl)anthranilate (2, IC50 = 12.7 μM), DL-N-(2-phenoxypropionyl)anthranilic acid (5, IC50 = 13.7 μM) displayed lower antiplatelet activity than 8 and 9. Compound 5 was more active than methyl ester prodrug 1. n-Butyl 5-hydroxy-N-(4′-acetoxybenzoyl)anthranilate (15, IC50 = 28.3 μM) showed moderate activity. Compounds 1 (IC50 = 42.8 μM), 4 (IC50 = 56.7 μM), 16 (IC50 = 51.0 μM), and 17 (IC50 = 49.8 μM) exhibited low antiplatelet activity. Methyl N-phenoxyacetylanthranilate (3, IC50 = 78.0 μM) showed the lowest antiplatelet activity. The compounds with branched alkyl chain (2 and 5) were more active than compounds with straight chain (3 and 4). The apparent permeability coefficient (Papp, cm/s) values of compounds 2 and 9 were determined as 45.34 ± 4.67 and 33.17 ± 5.15 × 10-6 cm/s by Caco-2 cell permeability assay.

Design, synthesis and structure-activity relationship studies of novel phenoxyacetamide-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1) has attracted extensive attention as a novel antidiabetic target in the last decade. Several FFA1 agonists reported in the literature have been suffered from relatively high molecular weight and lipophilicity. We have previously reported the FFA1 agonist 1. Based on the common amide structural characteristic of SAR1 and NIH screened compound, we here describe the continued structure-activity exploration to decrease the molecular weight and lipophilicity of the compound 1 series by converting various amide linkers. All of these efforts lead to the discovery of the preferable lead compound 18, a compound with considerable agonistic activity, high LE and LLE values, lower lipophilicity than previously reported agonists, and appreciable efficacy on glucose tolerance in both normal and type 2 diabetic mice.

Base-catalyzed bifunctional addition to amides and imides at low temperature. A new pathway for carbonyl hydrogenation

Mono- or dideprotonation at the N-H groups of the Noyori ketone hydrogenation catalyst trans-[RuH2((R)-BINAP)((R,R)-dpen)] (1a) yields trans-M[RuH2((R,R)-HNCH(Ph)CH(Ph)NH2)((R)-BINAP)], where M = K+(8-K) or Li+ (8-Li), or trans-M 2[RuH2((R,R)-HNCH(Ph)CH(Ph)NH)((R)-BINAP)], where M = Li+ (8-M′2), which have unprecedented activity toward the hydrogenation of amide and imide carbonyls at low temperatures in THF-d8. Details of the origins of the enantioselection for the desymmetrization of meso-cyclic imides by hydrogenation with 8-K are also described herein.

Investigation of solvolysis kinetics of new synthesized fluocinolone acetonide C-21 esters-an in vitro model for prodrug activation

In this study the solvolysis of newly synthesized fluocinolone acetonide C-21 esters was analysed in comparison with fluocinonide during a 24-hour period of time. The solvolysis was performed in an ethanol-water (90:10 v/v) mixture using the excess of NaHCO3. The solvolytic mixtures of each investigated ester have been assayed by a RPHPLC method using isocratic elution with methanol-water (75:25 v/v); flow rate 1 mL/min; detection at 238 nm; temperature 25 °C. Solvolytic rate constants were calculated from the obtained data. Geometry optimizations and charges calculations were carried out by Gaussian W03 software. A good correlation (R = 0.9924) was obtained between solvolytic rate constants and the polarity of the C-O2 bond of those esters. The established relation between solvolytic rate constant (K) and lipophilicity (cLogP) with experimental anti-inflammatory activity could be indicative for topical corticosteroid prodrug activation.

An application of second-order UV-derivative spectrophotometry for study of solvolysis of a novel fluocinolone acetonide ester

A novel topical corticosteroid FA-21-PhP, 2-phenoxypropionate ester of fluocinolone acetonide, has been synthesized in order to investigate the possibility of decreasing systemic side effects. In this study model system for in vitro solvolytic reaction of FA-21-PhP has been analyzed in ethanol/water (90:10, v/v) with excess of sodium hydrogen carbonate. The selected conditions have been used as in vitro model for activation of corticosteroid C-21 ester prodrug. The second-order derivative spectrophotometric method (DS) using zero-crossing technique was developed for monitoring ternary mixture of solvolysis. Fluocinolone acetonide (FA) as a solvolyte was determined in the mixture in the concentration range 0.062-0.312 mM using amplitude 2D274.96. Experimentally determined LOD value was 0.0295 mM. The accuracy of proposed DS method was confirmed with HPLC referent method. Peak area of parent ester FA-21-PhP was used for solvolysis monitoring to ensure the initial stage of changes. Linear relationship in HPLC assay for parent ester was obtained in the concentration range 0.054-0.54 mM, with experimentally determined LOD value of 0.0041 mM. Investigated solvolytic reaction in the presence of excess of NaHCO3 proceeded via a pseudo-first-order kinetic with significant correlation coefficients 0.9891 and 0.9997 for DS and HPLC, respectively. The values of solvolysis rate constant calculated according to DS and HPLC methods are in good accordance 0.038 and 0.043 h-1, respectively.

Highly enantioselective palladium-catalyzed alkylation of acyclic amides

(Chemical Equation Presented) Even acyclic amides are suitable nucleophile subtrates for asymmetric allylic alkylations. The allylation products are formed in high yields in the presence of a palladium catalyst with a 1,1′-P,N ferrocene ligand (see scheme; R = (S)-1,1′-bi-2-naphthol). The nature of the substituents on the nitrogen atom of the amide has a critical effect on the efficiency and selectivity of the reaction.

Discovery and optimization of (R)-prolinol-derived agonists of the Growth Hormone Secretagogue receptor (GHSR)

The discovery and optimization of a novel series of prolinol-derived GHSR agonists is described. This series emerged from a 11,520-member solid-phase library targeting the GPCR protein superfamily, and the rapid optimization of low micromolar hits into single-digit nanomolar leads can be attributed to the solid-phase synthesis of matrix libraries, which revealed multiple non-additive structure-activity relationships. In addition, the separation of potent diastereomers highlighted the influence of the α-methyl stereochemistry of the phenoxyacetamide sidechain on GHSR activity.

Methods for the manufacture of neofazodone

Process for the manufacture of triazolone compounds and in particular nefazodone and intermediates useful in the manufacture thereof.