7487-15-2

Usage

Uses

Used in Chemical Synthesis:
DIMETHYL 1,4-NAPHTHALENEDICARBOXYLATE is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable component in the production of pharmaceuticals, dyes, and other specialty chemicals.
Used in Coordination Chemistry:
In coordination chemistry, DIMETHYL 1,4-NAPHTHALENEDICARBOXYLATE is used as a ligand to form metal complexes. Specifically, it reacts with cyclopentadienylsodium to form (4-Methoxycarbonyl-1-naphthoyl)cyclopentadienyl M-Sn(IV) heterobimetallic complexes. These complexes have potential applications in various fields, including catalysis and materials science.
Used in Pharmaceutical Industry:
DIMETHYL 1,4-NAPHTHALENEDICARBOXYLATE is used as a building block for the development of new pharmaceutical compounds. Its unique chemical structure can be modified and functionalized to create novel molecules with potential therapeutic properties. Researchers are exploring its use in the design of new drugs targeting various diseases and medical conditions.
Used in Dye Manufacturing:
In the dye manufacturing industry, DIMETHYL 1,4-NAPHTHALENEDICARBOXYLATE is used as a key component in the synthesis of various types of dyes. Its chemical properties make it suitable for the production of dyes with specific color characteristics and stability, which are important for various applications, such as textiles, plastics, and printing inks.
Used in Materials Science:
DIMETHYL 1,4-NAPHTHALENEDICARBOXYLATE is also used in materials science for the development of new materials with specific properties. Its unique structure can be utilized to create materials with improved mechanical, thermal, or electrical properties, which can be applied in various industries, such as electronics, aerospace, and automotive.

InChI:InChI=1/C14H12O4/c1-17-13(15)11-7-8-12(14(16)18-2)10-6-4-3-5-9(10)11/h3-8H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 605-70-9 naphthalene-1,4-dicarboxylic acid 
• 67-56-1 methanol 
• 13234-52-1 1,4-naphthalenedicarboxylic acid dichloride 
• 24157-79-7 1,4-diisopropylnaphthalene 
• 83-53-4 1,4-dibromonaphthalene 
• 92191-01-0 cis-1,4-dihydro-1,4-dicarbomethoxy-naphthalene 

Downstream Products

• 143332-04-1 (+/-)-dimethyl 2-phenyl-1,2,2a,5-tetrahydroacenaphthylene-2a,5-dicarboxylate 
• 143332-04-1 (+/-)-dimethyl 2-phenyl-1,2,2a,5-tetrahydroacenaphthylene-2a,5-dicarboxylate 
• 143332-04-1 (+/-)-dimethyl 2-phenyl-1,2,2a,5-tetrahydroacenaphthylene-2a,5-dicarboxylate 
• 58791-49-4 1,4-bis(bromomethyl)naphthalene 
• 38153-01-4 naphthalene-1,4-dicarboxaldehyde 
• 131986-05-5 4-acetylnaphthalene-1-carboxylic acid 

Relevant academic research and scientific papers

Photooxygenation of an enol ether: Synthesis of exo- and endo-3,4-dioxa-2,5-dimethoxy-7,8-benzo[4.2.2.02,5] deca-7,9-diene and its chemical transformations

The reaction of singlet oxygen with 2 afforded two isomeric dioxetanes 3 and 4 which were decomposed upon heating to the expected dihydronaphthalene derivative 5. Photooxygenation of 2 in the presence of thiourea resulted in the formation of diketone 8 and ketal 7 ; the later presumably derived from incorporation of the solvent molecule.

Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids

The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.

Method for preparing 4 -acetyl -1 - naphthoic acid

The invention relates to a method for preparing 4 - acetyl -1 - naphthoic acid, and belongs to the technical field of pharmacy. The method provided by the invention is cheap and easily available 1, 4 - naphthalene dicarboxylic acid serving as a raw material, decarboxylation is carried out after erucella acid, carboxymethylating and finally hydrolyzing are carried out, 4 - acetyl -1 - naphthoic acid is obtained. The method provided by the invention can obtain the high-purity product, and the process avoids the use of the flammable metal reagent methyl zinc, is mild in reaction condition and simple to operate, and is suitable for industrial amplification production.

Design, synthesis, and biological characterization of a new class of symmetrical polyamine-based small molecule CXCR4 antagonists

CXCR4, a well-studied coreceptor of human immunodeficiency virus type 1 (HIV-1) entry, recognizes its cognate ligand SDF-1α (also named CXCL12) which plays many important roles, including regulating immune cells, controlling hematopoietic stem cells, and directing cancer cells migration. These pleiotropic roles make CXCR4 an attractive target to mitigate human disorders. Here a new class of symmetrical polyamines was designed and synthesized as potential small molecule CXCR4 antagonists. Among them, a representative compound 21 (namely HF50731) showed strong CXCR4 binding affinity (mean IC50 = 19.8 nM) in the CXCR4 competitive binding assay. Furthermore, compound 21 significantly inhibited SDF-1α-induced calcium mobilization and cell migration, and blocked HIV-1 infection via antagonizing CXCR4 coreceptor function. The structure-activity relationship analysis, site-directed mutagenesis, and molecular docking were conducted to further elucidate the binding mode of compound 21, suggesting that compound 21 could primarily occupy the minor subpocket of CXCR4 and partially bind in the major subpocket by interacting with residues W94, D97, D171, and E288. Our studies provide not only new insights for the fragment-based design of small molecule CXCR4 antagonists for clinical applications, but also a new and effective molecular probe for CXCR4-targeting biological studies.

C-C Bond-Forming and Bond-Breaking Processes from the Reaction of Diesters with Me3SnLi. Synthesis of Complex Bridged Polycycles and Dialkyl Aromatic Compounds

1,2-Aromatic diesters can be transformed into strained bridged polycyclic structures by a two-step procedure consisting of an initial reductive alkylation promoted by alkaline metals, followed by a reaction of the resulting unsaturated diesters with Me3SnLi. We propose that a stanna-Brook rearrangement plays a fundamental role in the formation of the polycyclic organotin acetals obtained. These unusual compounds could be further functionalized by tin-lithium exchange followed by alkylation of the newly formed tertiary carbanion. Alternatively, dialkylated aromatic hydrocarbons have been prepared via a decarbonilation reaction promoted by Me3SnLi. 1,4-Aromatic diesters were reductively dialkylated and then transformed into norbornadienone derivatives by reaction with Me3SnLi. Several stable dibenzonorbornadienones 41 have been prepared in just two steps starting from anthracene 38. The corresponding naphthalene analogues gave 1,4-dialkylnaphthalenes. The synthetic protocols described provide access to structures that are not easily obtained through existing synthetic methodologies.

Elucidating the Growth of Metal-Organic Nanotubes Combining Isoreticular Synthesis with Liquid-Cell Transmission Electron Microscopy

Metal-organic nanotubes (MONTs) are tunable porous 1D materials that are envisioned to be complementary to carbon nanotubes for anisotropic applications. To date, characterization of MONTs relies on single crystal X-ray diffraction (SCXRD) to determine structure and composition. This requires crystals on the micrometer regime, effectively rendering bulk 3D materials. By tracking the growth of a MONT as a function of time with liquid-cell transmission electron microscopy (LCTEM), TEM, and SCXRD, it was possible to ascertain that the material in the bulk phase matches the nanomaterial in terms of molecular structure. This result allowed for the first measurements of finite bundles of MONTs on the nanometer scale. By employing in situ LCTEM, a time course of the formation of small bundles of MONTs could be acquired which provided mechanistic information on MONT formation which is of utility in reaction optimization and applications development.

Valorization of 2,5-furandicarboxylic acid. Diels-Alder reactions with benzyne

Biomass-derived 2,5-furandicarboxylic acid was valorized by conversion to 1,4-naphthalenedicarboxylic acid via benzyne-cycloaddition and reductive aromatization in 66% overall yield (four steps). Two novel bicyclic intermediates were isolated in 80% and 98% yield. These advances diversify the potential end uses of renewable terephalic acid analogs and other furanics available from cellulose biorefinery.

NOVEL MONOMERS FROM BIOMASS

Compounds derived from biomass, e.g., cellulose and lignins, methods of forming such compounds and polymers and products formed using such compounds.

AMIDE DERIVATIVES AND THEIR USE AS INHIBITORS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1

Compounds of the formula (I) provide pharmacological agents which lower intracellular glucocorticoid concentrations in mammals, in particular, intracellular cortisol levels in humans. Therefore, the compounds of the instant invention improve insulin sensitivity in the muscle and the adipose tissue, and reduce lipolysis and free fatty acid production in the adipose tissue. The compounds of the invention lower hepatic glucocorticoid concentration in mammals, in particular, hepatic cortisol concentration in humans, resulting in inhibition of hepatic gluconeogenesis and lowering of plasma glucose levels. Thus, the compounds of the instant invention may be particularly useful in mammals as hypoglycemic agents for the treatment and prevention of conditions in which hyperglycemia and/or insulin resistance are implicated, such as type-2 diabetes. The compounds of the invention may also be used to treat other glucocorticoid associated disorders, such as Syndrome-X, dyslipidemia, hypertension and central obesity. The invention furthermore relates to the use of the compounds according to the invention for the preparation of medicaments, in particular of medicaments useful for the treatment and prevention of glucocorticoid associated disorders, by improving insulin sensitivity, reducing plasma glucose levels, reducing lipolysis and free fatty acid production, and by decreasing visceral adipose tissue formation.

EPR Studies on Carboxylic Esters. Part 15. Spin Density Distribution in the Radical Anions of Naphthalenecarboxylic Esters

Persistent radical anions of naphthalene mono-, di-, and tetracarboxylic esters are generated by in situ electroreduction.The spin density distribution is determined from the proton hfs coupling constants as measured by EPR spectroscopy and is discussed in terms of semi-empirical MO calculations.