6279-88-5

Usage

Chemical Group

Carboxylic Acid
A group of compounds with a carboxyl functional group (-COOH).

Derived from

Naphthalene
A polycyclic aromatic hydrocarbon, serving as the base structure for the compound.

Industrial Use

Pharmaceutical Industry
Commonly used as a precursor in the synthesis of various drugs and active pharmaceutical ingredients.

Potential Properties

Anti-inflammatory, Anti-cancer
Has been studied for its possible therapeutic effects in reducing inflammation and combating cancer.

Application in Organic Synthesis

Building Block
Utilized as a fundamental component in the production of other chemicals.

Complexity

Complex Structure
Features a intricate molecular arrangement which contributes to its diverse applications.

Importance

Field of Chemistry and Pharmaceuticals
Due to its structure and applications, the compound holds a significant place in both chemistry and pharmaceuticals.

Upstream product

• 7664-93-9 sulfuric acid 
• 5337-63-3 ethyl 2-(2-phenylethyl)acetoacetate 
• 124-38-9 carbon dioxide 
• 4373-13-1 4-methyl-1,2-dihydronaphthalene 

Downstream Products

• 20027-77-4 5,6-dimethyl-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

EtAlCl2/2,6-Disubstituted Pyridine-Mediated Carboxylation of Alkenes with Carbon Dioxide

α-Arylalkenes and trialkyl-substituted alkenes undergo carboxylation with CO2 in the presence of EtAlCl2 and 2,6-dibromopyridine to afford the corresponding α,β- and/or β,γ-unsaturated carboxylic acids. This reaction is suggested to proceed via the electrophilic substitution of EtAlCl2 with the aid of the base, followed by the carbonation of the resulting ate complex. This reaction can be applied to terminal dialkylalkenes by using a mixture of 2,6-di-tert-butylpyridine and 2,6-dibromopyridine.

Cyclization of arylacetoacetates to indene and dihydronaphthalene derivatives in strong acids. Evidence for involvement of further protonation of O,O-diprotonated β-ketoester, leading to enhancement of cyclization

The chemical features, such as substrate stability, product distribution, and substrate generality, and the reaction mechanism of Bronsted superacid-catalyzed cyclization reactions of aromatic ring-containing acetoacetates (β-ketoesters) were examined in detail. While two types of carbonyl cyclization are possible, i.e., keto cyclization and ester cyclization, the former was found to take place exclusively. The reaction constitutes an efficient method to synthesize indene and 3,4-dihydronapthalene derivatives. Acid-base titration monitored with 13C NMR spectroscopy showed that the acetoacetates are fully O1,O3-diprotonated at H 0) -11. While the five-membered ring cyclization of the arylacetoacetates proceeded slowly at H0) -11, a linear increase in the rate of the cyclization was found with increasing acidity in the high acidity region of H0) -11.8 to -13.3. Therefore, the O 1,O3-diprotonated acetoacetates exhibited some cyclizing reactivity, but they are not the reactive intermediates responsible for the acceleration of the cyclization in the high acidity region. The reactive cationic species might be formed by further protonation (or protosolvation) of the O1,O3-diprotonated acetoacetates; i.e., they may be tricationic species. Thermochemical data on the acid-catalyzed cyclization of the arylacetoacetates showed that the activation energy is decreased significantly as compared with that of the related acid-catalyzed cyclization reaction of a compound bearing a single functional group, such as a ketone. These findings indicate that intervention of the trication contributes to the activation of the cyclization of arylacetoacetates in strong acid, and the electron-withdrawing nature of the O-protonated ester functionality significantly increases the electrophilicity of the ketone moiety.

3,4-dihydro-2-naphthamide derivatives as selective dopamine D3 ligands

The invention relates to 3,4-dihydro-2-naphthamide derivatives of formula (I), pharmaceutical compositions containing them and their therapeutic applications as partial agonists or antagonists of the dopamine D3 receptor for the treatment of neuropsychological disorders.