213455-52-8

Usage

Structure

Substituted naphthalene derivative with a carboxaldehyde group and a phenylmethoxy substituent

Usage

Fragrance ingredient in cosmetic and personal care products, manufacturing of perfumes and fragrances, synthesis of other organic compounds, development of pharmaceuticals and agrochemicals

Biological and pharmacological activities

Potential anti-inflammatory and analgesic properties

Precautions

Potential health and environmental hazards, should be handled and used with caution.

Upstream product

• 7770-45-8 4-hydroxy-1-naphthaldehyde 
• 100-44-7 benzyl chloride 
• 23084-88-0 diphenylmethyl vinyl ether 
• 666829-65-8 benzyl 2-ethynylbenzoate 
• 100-39-0 benzyl bromide 
• 666829-83-0 benzyl 2-[2-(trimethylsilyl)ethynyl]benzoate 
• 607-58-9 1-(phenylmethoxy)naphthalene 
• 68-12-2 N,N-dimethyl-formamide 
• 100-51-6 benzyl alcohol 
• 205250-12-0 2-[(trimethylsilanyl)ethynyl]benzoic acid 
• 111-34-2 -butyl vinyl ether 

Downstream Products

• 401468-83-5 2-Phenoxy-3-(4-benzyloxynaphthalen-1-yl)-2-methylpropionic acid ethyl ester 
• 728033-53-2 5-hydroxy-1-benzyloxy-4-naphthalenecarboxaldehyde 
• 87344-63-6 4-benzyloxy-1-naphthoic acid 

Relevant academic research and scientific papers

Palladium-Catalyzed Regiospecific peri- And ortho-C-H Oxygenations of Polyaromatic Rings Mediated by Tunable Directing Groups

An efficient divergent approach of Pd-catalyzed C-H oxygenation of polyaromatic rings is described. Reversible directing groups enable regiospecific peri- and ortho-oxygenation to readily access a wide array of polyaromatic phenols without pre- and postmanipulation of directing groups. The systematic mechanistic investigation, including deuterium-labeling experiments, palladacycle trapping, and DFT calculations, reveals that the tunable ligand-assisted C-H bond cleavage played a crucial role during the reaction process.

Synthesis of Phenalenyl-Fused Pyrylium Cations: Divergent C?H Activation/Annulation Reaction Sequence of Naphthalene Aldehydes with Alkynes

Described herein is the synthesis of stable oxonium-doped polycyclic aromatic hydrocarbons (PAHs) by the rhodium-catalyzed C?H activation/annulations of naphthalene-type aldehydes with internal alkynes. This protocol provides four divergent reaction types, including two unexpected annulations with an oxygen transposition process, which lead to diverse types of phenalenyl-fused pyrylium cations comprising a four-, five-, or six-ring-fused π-conjugated core. The annulations exhibit an exquisite regioselectivity and a high tolerance of sensitive functional groups. These PAHs feature intriguing photophysical properties such as full-color tunable fluorescence emission, high quantum yield, and positively charged core, and can be reduced easily to the phenalenyl radicals.

Arylthiosemicarbazones as antileishmanial agents

Based on a screening process, we targeted substituted thiosemicarbazone as potential antileishmanial agents. Our objective was to identify the key structural elements contributing to the anti-parasite activity that might be used for development of effective drugs. A series of 32 compounds was synthesized and their efficacy was evaluated against the clinically relevant intracellular amastigotes of Leishmania donovani. From these, 22 compounds showed EC50values below 10?μM with the most active derivative (compound 14) showing an EC50of 0.8?μM with very low toxicity on two different mammalian cell lines. The most relevant structural elements required for higher activity indicate that the presence of a fused bicyclic aromatic ring such as a naphthalene bearing an alkyl or an alkoxy group substituent are prerequisites. Owing to the easy synthesis, high activity and low toxicity, the most active compounds could be considered as a lead for further development.

NOVEL CERCOSPORAMIDE DERIVATIVE

The present invention relates to a novel cercosporamide derivative, a pharmacologically acceptable salt thereof or an ester thereof which has an excellent hypoglycemic effect and is useful as a therapeutic and/or prophylactic agent for diabetes. A cercosporamide derivative having the general formula (I): [wherein X represents an oxygen atom or the like, R1 represents a hydrogen atom or a C1-C6 alkyl group, R2 represents a hydrogen atom, a C1-C6 alkyl group or a C1-C6 halogenated alkyl group, R3 represents a hydrogen atom or a C1-C6 alkyl group, R4 represents a C6-C10 aryl group which may be substituted with one to five group(s) independently selected from Substituent Group a, or the like, n represents 1, 2 or 3, and Substituent Group a represents a halogen atom, a C1-C6 alkyl group, a C1-C6 halogenated alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 alkoxy group, a C1-C6 halogenated alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group and the like], a pharmacologically acceptable salt thereof or an ester thereof.

Synthesis of naphthalene derivatives through platinum(II)-catalyzed reaction of 2-alkynylbenzoates with vinyl ethers

A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes has been developed by the PtCl 2-catalyzed reaction of o-ethynylbenzoates or benzothioates with vinyl ethers. Treatment of o-alkynylbenzoate derivatives with PtCl2 generated the platinum(II)-containing carbonyl ylides as a key reactive intermediate and these species reacted with vinyl ethers to give substituted naphthalenes in good yields. The presence of the platinum-containing carbonyl ylide was confirmed by NMR analyses of the mixture of o-ethynylbenzoate and [PtCl2(H2C=CH2)]2. Furthermore, it was suggested that the naphthalene derivatives were produced by [3+2] cycloaddition of the ylide species with vinyl ethers, followed by 1,2-alkyl migration of the generated platinum-carbene intermediates. Georg Thieme Verlag Stuttgart.

Platinum(II)-Catalyzed Reaction of 2-Alkynylbenzoates or Benzothioates with Vinyl Ethers: A Concise Method for Synthesis of 1-Acyl-4-alkoxy- or 1-Acyl-4-alkylsulfanylnaphthalene Derivatives

(Matrix presented) A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanylnaphthalenes has been developed by the reaction of o-ethynylbenzoates or benzothioates with vinyl ethers, in the presence of a catalytic amount of PtCl2. It is proposed that the reaction proceeds through [3 + 2]-cycloaddition of the platinum-containing carbonyl ylides followed by 1,2-alkyl migration.

NOVEL 2-ARYLTHIAZOLE COMPOUNDS AS PPARALPHA AND PPARGAMA AGONISTS

The present invention relates to compounds of formula (I) wherein Rl to R10, X, Y and n are as defined in the description and claims, and pharmaceutically acceptable salts and esters thereof. The compounds are useful for the treatment of diseases such as diabetes.