138604-66-7

Basic information

• Product Name: (1R)-menthyl (aS,1R)-2’-methoxy-(1,1’-binaphthyl)-2-carboxylate
• Synonyms: (1R)-menthyl (aS,1R)-2’-methoxy-(1,1’-binaphthyl)-2-carboxylate
• CAS NO: 138604-66-7
• Molecular Weight: 466.62
• Mol File: 138604-66-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (1R)-menthyl (aS,1R)-2’-methoxy-(1,1’-binaphthyl)-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-menthyl (aS,1R)-2’-methoxy-(1,1’-binaphthyl)-2-carboxylate(138604-66-7)
• EPA Substance Registry System: (1R)-menthyl (aS,1R)-2’-methoxy-(1,1’-binaphthyl)-2-carboxylate(138604-66-7)

Safety Data

• Hazardous Substances Data: 138604-66-7(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 116741-62-9 (aS)-2'-methoxy-1,1'-binaphthyl-2-carbonyl chloride 
• 80317-69-7 2’-methoxy-(1,1’-binaphthyl)-2-carboxylic acid 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 129656-73-1 (-)-menthyl 1-(-)-menthyloxy-2-naphthoate 
• 36321-90-1 2-methoxy-1-naphthylmagnesium bromide 
• 93-04-9 2-Methoxynaphthalene 
• 127721-17-9 l-p-menth-3-yl 1-methoxy-2-naphthoate 
• 6039-59-4 methyl 1-methoxy-2-naphthoate 
• 86-48-6 1-hydroxy-2-naphthoic acid 

Relevant articles and documents

Axially Chiral 1,1'-Binaphthyl-2-Carboxylic Acid (BINA-Cox) as Ligands for Titanium-Catalyzed Asymmetric Hydroalkoxylation

Axially chiral, enantiopure 1,1'-binaphthyl-2-carboxylic acids (BINA-Cox) have recently been introduced as chiral ligands for transition metal catalysis. Together with equimolar, co-catalytic amounts of Ti(OiPr)4 and water they form an in situ catalyst that performs the asymmetric catalytic hydroalkoxylation of 2-allylphenols to 2-methylcoumarans at high temperature (240 °C, microwave heating). The synthesis of reference ligand 2'-MeO-BINA-Cox (L1) has been optimized and performed at molar scale. Synthetic routes have been developed to access a variety of substituted BINA-Cox ligands (>30 examples), which have been tested for ligand effects on the reference asymmetric cyclization of 2-allylphenol. The substrate range of asymmetric catalytic hydroalkoxylation has been explored through systematic substrate structure variations to define scope and limitations of the titanium-catalyzed process. The new substrates 2-(1-vinylcycloalkyl)phenols (1j, 1k), 2-(2-vinylphenyl)propan-2-ol (1t), and 2'-vinyl-[1,1'-biphenyl]-2-ol (1u) are shown to undergo asymmetric catalytic cyclization to benzodihydrofurans and benzo[c]chromene, respectively.

Asymmetric synthesis of helical poly(quinoxaline-2,3-diyl)s by palladium-mediated polymerization of 1,2-diisocyanobenzenes: Effective control of the screw-sense by a binaphthyl group at the chain-end

Aromatizing polymerization of 1,2-diisocyanobenzene derivatives was mediated by optically active organopalladium(II) complexes bearing 1,1'- binaphth-2-yl groups to give optically active poly(quinoxaline-2,3-diyl)s with varying screw-sense selectivities, which crucially depended upon the substituents on the binaphthyl groups. The most effective catalyst, which has 7'-methoxy-1,1'-binaphthyl group, induced the formation of a single screw- sense. Isolation and structural analyses (single-crystal X-ray diffraction and 1H NMR spectroscopy) of intermediary [oligo(quinoxalinyl)]palladium complexes revealed that the screw-sense selection in the polymerization may be decisively governed by the diastereomeric ratios of the (terquinoxalinyl)palladium(II) complex intermediate.

An Efficient Asymmetric Synthesis of Atropisomeric 1,1'-Binaphthyls via Nucleophilic Aromatic Substitution Reaction

High levels of asymmetric induction (up to 98percent optical yield) were achieved in the joining of two naphthalene rings by the nucleophilic displacement of 1-menthoxyl group of 1-(-)-menthoxy-2-naphthoates (1) with 1-naphthyl Grignard reagents.Also repo