15023-58-2

Upstream product

• 106-43-4 para-chlorotoluene 
• 106-48-9 4-chloro-phenol 
• 15023-67-3 4-nitrophenyl 4-methylbenzoate 
• 24573-38-4 4-chlorophenolate 
• 99-94-5 p-Toluic acid 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 116544-78-6 (5-chloro-2-hydroxyphenyl)(p-tolyl)methanone 
• 94797-02-1 4-Methyl-benzoic acid 2-benzoyl-4-chloro-phenyl ester 
• 52980-99-1 5-chloro-2-methoxy-4'-methylbenzophenone 
• 85-19-8 (5-chloro-2-hydroxyphenyl)phenylmethanone 
• 55082-69-4 2-(4-methylphenyl)-3-phenyl-5-chlorobenzofuran 
• 99-94-5 p-Toluic acid 
• 116544-64-0 (2-Benzoyl-4-chloro-phenoxy)-p-tolyl-acetic acid 
• 116544-54-8 (2-Benzoyl-4-chloro-phenoxy)-p-tolyl-acetic acid ethyl ester 
• 1203576-57-1 C₁₄H₁₀BrClO₂ 

Relevant academic research and scientific papers

The effect of acyl substituents on the α-effect: Contrasting α-effect profiles for reactions of 4-nitrophenyl substituted benzoates with neutral and anionic nucleophiles

The magnitude of the α-effect for reactions of 4-nitrophenyl substituted benzoates with a pair of anionic nucleophiles is independent of the electronic nature of the acyl substituent, while the one for the corresponding reactions with a pair of neutral nucleophiles increases as the acyl substituent changes from a strong electron withdrawing substituent to electron donating ones.

Activation parameters of the reactions of 4-nitrophenyl benzoates and S-phenyl benzothioate with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate

The kinetics of transesterification of 4-nitrophenyl benzoates and S-phenyl benzothioate with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate were studied. Variation of the substrate reactivity and activation parameters of the process is discussed with respect to the substituent in the benzoic acid fragment.

Design, synthesis, and biological evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase

Based on the results of computational docking to the active site of the cytochrome P450 14α-demethylase (CYP51), a series of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols as analogs of fluconazole were designed, synthesized, and evaluated as antifungal agents. The MIC80 values indicate that compounds 1a-n exhibited higher activity against nearly all fungi tested except Aspergillus fumigatus than fluconazole, while compounds 2a-f, 3a-f showed no activity or only moderate activity against all fungi tested. Noticeably, the MIC value of compounds 1a, 1b and 1g is 64 times lower than that of fluconazole against Microsporum gypseum in vitro. And compounds 1a, 1b and 2b showed 128 times higher activity (with the MIC80 value of 0.0039 μg/mL) than that of fluconazole against Candida albicans and also showed higher activity than that of the other positive controls. Computational docking experiments indicated that the inhibition of CYP51 involves a coordination bond with iron of the heme group, the hydrophilic H-bonding region, the hydrophobic region, and the narrow hydrophobic cleft. In addition, the activity of the compounds would be enhanced when the side chains were shorter.

Kinetics of the reaction of 4-nitrophenyl benzoates with 4-chlorophenol in the presence of potassium carbonate in dimethylformamide

The effect of the substituent in the benzoyl group on the relative rate and activation parameters of transesterification of substituted 4-nitrophenyl benzoates with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate was studied by the competing reaction technique. The whole series of benzoates showed the enthalpy-entropy compensation effect. 4-Nitrophenyl benzoates having electronacceptor substituents give rise to isokinetic relationship with an isokinetic temperature β of 382 K. The mechanism of the transesterification process is discussed. Pleiades Publishing, Inc., 2006.

Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents

Carbonyl carbon 13C NMR chemical shifts δC(C=O) measured in this work for a wide set of substituted phenyl benzoates p-Y-C 6H4CO2C6H4-p-X (X = NO2, CN, Cl, Br, H, Me, or MeO; Y = NO2, Cl, H, Me, MeO, or NMe2) have been used as a tool to study substituent effects on the carbonyl unit. The goal of the work was to study the cross-interaction between X and Y in that respect. Both the phenyl substituents X and the benzoyl substituents Y have a reverse effect on δC(C=O). Electron-withdrawing substituents cause shielding while electron-donating ones have an opposite influence, with both inductive and resonance effects being significant. The presence of cross-interaction between X and Y could be clearly verified. Electronic effects of the remote aromatic ring substituents systematically modify the sensitivity of the C=O group to the electronic effects of the phenyl or benzoyl ring substituents. Electron-withdrawing substituents in one ring decrease the sensitivity of δC(C=O) to the substitution of another ring, while electron-donating substituents inversely affect the sensitivity. It is suggested that the results can be explained by substituent-sensitive balance of the contributions of different resonance structures (electron delocalization, Scheme 1).

Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p-chlorophenoxide

The Hammett plots obtained for the title-reactions exhibit a break, i.e. ρ acyl values decrease from 2.21 ~ 2.44 to 1.45 ~ 1.52 as the acyl substituent becomes a strong electron withdrawing group (σ > 0.6). Such a break in the Hammett plots is suggestive of a change in the reaction mechanism and strong evidence of a stepwise mechanism for the acyl-transfer reaction.