72775-28-1

Usage

Class

Organic compounds

Subclass

Methoxy-naphthalenes

Derivation

Derived from naphthalene by adding a methoxy group at the 7-position and an acetyl group at the 2-position

Applications

a. Synthesis of other chemical compounds
b. Flavoring agent in the food industry
c. Production of fragrances and perfumes due to its pleasant odor
d. Pharmaceutical industry as an intermediate for the synthesis of pharmaceutical drugs

InChI:InChI=1/C13H12O2/c1-9(14)11-4-3-10-5-6-13(15-2)8-12(10)7-11/h3-8H,1-2H3

Upstream product

• 72775-33-8 1-(2-<7-Methoxy>naphthyl)ethanol 
• 135653-94-0 7-methoxy-2-trifluoromethanesulfonyloxynaphthalene 
• 72775-47-4 3,4-Dihydro-7-methoxy-2-naphthalincarbonsaeureethylester 
• 72775-48-5 7-methoxynaphthalene-2-carboxylic acid ethyl ester 
• 5043-07-2 7-methoxy-naphthalen-2-carboxylic acid 

Relevant academic research and scientific papers

Fast and regioselective Heck couplings with N-acyl-N-vinylamine derivatives

Highly regioselective Heck couplings of aryl inflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd2(dba)3, 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph 3P)3RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the α-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

Palladium-catalyzed aerobic oxidative kinetic resolution of alcohols with an achiral exogenous base

Substitution of exogenous (-)-sparteine for a more practical achiral base in the aerobic oxidative kinetic resolution of secondary alcohols is described. Carbonate bases are the most effective of those screened and allow for effective kinetic resolution of benzylic, allylic, and aliphatic substrates. The procedure was also successfully extended to the oxidative desymmetrization of meso diols.