20576-83-4

Upstream product

• 6725-72-0 4-methoxycarbonylbenzoic acid phenyl ester 
• 19851-61-7 p-dibenzyl benzenedicarboxylate 
• 25061-09-0 4-chlorocarbonylbenzoic acid phenyl ester 
• 108-95-2 phenol 
• 100-20-9 terephthaloyl chloride 
• 67852-95-3 4-benzyloxycarbonyl-benzoyl chloride 
• 18520-63-3 monobenzyl terephthalate 

Downstream Products

• 123688-95-9 phenyl 4-(4-octyloxyphenoxycarbonyl)benzoate 
• 6051-43-0 terephthalamic acid 
• 1257841-69-2 1-phenyl 4-pyridin-2-yl benzene-1,4-dicarboate 
• 17847-33-5 phenyl 4-cyanobenzoate 
• 25061-09-0 4-chlorocarbonylbenzoic acid phenyl ester 

Relevant academic research and scientific papers

Cleavage of Carboxylic Esters by Aluminum and Iodine

A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.

Selective deprotection and amidation of 2-pyridyl esters via N-methylation

The 2-pyridyl residue serves as a protecting group for various carboxylic acids. The protecting group is selectively cleaved under mild conditions via N-methylation of the pyridyl group. During the deprotection process, the various functional groups as we

Synthesis and structure - Activity relationships of N -(2-Oxo-3-oxetanyl) amides as N -acylethanolamine-hydrolyzing acid amidase inhibitors

The fatty acid ethanolamides (FAEs) are a family of bioactive lipid mediators that include the endogenous agonist of peroxisome proliferator- activated receptor-α, palmitoylethanolamide (PEA). FAEs are hydrolyzed intracellularly by either fatty acid amide hydrolase or N-acylethanolamine- hydrolyzing acid amidase (NAAA). Selective inhibition of NAAA by (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide [(S)-OOPP, 7a] prevents PEA degradation in mouse leukocytes and attenuates responses to proinflammatory stimuli. Starting from the structure of 7a, a series of β-lactones was prepared and tested on recombinant rat NAAA to explore structure-activity relationships (SARs) for this class of inhibitors and improve their in vitro potency. Following the hypothesis that these compounds inhibit NAAA by acylation of the catalytic cysteine, we identified several requirements for recognition at the active site and obtained new potent inhibitors. In particular, (S)-N-(2-oxo-3-oxetanyl)biphenyl-4-carboxamide (7h) was more potent than 7a at inhibiting recombinant rat NAAA activity (7a, IC50 = 420 nM; 7h, IC50 = 115 nM) in vitro and at reducing carrageenan-induced leukocyte infiltration in vivo.

Mechanism of the catalytic oxidation of tertiary alcohols by the water- soluble Mn-TMPyP/KHSO5 system: β-Fragmentation versus O-neophyl rearrangement

Oxidation of 4-(1-hydroxy-1-phenylethyl)benzoic acid HPEBA with a water- soluble metalloporphyrin as catalyst and KHSO5 as oxygen atom donor gives the major products, acetophenone AC and acetylbenzoic acid ABA, by a C(aliph)-C(Ar) bond cleavage, but a minor product, benzoyloxybenzoic acid BOBA, requires the insertion of an oxygen atom to form the ester. This compound becomes the main oxidation product on increasing the amount of acetonitrile in the reaction medium, and its formation is oxygen-dependent. The conversion is drastically lowered by using D2O instead of H2O, suggesting that an alkoxyl radical is formed in the rate-determining step. Labeling experiments using 18O2 or H218O under different reaction conditions show that the carbonyl oxygen atoms of AC and ABA originate either from substrate, water or dioxygen. However, the carbonyl oxygen atom in the ester group of BOBA originates from dioxygen while the other oxygen atom of the ester remains unlabeled. These results can be explained by an O-neophyl rearrangement of the initial alkoxyl radical to afford a carbon-based radical which then reacts with dioxygen or Mn(IV)-OH/water. In a competitive reaction pathway, direct β-scission of the alkoxyl radical leads to unlabeled products. The oxidation of other tertiary diaryl alcohols is also discussed.

Molecular structure and smectic properties. Part 1. The effect of linkages on smectic A thermal stability in three aromatic ring compounds linked by ester groups

The thermal properties of phenyl 4-(4-alkoxybenzoyloxy)benzoates (1), 4-alkoxyphenyl 4-benzoyloxybenzoates (2), 4-(4-alkoxybenzoyloxy) benzoyloxyxylenes (3), and phenyl 4-(4-alkoxyphenoxycarbonyl)benzoates (4) have been examined. In spite of the structural similarity, the smectic nature of the series is quite different. Series (1) shows a stable smectic A phase starting with the hexyloxy homologue. Series (2) and (3) do not show any smectic phases, and the potential smectic stabilities evaluated from the binary phase diagrams are quite low. Although series (4) shows no smectic phase because of higher melting points, this series intrinsically possesses a smectic A nature, where the potential smectic A - nematic transition temperatures are as high as those of series (1). The difference in the smectic nature for these four series is discussed in terms of the geometrical and electrocstatic properties of the molecules, and a new basis for the thermal stability of the smectic A phase has been proposes.

New Reagents: Part 5 - Aluminium Chloride-Sodium Iodide System as a Highly Selective Reagent for Non-hydrolytic Cleavage of Esters

Aluminium chloride-sodium iodide is found to be a highly selective reagent for non-hydrolytic cleavage of esters.This reagent is almost ineffective towards phenyl esters and aryl alkyl ethers.