581-96-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Naphthylacetic acid is used as a key intermediate in the synthesis of hydrolase inhibitors, which are important for the development of drugs targeting specific enzymes involved in various diseases.
Used in Peptide Chemistry:
2-Naphthylacetic acid is utilized for developing γ-dipeptide derivatives that have the ability to bind human somatostatin receptors. This application is significant in the field of medicinal chemistry, as it can lead to the discovery of novel therapeutic agents with potential use in treating a range of medical conditions.

Purification Methods

Crystallise the acid from water or *benzene. [Beilstein 9 H 666, 9 IV 2431.]

InChI:InChI=1/C12H10O2/c13-12(14)8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7H,8H2,(H,13,14)/p-1

Upstream product

• 60-29-7 diethyl ether 
• 15719-64-9 methylammonium carbonate 
• 7498-57-9 2-naphthaleneacetonitrile 
• 36660-46-5 2-(naphthalene-2-yl)-acetamide 
• 111726-64-8 3-(naphthalene-2-yl)-2-oxopropanoic acid 
• 151-50-8 potassium cyanide 
• 91-57-6 2-Methylnaphthalene 
• 93-08-3 methyl 2-naphthyl ketone 
• 2876-71-3 methyl 2-naphthylacetate 
• 201230-82-2 carbon monoxide 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 162147-96-8 2-chloro-1-(2-naphthyl)-2-(phenylsulfinyl)-1-ethanone 
• 2506-41-4 1-chloromethylnaphthalene 
• 170943-17-6 Naphthalen-2-yl-acetic acid allyl ester 

Downstream Products

• 855223-73-3 3-hydroxy-2,4-di-[2]naphthyl-3-phenyl-butyric acid 
• 67959-21-1 1t-[2]naphthyl-4t-phenyl-buta-1,3-diene 
• 109254-47-9 2-[2]naphthyl-5-phenyl-pent-2-en-4-ynoic acid 
• 37859-25-9 2-naphthylacetyl chloride 
• 1485-07-0 naphthalen-2-ethanol 
• 82326-40-7 2-(naphthalen-2-ylmethyl)-1H-benzo[d]imidazole 
• 83253-73-0 (3,3-Dimethyl-2-phenyl-aziridin-2-yl)-naphthalen-2-yl-acetic acid 
• 127035-93-2 2,6-Dimethyl-4-((E)-2-naphthalen-2-yl-vinyl)-phenol 
• 130553-61-6 N-Methyl-2-naphthalen-2-yl-N-((1R,2S)-2-pyrrolidin-1-yl-cyclohexyl)-acetamide 
• 130609-90-4 1S,2R-cis-(-)-N-methyl-N-<2-(1-pyrrolidinyl)cyclohexyl>-(2-naphthyl)acetamide 
• 130609-91-5 1R,2S-cis-(+)-N-methyl-N-<2-(1-pyrrolidinyl)cyclohexyl>-(2-naphthyl)acetamide 
• 134405-49-5 (E)-3-[2-n-Butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-naphthyl)-2-propenoic Acid 
• 110191-43-0 4-Benzyloxy-7-methyl-2-naphthalen-2-ylmethyl-1H-benzoimidazole 
• 66-99-9 β-naphthaldehyde 

Relevant academic research and scientific papers

METHOD FOR MANUFACTURING AROMATIC NITRILE COMPOUND

The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.

Visible-light photoredox-catalyzed selective carboxylation of C(sp3)?F bonds with CO2

It is highly attractive and challenging to utilize carbon dioxide (CO2), because of its inertness, as a nontoxic and sustainable C1 source in the synthesis of valuable compounds. Here, we report a novel selective carboxylation of C(sp3)?F bonds with CO2 via visible-light photoredox catalysis. A variety of mono-, di-, and trifluoroalkylarenes as well as α,α-difluorocarboxylic esters and amides undergo such reactions to give important aryl acetic acids and α-fluorocarboxylic acids, including several drugs and analogs, under mild conditions. Notably, mechanistic studies and DFT calculations demonstrate the dual role of CO2 as an electron carrier and electrophile during this transformation. The fluorinated substrates would undergo single-electron reduction by electron-rich CO2 radical anions, which are generated in situ from CO2 via sequential hydride-transfer reduction and hydrogen-atom-transfer processes. We anticipate our finding to be a starting point for more challenging CO2 utilization with inert substrates, including lignin and other biomass.

Method for preparing carboxylic acid by one-pot method

The invention discloses a method for preparing carboxylic acid by a one-pot method, which comprises the steps of carrying out a Corey-Fuchs process on 1,1-dibromo olefin under the action of n-butyllithium, reacting with isopropanol pinacol borate, quenching with hydrogen chloride, oxidizing with an oxidant, separating and purifying to obtain carboxylic acid. The method disclosed by the invention is a one-pot preparation method, is simple and convenient to operate, does not need to use metal catalysis, uses cheap and easily available reagents for reaction, is green and environment-friendly, hasmild reaction conditions and wide substrate applicability, and provides a new way for rapidly preparing a series of carboxylic acids containing different functional groups.

Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide

A simple, efficient, cheap, and broadly applicable system for the carboxylation of benzylic bromides with carbon monoxide and water is reported. Upon simple reaction with only 2.5 wt % of Pearlman's catalyst and 10 mol % of tetrabutylammonium bromide in tetrahydrofuran at 110 °C for 4 h, a range of benzylic bromides can be smoothly converted to the corresponding arylacetic acids in good to excellent yields after simple extraction and acid-base wash. The reaction was found to be broadly applicable, scalable, and could be successfully extended to the use of ex situ-generated carbon monoxide and applied to the synthesis of the nonsteroidal anti-inflammatory drug diclofenac.

BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles

Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.

Method for converting benzyl borate compounds into phenylacetic acid and derivatives thereof by carbon dioxide

The invention discloses a method for converting benzyl borate compounds into phenylacetic acid and derivatives thereof by carbon dioxide. The method comprises the steps: dissolving the benzyl borate compounds and an alkali in an organic solvent in the absence of a metal catalyst, introducing carbon dioxide into the reaction system, carrying out a reaction at the temperature of 50-150 DEG C for 3-72 hours, and acidifying to obtain phenylacetic acid or the derivatives thereof. The method is a green, simple and efficient method for synthesizing phenylacetic acid and the derivatives thereof, greenhouse gas carbon dioxide is used as a carbon source in the reaction, no transition metal catalyst is used, and the method is environmentally friendly, economical and high in efficiency.

Optimizing the Pharmacological Profile of New Bifunctional Antihyperlipidemic/Antioxidant Morpholine Derivatives

Among the causal risk factors directly promoting the development of coronary and peripheral atherosclerosis are reactive oxygen species and elevated low-density lipoprotein plasma levels. We hereby designed new potent squalene synthase (SQS) inhibitors that may simultaneously tackle the oxidative stress induced by lipid peroxidation. Using previously developed morpholine derivatives as a starting point, we conducted extensive structural changes by either substituting or modifying the morpholine ring, aiming at an optimal SQS-antioxidant pharmacological profile. Compounds 2, 3, and 7 emerged as the most potent bifunctional analogues, displaying IC50 values for SQS inhibition of 0.014, 0.16, and 0.51 μM, respectively, and further significantly decreasing lipid peroxidation of hepatic microsomal membranes. The aforementioned activities were also confirmed in vivo since the most promising derivative 2 exhibited a remarkable antihyperlipidemic and antioxidant effect. In conclusion, rational drug design accompanied by structure-activity relationship studies led to compounds combining improved antioxidant and antihyperlipidemic activity that may serve as multifunctional agents against atherosclerosis.

Design and evolution of an enzyme with a non-canonical organocatalytic mechanism

The combination of computational design and laboratory evolution is a powerful and potentially versatile strategy for the development of enzymes with new functions1–4. However, the limited functionality presented by the genetic code restricts the range of catalytic mechanisms that are accessible in designed active sites. Inspired by mechanistic strategies from small-molecule organocatalysis5, here we report the generation of a hydrolytic enzyme that uses Nδ-methylhistidine as a non-canonical catalytic nucleophile. Histidine methylation is essential for catalytic function because it prevents the formation of unreactive acyl-enzyme intermediates, which has been a long-standing challenge when using canonical nucleophiles in enzyme design6–10. Enzyme performance was optimized using directed evolution protocols adapted to an expanded genetic code, affording a biocatalyst capable of accelerating ester hydrolysis with greater than 9,000-fold increased efficiency over free Nδ-methylhistidine in solution. Crystallographic snapshots along the evolutionary trajectory highlight the catalytic devices that are responsible for this increase in efficiency. Nδ-methylhistidine can be considered to be a genetically encodable surrogate of the widely employed nucleophilic catalyst dimethylaminopyridine11, and its use will create opportunities to design and engineer enzymes for a wealth of valuable chemical transformations.

Synthetic method of fatty acid containing nitrogen heterocycle

The invention discloses a synthetic method of fatty acid containing nitrogen heterocycle. The synthetic method comprises the following steps: (S1) adding a heterocyclic compound with substitution of chloromethyl groups, a catalyst and a solvent DMF into a reaction kettle; (S2) introducing carbon dioxide to lead the pressure in the kettle to be 2-4MPa, adjusting and reacting for 10-16 hours at thetemperature of 40-50 DEG C; (S3) adding diluted hydrochloric acid into the reaction kettle to carry out acidification, using ethyl acetate for extraction, combining organic phases, carrying out rotaryevaporation to remove liquid, and further carrying out vacuum drying, thus obtaining the fatty acid containing nitrogen heterocycle. The synthetic method disclosed by the invention has the beneficialeffects that a one-pot method is adopted, the raw materials are easy to obtain, price is low, aftertreatment of products is also simpler, the universality for a substrate is also very high, and the promotion and application are easy.