17362-17-3

Usage

Uses

Used in Pharmaceutical Research:
3-(4-Hydroxyphenyl)propionitrile is used as a research tool for evaluating the biological role of estrogen receptor beta (ERβ). It aids in understanding the mechanisms of action and potential therapeutic applications of ERβ-targeting drugs, which can be crucial in developing treatments for various diseases and conditions.
Used in Chemical Synthesis:
In the field of organic chemistry, 3-(4-Hydroxyphenyl)propionitrile can be employed as a starting material or intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for further functionalization and modification to create novel compounds with desired properties.
Used in Analytical Chemistry:
3-(4-Hydroxyphenyl)propionitrile can also be utilized in analytical chemistry for the development of new methods and techniques for the detection and quantification of related compounds. Its distinct chemical properties make it a valuable reference standard in chromatographic, spectroscopic, and other analytical assays.

InChI:InChI=1/C9H9NO/c10-7-1-2-8-3-5-9(11)6-4-8/h3-6,11H,1-2H2

Upstream product

• 10139-91-0 3-(4-aminophenyl)-propionitrile 
• 107-13-1 acrylonitrile 
• 108-95-2 phenol 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 7664-93-9 sulfuric acid 
• 22442-48-4 3-(4-methoxyphenyl)propionitrile 
• 53563-09-0 3-(4-nitrophenyl)propanenitrile 
• 23838-70-2 3-(4-hydroxyphenyl)propanoic acid amide 
• 76793-81-2 (Rh(NH₃)5(4-HO-hcn))(ClO₄)3 
• 156-38-7 4-hydroxyphenylacetate 
• 7677-24-9 trimethylsilyl cyanide 
• 82575-52-8 3-(4-hydroxyphenyl)prop-2-ene nitrile 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 60-82-2 3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on 
• 111316-17-7 4,2′,4′-trihydroxy-6′-methoxydihydrochalcone 
• 520-42-3 asebogenin 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 99855-93-3 [4-(2-carbamoyl-ethyl)-phenoxy]-acetic acid 
• 29112-50-3 3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionitrile 
• 133883-37-1 4-(5-Hexyl-pyrimidin-2-yl)-benzoic acid 4-(2-cyano-ethyl)-phenyl ester 
• 107223-45-0 3-[4-(4-Acetyl-2-ethyl-3-hydroxy-benzyloxy)-phenyl]-propionitrile 
• 97581-59-4 3-[4-(4-Acetyl-3-hydroxy-2-propyl-benzyloxy)-phenyl]-propionitrile 
• 81978-12-3 7-Butyl-9,10-dihydro-phenanthrene-2-carboxylic acid 4-(2-cyano-ethyl)-phenyl ester 
• 81978-18-9 7-Pentyl-9,10-dihydro-phenanthrene-2-carboxylic acid 4-(2-cyano-ethyl)-phenyl ester 
• 57400-89-2 4-(3-aminopropyl)phenol 
• 310869-83-1 3-(4-tetradecyloxyphenyl)propionitrile 
• 166959-67-7 4-(2-cyanoethyl)phenyl(trifluoromethyl)sulfonate 

Relevant academic research and scientific papers

A Titanium-Catalyzed Reductive α-Desulfonylation

A titanium(III)-catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α-sulfonyl nitriles, circumventing traditional base-mediated α-alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α-desulfonylation of ketones. In addition, a one-pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst-dependent mechanism involving a homolytic C?S cleavage.

Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists

A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.

Formal reductive addition of acetonitrile to aldehydes and ketones

An efficient and highly productive rhodium-catalyzed method for the synthesis of nitriles employing aldehydes or ketones, methyl cyanoacetate, water and carbon monoxide as starting materials has been developed. Simple rhodium chloride without any ligands can be used. The fine tuning of the substrate can lead to the activity higher than 5000 TON.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Indium(III)-catalyzed one-pot synthesis of alkyl cyanides from carboxylic Acids

The one-pot preparation of alkyl cyanides from carboxylic acids via alkyl iodides or alkyl bromides, which were in situ generated either by indium(III)-catalyzed reductive iodination or bromination of carboxylic acids, is described. Georg Thieme Verlag Stuttgart New York.

Terphenyl-based helical mimetics that disrupt the p53/HDM2 interaction

(Chemical Equation Presented) HDM2 regulates p53 by binding to its transactivation domain and promoting its ubiquitin-dependent degradation. Crystallographic analysis of the HDM2/p53 complex revealed that three hydrophobic residues (F19, W23, L26) along one face of the p53 helical peptide are essential for binding (see picture). Terphenyl-based antagonists mimic the α-helical region of p53 and disrupt HDM2/p53 complexation.

Inhibition of secretory phospholipase A2. 2-Synthesis and structure-activity relationship studies of 4,5-dihydro-3-(4-tetradecyloxybenzyl) -1,2,4-4H-oxadiazol-5-one (PMS1062) derivatives specific for group II enzyme

We have recently reported the discovery of a series of specific inhibitors of human group IIA phospholipase A2 (hGIIA PLA2) to display promising in vitro and in vivo properties. Here we describe the influence of different structural modifications on the specificity and potency against hGIIA PLA2 versus porcine group IB PLA2. The SAR results, as well as the log P and pKa values of oxadiazolone determined in this work, provide important information towards the comprehension of the mode of action of this kind of compounds.

Transformation of oximes of phenetyl ketone derivatives to quinolines and azaspirotrienones catalyzed by tetrabutylammonium perrhenate and trifluoromethanesulfonic acid

Phenethyl ketone oximes are converted to quinolines by the treatment with tetrabutylammonium perrhenate, trifluoromethanesulfonic acid, and chloranil in refluxing 1,2-dichloroethane. Azaspirotrienones can be synthesized from p-hydroxyphenethyl or 3-(p-hydroxyphenyl)propyl ketone oximes by applying the above method. Thus prepared azaspirotrienones are converted to quinolines by acid treatment.

Synthesis of Azaspirodienones via Intramolecular Cyclization of p-Hydroxybenzylacetone Oximes and Their Transformation into Quinolines

Intramolecular cyclization reaction on the nitrogen atom of oximes of p-hydroxybenzylacetone derivatives proceeds by the treatment with tetrabutylammonium perrhenate and trifluoromethanesulfonic acid in refluxing 1,2-dichloroethane to afford azaspirodienones in good yield.The azaspirodienones are transformed into quinolines via dienone-phenol rearrangement.

Intramolecular energy transfer in a rhodium(III) metalloorganic bichromophore system. Photochemical and photoluminescence studies

Reported are the photochemical, photoluminescence, and spectral studies of a series of pentaammine(organonitrilo)rhodium(III) compounds, Rh(NH3)5(N≡C-R)3+ (where R is a phenyl, benzyl, or 2-phenylethyl group or a substituted derivative). The absorption spectroscopy exhibits features attributable to both ππ* and ligand field transitions. The luminescence spectra, however, exhibit only ligand field (LF) emissions regardless of whether the ππ* or LF states are initially populated. The luminescence lifetimes at 77 K are also characteristic of LF states. Irradiation of the ππ* or LF bands in aqueous solutions leads to photosubstitution of the organonitrile ligand with the quantum yields being somewhat smaller for λirr = 254 nm (ππ*) than 313 nm (LF) in most cases. The results are discussed in terms of the efficiency of interconfigurational energy transfer between ππ* and LF states.