7547-66-2

Usage

InChI:InChI=1/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13)/p-1/t5-/m1/s1

Upstream product

• 357-57-3 brucine 
• 51-64-9 dexamfetamine 
• 130-95-0 Quinine 
• 122674-96-8 (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate 
• 120-83-2 2,4-dichlorophenol 
• 62784-66-1 bis(1-naphthyl)methanol 
• 120-36-5 2-(2,4-dichlorophenoxy)propionic acid 
• 1356837-79-0 (R,S)-2-(2,4-dichlorophenoxy)propionyl 3-(2-pyridine)pyrazolide 
• 58048-38-7 C₁₈H₁₄Cl₄O₅ 
• 58048-37-6 2-(2,4-dichloro-phenoxy)-propionyl chloride 
• 25184-73-0 n-butyl 2-(2,4-dichlorophenoxy)propanoate 
• 3757-76-4 sodium 2,4-dichlorophenolate 
• 23844-57-7 2-(2,4-dichlorophenoxy)propanoic acid methyl ester 

Downstream Products

• 146037-75-4 (R)-2-(2,4-Dichloro-phenoxy)-propionic acid 3-chloro-1-phenyl-propyl ester 
• 119478-94-3 5'-[2(R)-(2,4-dichlorophenoxy)propionamido]-2',5'-dideoxy-5-ethyluridine 
• 865363-39-9 C₁₇H₂₄Cl₂O₃ 
• 143839-64-9 (R)-2-(2,4-dichlorophenoxy)propionyl chloride 
• 305819-40-3 methyl (2R)-[N-(2,4-dichlorophenoxy)propanoyl]glycinate 
• 97642-92-7 (R)-2-methyl-2-(2,4-dichlorophenoxy)ethanol 
• 133392-36-6 (R)-2-(2,4-Dichloro-phenoxy)-propionic acid 1-phenyl-ethyl ester 
• 146037-76-5 (R)-2-(2,4-Dichloro-phenoxy)-propionic acid 1-methyl-heptyl ester 
• 144303-42-4 (1R,6S,7S)-7-<<((R)-1-(2,4-dichlorophenoxy)ethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane 
• 144303-43-5 (1S,6R,7R)-7-<<((R)-1-(2,4-dichlorophenoxy)ethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane 
• 122674-96-8 (R)-(+)-Methyl 2-(2,4-dichlorophenoxy)propionate 

Relevant academic research and scientific papers

Access to Optically Enriched α-Aryloxycarboxylic Esters via Carbene-Catalyzed Dynamic Kinetic Resolution and Transesterification

Optically active α-aryloxycarboxylic acids and their derivatives are important functional molecules. Disclosed here is a carbene-catalyzed dynamic kinetic resolution and transesterification reaction for access to this class of molecules with up to 99% yields and 99:1 er values. Addition of a chiral carbene catalyst to the ester substrate leads to two diastereomeric azolium ester intermediates that can quickly epimerize to each other and thus allows for effective dynamic kinetic resolution to be realized. The optically enriched ester products from our reaction can be quickly transformed to chiral herbicides and other bioactive molecules.

Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor

Lactisole, an inhibitor of the human sweet taste receptor, has a 2-phenoxypropionic acid skeleton and has been shown to interact with the transmembrane domain of the T1R3 subunit (T1R3-TMD) of the receptor. Another inhibitor, 2,4-DP, which shares the same molecular skeleton as lactisole, was confirmed to be approximately 10-fold more potent in its inhibitory activity than lactisole; however the structural basis of their inhibitory mechanisms against the receptor remains to be elucidated. Crystal structures of the TMD of metabotropic glutamate receptors, which along with T1Rs are categorized as class C G-protein coupled receptors, have recently been reported and made it possible to create an accurate structural model for T1R3-TMD. In this study, the detailed structural mechanism underlying sweet taste inhibition was characterized by comparing the action of lactisole on T1R3-TMD with that of 2,4-DP. We first performed a series of experiments using cultured cells expressing the sweet taste receptor with mutations and examined the interactions with these inhibitors. Based on the results, we next performed docking simulations and then applied molecular dynamics-based energy minimization. Our analyses clearly revealed that the (S)-isomers of both lactisole and 2,4-DP, interacted with the same seven residues in T1R3-TMD and that the inhibitory potencies of those inhibitors were mainly due to stabilizing interactions mediated via their carboxyl groups in the vertical dimension of the ligand pocket of T1R3-TMD. In addition, 2,4-DP engaged in a hydrophobic interaction mediated by its o-Cl group, and this interaction may be chiefly responsible for the higher inhibitory potency of 2,4-DP.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Synthesis and structure-activity relationships of novel phenoxyacetamide inhibitors of the Pseudomonas aeruginosa type III secretion system (T3SS)

The increasing prevalence of drug-resistant bacterial infections is driving the discovery and development not only of new antibiotics, but also of inhibitors of virulence factors that are crucial for in vivo pathogenicity. One such virulence factor is the type III secretion system (T3SS), which plays a critical role in the establishment and dissemination of Pseudomonas aeruginosa infections. We have recently described the discovery and characterization of a series of inhibitors of P. aeruginosa T3SS based on a phenoxyacetamide scaffold. To better characterize the factors involved in potent T3SS inhibition, we have conducted a systematic exploration of this structure, revealing several highly responsive structure-activity relationships indicative of interaction with a specific target. Most of the structural features contributing to potency were additive, and combination of those features produced optimized inhibitors with IC50 values 1 μM.

AGROCHEMICAL COMPOSITIONS FOR INDUCING ABIOTIC STRESS TOLERANCE

The present invention relates to agrochemical formulations and uses thereof for inducing abiotic stress tolerance in plants. More specifically the invention provides agrochemical compositions comprising compounds with formula (I) which are useful to increase abiotic stress tolerance in crops.

A new method for production of chiral 2-aryloxypropanoic acids using effective kinetic resolution of racemic 2-aryloxycarboxylic acids

We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv2O) as an activating agent, bis(a-naphthyl)methanol ((α-Np)2CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.

(R,S)-2-chlorophenoxyl pyrazolides as novel substrates for improving lipase-catalyzed hydrolytic resolution

The best reaction condition of Candida antartica lipase B as biocatalyst, 3-(2-pyridyl)pyrazole as leaving azole, and water-saturated methyl t-butyl ether as reaction medium at 45°C were first selected for performing the hydrolytic resolution of (R,S)-2-(4-chlorophenoxyl) azolides (1-4). In comparison with the kinetic resolution of (R,S)-2-phenylpropionyl 3-(2-pyridyl)pyrazolide or (R,S)-α-methoxyphenylacetyl 3-(2-pyridyl)pyrazolide at the same reaction condition, excellent enantioselectivity with more than two order-of-magnitudes higher activity for each enantiomer was obtained. The resolution was then extended to other (R,S)-3-(2-pyridyl)pyrazolides (5-7) containing 2-chloro, 3-chloro, or 2,4-dichloro substituent, giving good (E > 48) to excellent (E > 100) enantioselectivity. The thermodynamic analysis for 1, 2, and 4-7 demonstrates profound effects of the acyl or leaving moiety on varying enthalpic and entropic contributions to the difference of Gibbs free energies. A thorough kinetic analysis further indicates that on the basis of 6, the excellent enantiomeric ratio for 4 and 7 is due to the higher reactivity of (S)-4 and lower reactivity of (R)-7, respectively.

INHIBITORS OF BACTERIAL TYPE III SECRETION SYSTEM

Organic compounds showing the ability to inhibit effector toxin secretion or translocation mediated by bacterial type III secretion systems are disclosed. The disclosed type III secretion system inhibitor compounds are useful for combating infections by Gram-negative bacteria such as Salmonella spp., Shigella flexneri, Pseudomonas spp., Yersinia spp., enteropathogenic and enteroinvasive Escherichia coli, and Chlamydia spp. having such type III secretion systems.

Homobenzotetramisole-catalyzed kinetic resolution of α-Aryl-, α-Aryloxy-, and α-Arylthioalkanoic acids

Effective kinetic resolutions of α-aryl-, αaryloxy-, and α-arylthioalkanoic acids have been achieved via in situ generation of their symmetrical anhydrides and enantioselective alcoholysis in the presence of homobenzotetramisole (HBTM) 3.

Separation of the phenoxy acid herbicides and their enantiomers by capillary zone electrophoresis in presence of highly sulphated cyclodextrins

The study of the chiral compounds and their fate in the environment is receiving an increasing attention - enantiomeric ratios are being measured and enantioselective degradation processes are being reported. It is particularly important with the toxic compounds like the pesticides, which are being freely used in the environment to control the harmful pests. Capillary zone electrophoresis was used for the chiral and mutual separation of four phenoxy acid herbicides using highly sulphated cyclodextrins (HSCD) in the buffer. The CE runs were performed with reverse polarity (anode in the outlet vial) using the acidic ammonium formate buffer (20 mmol, pH 3). Under these conditions of suppressed the electroendoosmotic flow (EOF), the analytes are mobilized to the anode by entering into host guest relation with the migrating negatively charged sulphated cyclodextrin. The phenoxy acid herbicides selected for the purpose were fenoprop, dicloprop, mecoprop and 2,4-DB. The α-HSCD and β-HSCD have been tested as resolving agents in the CE for the separation of the enantiomers of the herbicides. Though the chiral separation of the dicloprop and mecoprop were achieved with α-HSCD but it was not able to resolve fenoprop. With β-HSCD the required base line separation was achieved. Potential difference selected was 10 kV. The limit of detection (S/N=3) achieved in present case is 0.15 ppm for fenoprop, 0.14 ppm for dicloprop and mecoprop and 0.11 ppm for 2,4-DB.