3007-91-8

Usage

Uses

Used in Perfumery and Cosmetics Industry:
ETHYL 2-NAPHTHOATE is used as a fragrance and flavoring agent for its distinctive aromatic properties, enhancing the scent profiles in perfumes, soaps, and cosmetics. Its ability to add depth and complexity to fragrances makes it a valuable component in this industry.
Used in Organic Synthesis:
ETHYL 2-NAPHTHOATE serves as a precursor in organic synthesis, contributing to the creation of other chemical compounds. Its role in synthesis processes highlights its utility in developing new materials and substances for various applications.
Used as a Chemical Intermediate:
In the chemical industry, ETHYL 2-NAPHTHOATE is used as a chemical intermediate, playing a crucial role in the production of a range of other chemical compounds. Its intermediate status allows it to participate in multiple chemical reactions, leading to the formation of diverse end products.
Safety and Handling:
Due to its potential harmful effects if ingested or inhaled, ETHYL 2-NAPHTHOATE should be handled with care. It is recommended to store it in a cool, dry place away from direct sunlight to ensure its stability and safety. Proper safety measures, including the use of personal protective equipment, should be taken during its handling and storage to minimize health risks.

InChI:InChI=1/C13H12O2/c1-2-15-13(14)12-8-7-10-5-3-4-6-11(10)9-12/h3-9H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 2243-83-6 2-naphthaloyl chloride 
• 93-09-4 naphthalene-2-carboxylate 
• 82584-04-1 diethyl 2-(isochroman-1-yl)malonate 
• 201230-82-2 carbon monoxide 
• 91-60-1 2-Naphthalenethiol 
• 13209-15-9 1,2-bis(dibromomethyl)benzene 
• 140-88-5 ethyl acrylate 
• 13577-84-9 N,N-diethyl-2-naphthamide 
• 149358-58-7 N-benzylnaphthalene-2-carboxamide 
• 580-13-2 2-bromonaphthalene 
• 541-41-3 chloroformic acid ethyl ester 
• 7732-18-5 water 
• 4278-14-2 ethyl naphthalene-2-carboximidate hydrochloride 

Downstream Products

• 3710-23-4 2-isopropenylnaphthalene 
• 85328-29-6 α,α-diphenyl-2-naphthalene methanol 
• 613-46-7 2-naphthalenecarbonitrile 
• 1592-38-7 2-Naphthalenemethanol 
• 613-57-0 3-(naphthalen-2-yl)-3-oxopropanenitrile 
• 66-99-9 β-naphthaldehyde 
• 91-57-6 2-Methylnaphthalene 
• 118804-25-4 (2-naphthyl)diphenylmethane 
• 85328-30-9 β-naphthyldiphenylmethyl chloride 
• 39627-84-4 2-naphthohydrazide 
• 62550-65-6 ethyl 2-naphthoylacetate 
• 478282-11-0 1-(2-naphthyl)-3-phenyl-prop-2-yn-1-ol 
• 34161-87-0 ethyl 3-(4-methylphenylsulfonamido)-2-naphthoate 
• 1590-22-3 4-(2-naphthyl)-4-oxobutyric acid 

Relevant academic research and scientific papers

Solvolyses of naphthoyl chlorides. Solvent effect and Grunwald-Winstein correlation analyses with YxBnCl scales

The solvolyses of 1-naphthoyl (2), 2-naphthoyl (3), 4-methyl-1-naphthoyl (4) and 6-methoxy-2-naphthoyl (5) chlorides in a variety of solvents were studied, and correlation analyses by using the single- and dual-parameter Grunwald-Winstein equations were examined. An excellent linear relationship (R = 0.995) for 4, log (k/k0) = 0.733YxBnCl + 0.269NOTs, was observed. An SN1-like mechanism with decreasing extent of nucleophilic solvent participation was found in the solvolysis of 2 and 4.2-Naphthoyl chloride is likely to have a mechanism at the borderline of SN1-like dissociation and an addition-elimination process. 6-Methoxy-2-naphthoyl chloride shows more SN1-like character than 3 and is associated with nucleophilic solvent intervention more pronounced than that for 2 and 4. The applicability and the advantages of using the YxBnCl scale for different types of substrates are discussed. Copyright

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.

Synthesis method of beta-chloro acid ester and alpha, beta-unsaturated acid ester compound

The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of beta-chloro acid ester and an alpha, beta-unsaturated acid ester compound. The structure of the compound is characterized by 1H NMR and 13C NMR and is confirmed. The method comprises the steps of by taking acetonitrile as a solvent, carrying out fragmentation on olefin, chlorooxalic acid monoester and 2, 6-dimethyl pyridine under a photocatalytic condition to generate an alkoxyacyl free radical intermediate, carrying out free radical addition reaction on the alkoxyacyl free radical intermediate and the olefin to generate carbon free radicals, then carrying out chlorination reaction to obtain the beta-chloro acid ester compound, and carrying out dehydrochlorination reaction under a DBU condition to generate the alpha, beta-unsaturated acid ester compound. The preparation method of the compound disclosed by the invention has the advantages of starting from olefin, being mild in condition, simple and efficient, strong in functional group compatibility and wide in substrate application range, and various beta-chloro acid ester and alpha, beta-unsaturated acid ester compounds can be synthesized from highly commercialized raw materials. On the basis of photoreaction of fluid chemistry, a target product can also be obtained with a relatively good yield, and the method has very good industrial and medicinal chemistry application values.

Copper-mediated simple and direct aerobic oxidative esterification of arylacetonitriles with alcohols/phenols

A simple and direct aerobic oxidative esterification reaction of arylacetonitriles with alcohols/phenols is achieved in the presence of a copper salt and molecular oxygen, which produces a broad range of aryl carboxylic acid esters in good to high yields. Copper salt plays multiple roles in the transformation, which allows the oxygenation of C-H bond, cleavage of inert C-C bond, and formation of C-O bond in one pot without the assistance of any of the acids, bases, ligands, and so on. The reaction provides a simple, direct, and efficient protocol towards functionalized esters, especially aryl benzoates, from readily available starting materials.

4-Amino-1,2,4-triazole-3-thione-derived Schiff bases as metallo-β-lactamase inhibitors

Resistance to β-lactam antibiotics in Gram-negatives producing metallo-β-lactamases (MBLs) represents a major medical threat and there is an extremely urgent need to develop clinically useful inhibitors. We previously reported the original binding mode of 5-substituted-4-amino/H-1,2,4-triazole-3-thione compounds in the catalytic site of an MBL. Moreover, we showed that, although moderately potent, they represented a promising basis for the development of broad-spectrum MBL inhibitors. Here, we synthesized and characterized a large number of 4-amino-1,2,4-triazole-3-thione-derived Schiff bases. Compared to the previous series, the presence of an aryl moiety at position 4 afforded an average 10-fold increase in potency. Among 90 synthetic compounds, more than half inhibited at least one of the six tested MBLs (L1, VIM-4, VIM-2, NDM-1, IMP-1, CphA) with Ki values in the μM to sub-μM range. Several were broad-spectrum inhibitors, also inhibiting the most clinically relevant VIM-2 and NDM-1. Active compounds generally contained halogenated, bicyclic aryl or phenolic moieties at position 5, and one substituent among o-benzoic, 2,4-dihydroxyphenyl, p-benzyloxyphenyl or 3-(m-benzoyl)-phenyl at position 4. The crystallographic structure of VIM-2 in complex with an inhibitor showed the expected binding between the triazole-thione moiety and the dinuclear centre and also revealed a network of interactions involving Phe61, Tyr67, Trp87 and the conserved Asn233. Microbiological analysis suggested that the potentiation activity of the compounds was limited by poor outer membrane penetration or efflux. This was supported by the ability of one compound to restore the susceptibility of an NDM-1-producing E. coli clinical strain toward several β-lactams in the presence only of a sub-inhibitory concentration of colistin, a permeabilizing agent. Finally, some compounds were tested against the structurally similar di-zinc human glyoxalase II and found weaker inhibitors of the latter enzyme, thus showing a promising selectivity towards MBLs.

Construction of Esters through Sulfuryl Fluoride (SO 2 F 2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature

A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO 2 F 2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.

Intramolecular Tandem Seleno-Michael/Aldol Reaction: A Simple Route to Hydroxy Cyclo-1-ene-1-carboxylate Esters

Intramolecular tandem seleno-Michael/aldol reaction followed by an oxidation-elimination process can be an efficient tool for the construction of hydroxy cyclo-1-ene-1-carboxylate esters from oxo-α,β-unsaturated esters. Generation of lithium selenolate from elemental selenium and n-BuLi provides a simple and efficient one-pot access to cyclic endo-Morita-Baylis-Hillman adducts.

Facile, highly efficient and environmentally friendly transesterification mediated by platinum dioxide and nickel oxide under essentially neutral conditions

A practical, facile and highly efficient transesterification reaction under essentially neutral conditions was achieved using platinum dioxide (PtO2) or PtO2/nickel oxide (NiO) as the catalyst. A number of esters and alcohols that contain various functional groups were employed. Good to excellent yields were obtained for different aromatic or aliphatic starting materials. The Pt-alcohol intermediate generated in situ facilitated the exchange of low-alcohol esters to high-alcohol esters.

Ni-Catalyzed chemoselective alcoholysis of: N -acyloxazolidinones

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22-C26 segment of a close analogue of the potent immunosuppressant agent FK506.

Selective conversion of primary amides to esters promoted by KHSO4

Primary amides, either aliphatic or aromatic, are easily converted to the corresponding esters via reflux in lower primary alcohols in the presence of KHSO4. Secondary amides lead to complicated mixtures under analogous conditions, whereastertiary amides were inert. Use of isopropyl alcohol resulted inthe formation of product atslower rate and lower yieldalong withside products, whereas, use of tertiary alcoholsdid not give successful conversion andallyl and benzyl alcohol provided complex mixtures.