13633-87-9

Usage

InChI:InChI=1/C9H7ClO2/c1-2-9(11)12-8-5-3-7(10)4-6-8/h2-6H,1H2

Upstream product

• 814-68-6 acryloyl chloride 
• 1193-00-6 sodium 4-chlorophenolate 
• 106-48-9 4-chloro-phenol 
• 86259-99-6 4'-chlorophenyl 3-bromopropionate 
• 79-10-7 acrylic acid 

Downstream Products

• 144261-54-1 3-phenyl-3-hydroxy-2-methylene-propanoic acid p-chlorophenyl ester 
• 1210408-68-6 1-(4-chlorophenyl) 2,3,4,5-tetramethyl benzene-1,2,3,4,5-pentacarboxylate 
• 1210408-78-8 1-(4-chlorophenyl) 2,3,4,5-tetraethyl benzene-1,2,3,4,5-pentacarboxylate 
• 1586777-29-8 C₂₁H₁₅ClN₂O₃ 
• 1620141-46-9 (R)-4-chlorophenyl 4-nitro-4-(phenylsulfonyl)pentanoate 
• 79-10-7 acrylic acid 
• 117928-47-9 1,4,5,6-Tetrabromo-7,7-dimethoxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 4-chloro-phenyl ester 

Relevant academic research and scientific papers

Acid- And base-switched palladium-catalyzed γ-C(sp3)-H alkylation and alkenylation of neopentylamine

The functionalization of remote unactivated C(sp3)-H and the reaction selectivity are among the core pursuits for transition-metal catalytic system development. Herein, we report Pd-catalyzed γ-C(sp3)-H-selective alkylation and alkenylation with removable 7-azaindole as a directing group. Acid and base were found to be the decisive regulators for the selective alkylation and alkenylation, respectively, on the same single substrate under otherwise the same reaction conditions. Various acrylates were compatible for the formation of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. The alkenylation protocol could be further extended to acrylates with natural product units and α,β-unsaturated ketones. The preliminary synthetic manipulation of the alkylation and alkenylation products demonstrates the potential of this strategy for structurally diverse aliphatic chain extension and functionalization. Mechanistic experimental studies showed that the acidic and basic catalytic transformations shared the same six-membered dimer palladacycle.

Kinetic studies of conjugate addition of amines to allenic and acrylic esters and their correlation with antibacterial activities against Staphylococcus aureus

Abstract: Kinetic reactivities of various allenic and acrylic esters in conjugate addition reactions with various amines were investigated. Competition experiments showed that amines reacted selectively with allenic esters, which was also confirmed by quantitative determination of the rate constants. The antibacterial activity against Staphylococcus aureus of allenic and acrylic ester derivatives were also determined. Allenic esters were found to exhibit a higher antibacterial activity than its acrylic counterparts. A correlation between the kinetic property and the antibacterial activity suggested that a conjugate addition may involve in the antibacterial mechanism of these unsaturated esters. Graphical abstract: [Figure not available: see fulltext.].

How much does the hybridization of a carbon atom affect the transmission of the substituent effect on the chemical shift?

1H and 13C NMR spectra of aryl esters of propionic acid, acrylic acid, and propiolic acid were systematically examined to find out the substituent effect on the chemical shift. The values of the chemical shift of the carbonyl carbon showed an inverse correlation with the Hammett ?3 values, and the magnitude of the slope was the largest with the propiolates. The ?± carbons of acrylates and propiolates also showed an inverse correlation with much smaller values of the slopes than those of the carbonyl carbons; but those of the propionates showed absolutely no correlation. However, the ?2 carbons of acrylates and propiolates showed normal correlation with larger values of the slopes. The signs and the magnitudes of the slopes may be understood by the transmission of the substituent electronic effect through bonds as well as through space. The propiolyloxy group also showed a significantly large effect on the 13C chemical shift values of the benzene ring.

Enantio- and diastereoselective organocatalytic α-alkylation of aldehydes with 3-substituted 2-(bromomethyl)acrylates

The catalytic direct α-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to α-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.

The 'Baylis - Hillman reaction' mechanism and applications revisited

It is shown that reaction of aryl, benzyl, alkyl and functionalised alkyl acrylic esters with benzaldehyde, in the presence of 1,4-diazabicyclo[2.2.2] octane, strongly depends upon the electronic and steric effects of the ester part. This influence is also observed in condensation of furfuraldehyde. Moreover, for the first time, it is shown that the overall condensation is equilibrated.

FURTHER STUDY OF ESTERTIN TRICHLORIDES, Cl3SnCH2CH2CO2R. LEWIS ACIDITY TOWARDS ACETONITRILE. CRYSTAL STRUCTURE OF Cl3SnCH2CH2CO2Pr-i

Crystals of Cl3SnCH2CH2CO2Pr-i are orthorombic, space group P212121 with a 9.638(6), b 10.004(7) and c 12.848(8) Angstroem.The tin atom is five-coordinate with two chlorines and carbon equatorial and the remaining chlorine and the carbonyl oxygen axial, in a distorted trigonal-bipyramidal arrangement: (Sn-Cl)ax 2.389(3), average (Sn-Cl)eq 2.320(2), Sn-C 2.142(9), Sn-O 2.337(5) Angstroem.Apart from the equatorial chlorine and the terminal carbons in the isopropyl group, all non-hydrogen atoms are essentially coplanar.The molecule approaches C2v symmetry although not constrained to do so by the crystallographic space group.In MeCN solution, the compounds Cl3SnCH2CH2CO2R (I, R = Me, Pr-i, C6H4X (X = p-MeO, H, p-Cl, o-MeO) or C6H3Cl2-2,4) form as equilibrium mixtures of 1/1 and 2/1 MeCN/1 complexes; the chelate ring is broken in the 2/1 complexes.Equilibrium constants indicate that the strength of the intramolecular Sn-O coordination I increases with the electron releasing ability of the R group.

Dehydrobromination of Some Substituted Phenyl 3-Bromopropionates and Phenyl 3-Bromothiolopropionates. Transmission of Activation Effects through Acyl Bonds

Thirteen aryl 3-bromopropionates and nine aryl 3-bromothiolopropionates were prepared and subjected to dehydrohalogenation with sodium 3,4-dinitrophenoxide in dry tetrahydrofuran at 34.25 deg C.The second-order rate constants for the sulfur esters were approximately 10 times those for the corresponding oxygen esters.Good Hammett plots with ρ's of +0.81+/-0.04 and 0.98+/-0.04 for the oxygen and sulfur series, respectively, were obtained by using ?n.Activation parameters were measured for two oxygen and two sulfur esters; in both bases, low (12-13 kcal/mol) activatio n enthalpies and moderately large negative (19-21 eu) activation entropies were found.At 34.25 deg C, 3'-nitrophenyl 3-bromopropionate dehydrohalogenated 14 times more rapidly than 3'-nitrophenyl 3-chloropropionate; phenyl 3-bromothiolopropionate dehydrohalogenated 11 times more rapidly than the phenyl 3-chlorothiolopropionate.The rate constant ratio for 4'-bromophenyl 3-bromopropionate vs. 4'-bromophenyl 3-bromopropionate-2-d was 1.84; the monodeuterated compound yielded olefinic product with 65percent D.H was abstracted preferentially from 4'-chlorophenyl 3-bromothiolopropionate partially deuterated in the 2-position, but no kinetic results were obtained.No evidence of reversibility was found with 2,4-dinitrophenol-d, and the addition of 2,4-dinitrophenol to kinetic mixtures had essentially no effect on the rate conatants.The results are interpreted to indicate an E2 process near the EL/E1cB borderline with the thiolo ester deviating somewhat more toward an E1cB-I process.

Control of the 'Extended' E1cB Mechanism of Acyl Group Transfer in Activated Esters of Acrylic Acids

Aminolysis and alkaline hydrolysis of aryl propenoates are shown to proceed via a normal nucleophilic substitution mechanism.The 'extended' E1cB mechanism of hydrolysis involving attack of hydroxide ion at the β-carbon followed by expulsion of the phenolate ion from the resulting carbanion is shown not to occur with the parent propenoate.The 'extended' E1cB mechanism is taken by the hydrolysis of 2-cyano-3-(4-methoxyphenyl)propenoate esters due to the stabilising effect of the cyano-group on the intermediate carbanion.