947-62-6

Usage

Uses

2-Methoxy-1-naphthoic acid may be used in the synthesis of chiral (methoxynaphthyl)oxazoline.

General Description

2-Methoxy-1-naphthoic acid is the 3-methoxy derivative of 1-napthoic acid. It can be prepared from a Grignard reagent derived from 1-bromo-2-methoxynaphthalene. 2-Methoxy-1-naphthoic acid undergoes Birch reduction to afford 2-methoxy-1,4,5,8-tetrahydro-1-naphthoic acid.

InChI:InChI=1/C12H10O3/c1-15-10-7-6-8-4-2-3-5-9(8)11(10)12(13)14/h2-7H,1H3,(H,13,14)

Upstream product

• 109-72-8 n-butyllithium 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 5392-12-1 2-methoxy-1-naphthaldehyde 
• 15719-64-9 methylammonium carbonate 
• 77-78-1 dimethyl sulfate 
• 2283-08-1 2-hydroxy-1-naphthalenecarboxylic acid 
• 15219-34-8 Oxalyl bromide 
• 93-04-9 2-Methoxynaphthalene 
• 13343-92-5 methyl ester of 2-methoxy-1-naphthalenecarboxylic acid 
• 93137-91-8 2-Methoxy-naphthoyl-⁽¹⁾-cyanid 
• 141-82-2 malonic acid 
• 124-38-9 carbon dioxide 
• 32721-21-4 1-iodo-2-methoxynapthalene 
• 74-88-4 methyl iodide 

Downstream Products

• 13343-92-5 methyl ester of 2-methoxy-1-naphthalenecarboxylic acid 
• 51439-58-8 2-methoxy-1-naphthoic acid chloride 
• 818375-08-5 2-methoxy-1-naphthyl (2-acetamido-4,6-dimethoxy)phenyl ketone 
• 824960-76-1 (2-methoxy-1-naphthalenyl)(1-pentyl-1H-indol-3-yl)methanone 
• 2246-42-6 2-methoxynaphthylamine 
• 137869-22-8 2-phenyl-1-naphthaldehyde 
• 137869-15-9 2-(2-phenyl-1-naphthyl)oxazoline 
• 137869-18-2 2-<2-(O-methylephedrinyl)-1-naphthyl>oxazoline 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 16000-39-8 1-cyano-2-methoxynaphthalene 
• 855261-19-7 [2,2'-binaphthalene]-1-carboxylic acid 
• 108981-94-8 2-phenyl-1-naphthalenecarboxylic acid 
• 13101-92-3 1-chloro-2-methoxynaphthalene 

Relevant academic research and scientific papers

6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline amides and corresponding ester isosteres as multidrug resistance reversers

Aiming to deepen the structure–activity relationships of the two P-glycoprotein (P-gp) modulators elacridar and tariquidar, a new series of amide and ester derivatives carrying a 6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline scaffold linked to different methoxy-substituted aryl moieties were synthesised. The obtained compounds were evaluated for their P-gp interaction profile and selectivity towards the two other ABC transporters, multidrug-resistance-associated protein-1 and breast cancer resistance protein, showing to be very active and selective versus P-gp. Two amide derivatives, displaying the best P-gp activity, were tested in co-administration with the antineoplastic drug doxorubicin in different cancer cell lines, showing a significant sensitising activity towards doxorubicin. The investigation on the chemical stability of the derivatives towards spontaneous or enzymatic hydrolysis, showed that amides are stable in both models while some ester compounds were hydrolysed in human plasma. This study allowed us to identify two chemosensitizers that behave as non-transported substrates and are characterised by different selectivity profiles.

Naphthyl, (substituted) aryl, piperazine base trunk apperception composition

The invention discloses (substituted) naphthyl, (substituted) aryl, piperazinyl amidine compound with new structures and salt of medical acid, a preparation method and a purification method of the compound and the salt of the medical acid, and a medicine composition containing the compound, wherein the compound has double inhibition activities of 5-hydroxytryptamine (5-HT) reuptake and noradrenalin (NE) reuptake, and shows strong depression resistance in animal experiments. The compound can be used for treating tristimania, and can also be used for treating other nervous system diseases related to the 5-HT and the NE.

Decarbonylative halogenation by a vanadium complex

Metal-catalyzed halogenation of the C-H bond and decarbonylation of aldehyde are conventionally done in nature. However, metal-mediated decarbonylative halogenation is unknown. We have developed the first metal-mediated decarbonylative halogenation reaction starting from the divanadium oxoperoxo complex K3V5+2(O 22-)4(O2-)2(μ-OH) (1). A concerted decarbonylative halogenation reaction was proposed based on experimental observations.

Aryllithiums with increasing steric crowding and lipophilicity prepared from chlorides in diethyl ether. the first directly prepared room-temperature-stable dilithioarenes

A convenient procedure has been developed for the preparation of synthetically useful, room-temperature-stable aryllithiums starting from aryl chlorides and lithium metal. The method provides a route to aryllithiums which have previously not been accessible cleanly or could only be prepared by using more expensive starting materials.

Metalation of 2-heterosubstituted naphthalenes at the 1- or 3- position: Factors that may determine the regiochemistry

Upon metalation and subsequent electrophilic trapping, 2-fluoronaphthalene inevitably gives rise to regioisomeric mixtures in varying proportions, whereas 2-(trifluoromethyl)naphthalene undergoes deprotonation either at the 1- or the 3-position, depending on the choice of the reagent. On the other hand, 2-(trifluo-romethoxy)naphthalene and 2-methoxynaphthalene react exclusively at the 3-position when, respectively, sec-butylhthium and superbasic reagents are employed. Steric repulsion by the peri hydrogen in combination with crowding due to coordination of the lithium atom with the methoxy group disfavors attack at the 1-position. Georg Thieme Verlag Stuttgart.

Benzo[a]pyrano[3,2-h]acridin-7-one compounds

A compound selected from those of formula (I): 1 wherein: X and Y represent a group selected from hydrogen, halogen, hydroxy, alkoxy, nitro, cyano, alkyl, trihaloalkyl and NRaRb, wherein Ra and Rb are as defined in the description R1 represents hydrogen or alkyl R2 represents a group selected from hydrogen, alkyl, —OR″a, —NR′aR′b, -Ta-O″a, —N″a-Ta-NR′aR′b, —N″a—C(O)-TaH, —O—C(O) TaH, Ta-NR′aR′b, —NR″a-Ta-OR″a, —NR″a-Ta-CO2R″a and —N″a—C(O)-Ta-NR′aR′b, wherein R′a, R″a, R′b and Ta are as defined in the description R3 and R4 represent hydrogen or alkyl A represents a group of formula —CH(R5)CH(R6), —CH=C(R7)—, —C(R7)=CH—, —C(O)CH(R8) or —CH(R8)—C(O), wherein R5, R6, R7 and R8 are as defined in the description its isomers, N-oxides, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.

Behavior of naphthoyloxyl and methoxynaphthoyloxyl radicals generated from the photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones

1-Naphthoyloxyl and 2-naphthoyloxyl radicals were generated from photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones in acetonitrile. The difference in product distribution between the precursors is ascribed to the contribution of the two-bond cleavage in the peroxide decomposition in the singlet state. A series of methoxynaphthoyloxyl radicals were also generated from the corresponding (methoxynaphthoyloxy)pyridones and their behavior was compared with that of unsubstituted naphthoyloxyl radicals. The introduction of a methoxy group in the naphthalene ring stabilizes the naphthoyloxyl radicals to prevent their decarboxylation completely and reduces remarkably their reactivities in the addition to olefins and hydrogen-atom abstraction. The structure of the naphthoyloxyl radicals was discussed on the basis of their absorption spectra and MO calculations.

Barriers to rotation about the chiral axis of tertiary aromatic amides

The barrier to rotation about the aryl-carbonyl bond in 40 tertiary aromatic amides was determined by variable temperature NMR spectroscopy (for rapid rotations) or by following the interconversion of atropisomers (for slower rotations). Empirical guidelines to the rate of Ar-CO bond rotation in hindered tertiary aromatic amides, and hence the stability of the atropisomeric stereoisomers of axially chiral amides, are presented.

Regiospecific synthesis of polysubstituted naphthalenes via oxazoline-mediated nucleophilic aromatic substitutions and additions

An efficient procedure for the selective functionalization of several positions of 2-methoxynaphthalene is described. Nucleophilic aromatic substitutions were carried out by displacing both a methoxy group and a neutral amine ortho to an oxazoline 6. 4-Substituted naphthalenes 8 were obtained from nucleophilic aromatic addition of an allyllithium species to a position para to the oxazoline 6. The resultant dihydronaphthalenes were converted to the fully aromatic systems 9 or alternatively substituted in the 2-position to form 10. Reductive cleavage of the oxazoline moities in 7 and 9 proceeded smoothly, producing the substituted naphthaldehydes 11.

Oxidation of Malonic Acid Derivatives by Manganese(III) Acetate. Aromatic Malonylation Reaction. Scope and Limitations

The oxidation of malonic acid derivatives RCH(COOR1)COOR2 (R1 = or R2 = H, Me, Et; R = H, Me, Et, n-Bu, i-Pr, C6H5, 4-OMeC6H4) by anhydrous or dihydrated manganese(III) acetate was studied in acetic acid in the presence of aromatic substrates at 20-80 deg C, generally with stoichiometric amounts of reagents.Electron-rich aromatics (IP 7.5 eV) underwent nuclear acetoxylation or quinone formation, the process being exclusive with anthracene and competitive with nuclear malonylation for 1- and 2-methoxynaphthalene.With other less electron-rich substrates (IP 8.5 eV) only the products coming from the oxidation of the malonic acid derivatives (aryl malonates, tartronates, etc., or dimerization and disproportionation products) were observed.The selectivity and the yield of aromatic substitution by the malonyl group was found to be affected by the electron density of the aromatic ring, the steric inhibition of substituents in the Mn(III) oxidation of the malonic acid derivative, the oxidizability of malonyl radical by Mn(III), the base (acetate ions or water) eventually present in the medium, and the further easy oxidation of the primary aryl malonate product, when unsubstituted dialkylmalonates or malonic acid were used.A mechanism is suggested in which inner-sphere electron transfer from Mn(III)-malonate complex affords Mn(II) malonyl radicals that are partitioned between oxidation, dimerization (or disproportionation), and reversible addition to the aromatics.