337376-51-9

Basic information

• Product Name: (1R,2R)-trans-1-Hydroxy-1,2-dihydro-2-naphthyl benzoate
• Synonyms: (1R,2R)-trans-1-Hydroxy-1,2-dihydro-2-naphthyl benzoate
• CAS NO: 337376-51-9
• Molecular Formula: C17H15O3
• Molecular Weight: 267.2992
• Mol File: 337376-51-9.mol

Chemical Properties

• Boiling Point: 448.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 13.17±0.40(Predicted)
• CAS DataBase Reference: (1R,2R)-trans-1-Hydroxy-1,2-dihydro-2-naphthyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-trans-1-Hydroxy-1,2-dihydro-2-naphthyl benzoate(337376-51-9)
• EPA Substance Registry System: (1R,2R)-trans-1-Hydroxy-1,2-dihydro-2-naphthyl benzoate(337376-51-9)

Safety Data

• Hazardous Substances Data: 337376-51-9(Hazardous Substances Data)

Upstream product

• 573-57-9 1,4-epoxy-1,4-dihydronaphthalene 
• 1863-63-4 ammonium benzoate 
• 65-85-0 benzoic acid 

Relevant articles and documents

Rhodium/zinc co-catalyzed asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids

The asymmetric ring opening reactions of oxabenzonorbornadienes with carboxylic acids are described. By using the complex of [Rh(COD)Cl]2and (S,S)-BDPP, with ZnI2as the co-catalyst, a range of aromatic acids and alkyl acids were utilized as nucleophiles to afford the corresponding chiral hydronaphthalene products with high enantioselectivities (84–94% ee). Thus, the present methodology has provides an effective synthetic method for the preparation of enantioenriched hydronaphthalenes.

Iridium-catalyzed asymmetric ring-opening of oxabicyclic alkenes with carboxylic acids

A novel iridium-catalyzed asymmetric ringopening of oxabicyclic alkenes with a variety of carboxylic acids was reported, which afforded the corresponding trans-carboxylic acids 1-hydroxy-1,2-dihydro-naphthalen-2-yl ester products in good yields with moderate enantioselectivities under mild conditions. The trans products are formed via the enantioselective cleavage of a bridgehead carbon-oxygen bond in 1 followed by SN2' nucleophilic attack by carboxylic acids. The effects of various bisphosphine ligands, Ag(I) salts, ammonium halides, bases, and solvents on the yields and enantioselectivities of the reaction were also investigated. The theoretical analysis of stability and hydrogen bond for 1-hydroxy-1,2-dihydronaphthalen-2-yl 4-chlorobenzoate 2a were performed using the density functional theory B3LYP methods. The trans-configuration of the product 2a was confirmed by X-ray diffraction analysis. A possible mechanism for the present catalytic reaction was proposed. Springer Science+Business Media New York 2013.

Hydronaphtalene compounds, prepared by a rhodium catalyzed ring opening reaction in the presence of phosphine ligand

The present invention is directed to a procedure for making an enantiomerically enriched compound containing a hydronaphthalene ring structure. The process involves reacting oxabenzonorbornadienes with nucleophiles using rhodium as a catalyst and in the p

Rhodium-catalysed asymmetric ring opening reactions with carboxylate nucleophiles

We have developed an asymmetric ring opening reaction of oxabenzonorbornadiene with carboxylate nucleophiles to generate enantiomerically enriched hydronaphthalene products containing an allylic carboxylate moiety. These reactions occur in good yield and excellent enantioselectivity (>90% ee). The allylic carboxylate functionality was found to be stable towards reaction with the rhodium catalyst under the reaction conditions. In order to obtain these results, two advancements were required. First, the use of protic additives was necessary for good reactivity. Second, the exchange of the halide ligand on the catalyst from chloride to iodide was required to obtain high ee.