18515-11-2

Usage

Uses

Used in Pharmaceutical Industry:
3-METHOXY-2-NAPHTHOL 97 is used as a key intermediate in the synthesis of various pharmaceutical compounds. One of its primary applications is in the production of a naphthoate ester, which acts as a dopamine D4 antagonist. This makes it a valuable compound in the development of drugs targeting dopamine-related disorders, such as schizophrenia and Parkinson's disease.
Used in Chemical Synthesis:
In the field of organic chemistry, 3-METHOXY-2-NAPHTHOL 97 serves as a versatile building block for the synthesis of a wide range of chemical compounds. Its reactivity allows for various functional group transformations, making it a useful starting material for the creation of novel molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Dye and Pigment Industry:
3-METHOXY-2-NAPHTHOL 97 can also be utilized in the production of dyes and pigments due to its ability to form colored compounds. Its chemical structure allows for the creation of a diverse range of colors, making it a valuable component in the formulation of dyes and pigments for various applications, such as textiles, plastics, and printing inks.

InChI:InChI=1/C11H10O2/c1-13-11-7-9-5-3-2-4-8(9)6-10(11)12/h2-7,12H,1H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 92-44-4 2,3-naphthalenediol 
• 471248-33-6 C₁₁H₁₂O₃ 
• 10103-06-7 2,3-dimethoxynaphthalene 
• 104115-76-6 3-methoxynaphthalen-2-ylboronic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 18515-12-3 3,3'-dimethoxy-1,1'-binaphthyl-2,2'-diol 
• 47644-69-9 dimethyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate 
• 128702-26-1 Methyl 3'-methoxy-2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate 
• 35152-99-9 N-Acetyl-3,5-dinitro-L-tyrosinaethylester-3'-methoxy-2'naphthylaether 
• 850533-42-5 (2S,3S,4R)-2-(Diphenyl-phosphinoylmethyl)-4-(3-methoxy-naphthalen-2-yloxy)-tetrahydro-pyran-3-ol 
• 170889-47-1 diphenyl 2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxylate 
• 753022-44-5 2-(2-tosyloxyethoxy)-3-methoxynaphthalene 
• 776332-06-0 C₄₆H₄₄O₈ 
• 776332-13-9 C₆₀H₅₈O₁₁ 
• 75965-72-9 nitro-2 methoxy-4 naphto<2,1-b>furanne 
• 35153-07-2 N-Acetyl-3,5-diiod-L-tyrosinaethylester-3'-methoxy-2'-naphthylaether 
• 5892-01-3 3-Methoxy-1,2-naphthalindiol 
• 1226970-66-6 3-(hydroxymethyl)-1-((1S,3R)-3-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl)naphthalen-2-ol 
• 1446145-70-5 1-(5-bromo-2-hydroxy-3-methoxyphenyl)-3-methoxynaphthalen-2-ol 

Relevant academic research and scientific papers

Sulfonation of a series of naphthalenes containing two different oxy substituents

The reactions of a series of α,α- and β,β-disubstituted naphthalenes containing two different substituents OR1 (R1 = H, SO2CH3) and OR2 (R2 =CH3, SO2CH3) with sulfur trioxide in CD3NO2 has been studied.The electronic directing effect of the hydroxy group was found to be dominant over that of the methoxy group, which in turn dominates that of the mesyloxy group.Upon reaction with an excess of sulfur trioxide, the hydroxy group is, at least in part, sulfated.For the β-hydroxy-β-methoxynaphthalenes 3a-5a and for 3-mesyloxy-2-naphthol (3c) especially, hydrogen sulfate formation strongly influences the product mixture composition.Thus, upon reaction with 1.0 equiv of SO3, 7-methoxy-2-naphthol (5a) yields its 1-sulfonic acid (1-S), whereas upon reaction with 2.0 equiv, it is the 8-S that is mainly formed due to initial hydrogen sulfate formation.Furthermore, sulfonic acid isomerizations due to steric hindrance are observed.Upon using >2.0 equiv of SO3, formation of di- and trisulfonic acids, as well as sulfo derivatives of both 8,1-naphthalenesultone and the cyclic naphthalene-1-sulfonate-2-sulfate anhydride is observed.

ION CHANNEL ANTAGONISTS/BLOCKERS AND USES THEREOF

Provided are ion channel antagonists/blockers and uses thereof. Specifically, it provides the compounds of formula (I) or pharmaceutically acceptable salts, stereoisomers, solvates or prodrugs, preparation method therefor and application thereof. Definition of each group in the formula can be found in the specification for details. Provided is also pharmaceutical composition useful for treatment of heart disease and other ion channel related diseases.

Oxygen-Free Regioselective Biocatalytic Demethylation of Methyl-phenyl Ethers via Methyltransfer Employing Veratrol- O-demethylase

The cleavage of aryl methyl ethers is a common reaction in chemistry requiring rather harsh conditions; consequently, it is prone to undesired reactions and lacks regioselectivity. Nevertheless, O-demethylation of aryl methyl ethers is a tool to valorize natural and pharmaceutical compounds by deprotecting reactive hydroxyl moieties. Various oxidative enzymes are known to catalyze this reaction at the expense of molecular oxygen, which may lead in the case of phenols/catechols to undesired side reactions (e.g., oxidation, polymerization). Here an oxygen-independent demethylation via methyl transfer is presented employing a cobalamin-dependent veratrol-O-demethylase (vdmB). The biocatalytic demethylation transforms a variety of aryl methyl ethers with two functional methoxy moieties either in 1,2-position or in 1,3-position. Biocatalytic reactions enabled, for instance, the regioselective monodemethylation of substituted 3,4-dimethoxy phenol as well as the monodemethylation of 1,3,5-trimethoxybenzene. The methyltransferase vdmB was also successfully applied for the regioselective demethylation of natural compounds such as papaverine and rac-yatein. The approach presented here represents an alternative to chemical and enzymatic demethylation concepts and allows performing regioselective demethylation in the absence of oxygen under mild conditions, representing a valuable extension of the synthetic repertoire to modify pharmaceuticals and diversify natural products.

Vinylene-Bridged Two-Dimensional Covalent Organic Frameworks via Knoevenagel Condensation of Tricyanomesitylene

Vinylene-bridged covalent organic frameworks (COFs) have shown great potential for advanced applications because of their high chemical stability and intriguing semiconducting properties. Exploring new functional monomers available for the reticulation of vinylene-bridged COFs and establishing effective reaction conditions are extremely desired for enlarging the realm of this kind of material. In this work, a series of vinylene-bridged two-dimensional (2D) COFs are synthesized by Knoevenagel condensation of tricyanomesitylene with ditopic or tritopic aromatic aldehydes. With use of appropriate secondary amines as catalysts, high-crystalline vinylene-bridged COFs were achieved, exhibiting long-range ordered structures, well-defined nanochannels, high surface areas (up to 1231 m2 g-1), and excellent photophysical properties. Under a low loading amount and short reaction time, they enable aerobic photocatalytic transformation of arylboronic acids to phenols with high efficiency and excellent recyclability. This work demonstrates a new functional monomer, tricyanomesitylene, feasible for the general synthesis of vinylene-bridged COFs with potential application in photocatalytic organic transformation, which instigates further research on such kind of material.

Enantioselective iron/bisquinolyldiamine ligand‐catalyzed oxidative coupling reaction of 2‐naphthols

An iron‐catalyzed asymmetric oxidative homo‐coupling of 2‐naphthols for the synthesis of 1,1′‐Bi‐2‐naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron‐complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)‐N1,N2‐di(quinolin‐8‐yl)cyclohexane‐1,2‐diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.

Efficient anodic and direct phenol-arene C,C cross-coupling: The benign role of water or methanol

C,C cross-coupling reactions for the synthesis of nonsymmetrical biaryls represent one of the most significant transformations in contemporary organic chemistry. A variety of useful synthetic methods have been developed in recent decades, since nonsymmetrical biaryls play an evident role in natural product synthesis, as ligand systems in homogeneous catalysis and materials science. Transformation of simple arenes by direct C,H activation belongs to the cutting-edge strategies for creating biaryls; in particular the 2-fold C,H activation is of significant interest. However, in most examples very costly noble metal catalysts, ligand systems, and significant amount of waste-producing oxidants are required. Electrochemical procedures are considered as inherently "green" methods, because only electrons are required and therefore, no reagent waste is produced. Here, we report a metal-free electrochemical method for cross-coupling between phenols and arenes using boron-doped diamond (BDD) anodes in fluorinated media. Our sustainable approach requires no leaving functionalities. Employing water or methanol as mediator represents the key improvement for achieving nonsymmetrical biaryls with superb selectivity and synthetic attractive yields.

Acid-catalyzed dehydration of naphthalene-cis-1,2-dihydrodiols: Origin of impaired resonance effect of 3-substituents

Acid-catalyzed dehydrations of substituted naphthalene-cis-1,2-dihydrodiols occur with loss of the 1- or 2-OH group to form 2- and 1-naphthols, respectively. Effects of substituents MeO, Me, H, F, Br, I, and CN at 3-, 6-, and 7-positions of the naphthalene ring are consistent with rate-determining formation of β-hydroxynaphthalenium ion (carbocation) intermediates. For reaction of the 1-hydroxyl group the 3-substituents are correlated by the Yukawa-Tsuno relationship with ρ = -4.7 and r = 0.25 or by σp constants with ρ = -4.25; for reaction of the 2-hydroxyl group the 3-substituents are correlated by σm constants with ρ = -8.1. The correlations for the 1-hydroxyl imply a surprisingly weak resonance interaction of +M substituents (MeO, Me) with a carbocation reaction center but are consistent with the corresponding correlation for acid-catalyzed dehydration of 3-substituted benzene-cis-1,2-dihydrodiols for which ρ = -6.9 and r = 0.43. Substituents at the 6- and 7-positions of the naphthalene rings by contrast are correlated by σ+ with ρ = -3.2 for reaction of the 1-hydroxyl group and ρ = -2.7 for reaction of the 2-hydroxyl group. The unimpaired resonance implied by these substituent effects appears to be inconsistent with a previous explanation of the weak resonance of the 3-substituents in terms of imbalance of charge development and/or nonplanarity of the benzenium ring in the transition state. An alternative possibility is that the adjacent hydroxyl group interferes sterically with conjugation of +M substituents. "Hyperaromaticity" of the arenium ion intermediates does not appear to be a factor influencing this behavior.

Structure-affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the α1a-AR with respect to the other two α1 subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific α1a affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high α1a affinity of (S)-1 and its α1a versus α1b selectivity slightly increasing the α1a/α1d and α1a/5HT 1A affinity ratios. The SAR data were evaluated in the light of known α1 subtype pharmacophores and of the α1a-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models.

Derivatives of naphthalene with comt inhibiting activity

Compounds of formula (I′), wherein A, R1 to R3 and t are as defined in the disclosure, exhibit COMT enzyme inhibiting activity so that they are useful as COMT inhibitors.