26593-50-0

Usage

Purification Methods

Crystallise the naphthol from EtOH or ligroin. It has m 118o after sublimation in vacuo. [Halsall & Thomas J Chem Soc 2564 1956, Beilstein 6 IV 3029.]

InChI:InChI=1/C11H10O/c1-8-2-3-9-4-5-11(12)7-10(9)6-8/h2-7,12H,1H3

Upstream product

• 1131-53-9 2-methoxy-7-methylnaphthalene 
• 6836-19-7 7-Methoxy-1-tetralone 
• 61582-84-1 3,4-dihydro-7-methoxy-2-methylnaphthalen-1(2H)-one 
• 5060-82-2 7-methoxy-2-naphthol 
• 75-24-1 trimethylaluminum 
• 116230-30-9 7-bromonaphthalen-2-ol 
• 74-88-4 methyl iodide 
• 75-16-1 methylmagnesium bromide 
• 676-58-4 methylmagnesium chloride 
• 199442-39-2 1-hydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene 
• 127926-10-7 (+)-cis-1,2-dihydro-(1R,2S)-dihydroxy-7-methylnaphthalene 
• 152461-47-7 methyl-(7-methyl-5,6,7,8-tetrahydro-[2]naphthyl)-ether 
• 117356-92-0 N-benzyl-(1-hydroxy-1,2,3,4-tetrahydro-7-methoxynaphthalene-2-methyl)amine 
• 117356-91-9 N-benzyl-(1,2,3,4-tetrahydro-7-methoxy-1-oxonaphthalene-2-methyl)amine 

Downstream Products

• 398-65-2 (4-fluoro-phenyl)-(7-methyl-[2]naphthyl)-amine 
• 186550-85-6 7-methylnaphthalene-2-sulfonyl chloride 
• 186550-86-7 7-Methyl-naphthalene-2-sulfonic acid [(S)-1-(3-cyano-benzyl)-2-oxo-pyrrolidin-3-yl]-amide 
• 116530-25-7 7-methylnaphthalen-2-amine 

Relevant academic research and scientific papers

Method for resolving chiral compound

The invention relates to the field of organic chemistry, in particular to a method for resolving a chiral compound. The method for splitting the chiral compound provided by the invention comprises thestep of carrying out addition reaction on a racemic compound shown as a formula A and azodicarbonic acid ester in the presence of a catalyst so as to provide an S-configuration compound shown as theformula A and an S-configuration compound shown as the formula C. According to the method, chiral phosphoric acid is used as a catalyst; good catalytic effect is achieved, and very wide substrate applicability is also achieved; the product and the recovered raw material can be obtained with excellent enantioselectivity, the selectivity coefficient of kinetic resolution can reach 371, and the method has an excellent kinetic resolution effect on various N-monosubstituted and N-unsubstituted binaphthalene diamines, H8-binaphthalene diamines and biphenyl diamines.

Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-Quinones: Platform Molecules for Diversity-Oriented Synthesis of Biaryldiols

Presented here is a class of novel axially chiral aryl-p-quinones as platform molecules for the preparation of non-C2 symmetric biaryldiols. Two sets of aryl-p-quinone frameworks were synthesized with remarkable enantiocontrol by means of chiral phosphoric acid catalyzed enantioselective arylation of p-quinones by central-to-axial chirality conversion. These aryl-p-quinones were then used to access a wide spectrum of highly functionalized non-C2 symmetric biaryldiols with excellent retention of the enantiopurity.

Transition-Metal-Free Aryl–Aryl Cross-Coupling: C?H Arylation of 2-Naphthols with Diaryliodonium Salts

Transition-metal-free regioselecitive C?H arylation of 2-naphthols with diaryliodonium salts has been developed. The reaction proceeds under very simple experimental conditions and affords a range of products with various substitution patterns. The method allows for the incorporation of electron-deficient aryls, which complements well currently existing metal-free aryl–aryl cross-couplings of phenols that have been so far restricted to the introduction of electron-rich aryl moieties. The mechanism of the reaction was studied by means of DFT calculations, demonstrating that the C?C bond formation occurs via a dearomatization of 2-naphthol substrate, followed by a subsequent rearomatization by tautomerization. The computations show that the use of a low polarity solvent and an insoluble inorganic base is key to securing the high selectivity of the C?C coupling over a competing C?O arylation pathway, by preventing the incipient deprotonation of 2-naphthol.

Deleterious effect of 7-methyl group on glycosylation of 2-naphthols

C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (1). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-napht

Nickel-catalyzed cross-coupling of anisole derivatives with trimethylaluminum through the cleavage of carbonoxygen bonds

Nickel-catalyzed cross-coupling of methoxyarenes with trimethylaluminum is described. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand and NaO'Bu as a base promotes the methylation of anisole derivatives via the cleavage of normally unreactive aryl carbonoxygen bonds.

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.

Design and structure-activity relationships of potent and selective inhibitors of blood coagulation factor Xa

The discovery of a series of non-peptide factor Xa (FXa) inhibitors incorporating 3-(s)-amino-2-pyrrolidinone as a central template is described. After identifying compound 4, improvements in in vitro potency involved modifications of the liphophilic group and optimizing the angle of presentation of the amidine group to the S1 pocket of FXa. These studies ultimately led to compound RPR120844, a potent inhibitor of FXa (K1 = 7 nM) which shows selectivity for FXa over trypsin, thrombin, and several fibrinolytic serine proteinases. RPR120844 is an effective anticoagulant in both the rat model of FeCl2-induced carotid artery thrombosis and the rabbit model of jugular vein thrombus formation.

Excited-State Proton-Transfer Kinetics: A Theoretical Model

The intersecting-state model is applied to excited state proton-transfer reactions.The results are consistent with those previously obtained for the analogous ground-state reactions.The transition-state bond order n* is similar in the ground and excited states: carbon acids have lower n* than nitrogen or oxygen acids.The mixing entropy parameter λ is found to be lower for excited-state than ground-state reactions.The mechanistic implications of this are discussed.