13662-06-1

Usage

InChI:InChI=1/C13H12O2/c1-10(14)9-15-13-7-6-11-4-2-3-5-12(11)8-13/h2-8H,9H2,1H3

Upstream product

• 20009-28-3 naphth-2-yloxymethylacetylene 
• 875-83-2 sodium 2-naphtholate 
• 78-95-5 chloroacetone 
• 135-19-3 β-naphthol 
• 3698-15-5 2-(allyloxy)naphthalene 
• 598-31-2 1-bromoacetone 

Downstream Products

• 883-20-5 9-methylphenanthrene 

Relevant academic research and scientific papers

Discovery of oxime-bearing naphthalene derivatives as a novel structural type of Nrf2 activators

Abstract Recent studies have demonstrated that oxidative stress insult is one of major causes of tumor formation. Therefore, identify the effective anti-oxidative agents as a preventive approach to stop cancer progression has widely explored. Although, ma

Titanium tetrachloride promoted cyclodehydration of aryloxyketones: Facile synthesis of benzofurans and naphthofurans with high regioselectivity

An efficient and facile method for the synthesis of a broad series of benzofurans and naphthofurans is described. The direct intramolecular cyclodehydration of aryloxyketones in the presence of titanium tetrachloride affords the corresponding benzofurans and naphthofurans with good regioselectivity and yields.

Catalytic Wacker-type Oxidations Using Visible Light Photoredox Catalysis

A combined palladium/photoredox catalytic system for the efficient oxidation of terminal olefins to the corresponding methyl ketones is presented. The interplay of air, water, and light leads to a protocol in which the stoichiometric oxidants required for oxidative palladium catalysis are substituted with catalytic, single-electron transfer processes. Detailed mechanistic investigations revealed the role of the key components, in situ generated species, and catalysts. A broad range of substrates was examined in homogeneous as well as heterogeneous photoredox protocols, delivering the desired products in good yields.

Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones

A mimic of the Wacker process for C=O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess-Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.

Synthesis of methyl ketones from terminal olefins using PdCl 2/CrO3 system mimicking the Wacker process

An efficient synthesis of methyl ketones from terminal olefins using PdCl2/CrO3 system mimicking the Wacker process is developed. The method shows good functional groups compatibility, no aldehyde by-products and is operationally simple. CrO3 is the sole oxidant and replaces both Cu-salts and molecular oxygen, traditionally used in this process. The method holds potential for future applications in organic synthesis.

Iron(III) sulfate as terminal oxidant in the synthesis of methyl ketones via wacker oxidation

An efficient and environmentally benign method using Fe(III) sulfate as a terminal oxidant in the synthesis of methyl ketones from terminal olefins via the Wacker process is developed. The methodology offers high selectivity for a Markonikov product, shows good functional group compatibility, involves mild reaction conditions, and is operationally simple. Fe2(SO 4)3 is the sole terminal oxidant in this process. The method holds potential for future applications in organic synthesis.

Development of a catalytic platform for nucleophilic substitution: Cyclopropenone-catalyzed chlorodehydration of alcohols

Cyclopropenone makes the switch: 2,3-Bis-(p-methoxyphenyl)cyclopropenone is a highly efficient catalyst for the chlorodehydration of 20 diverse alcohol substrates (see scheme; X=Cl). With oxalyl chloride as catalytic activator, this nucleophilic substitution proceeded through cyclopropenium-activated intermediates and resulted in complete stereochemical inversion in substrates with chiral centers.

A study of Pd(II) Cl2/CuCl catalysed Wacker reaction for the deprotection of prop-2-enyl and prop-1-enyl ethers

Pd(II)Cl2 (1 mole equivalent)/CuCl/DMF-H2O/O2/2h catalysed oxidation of various prop-2-enyl ethers 1a-12a is reported to result in the formation of Wacker ketones 1b,3b,5b,6b,9b,11b,12b (12-51%), hydrolysis products 2c,4c-7c,9c-12c (12-43%) and η2-vinyl complexes of palladium chloride 2c,4c,7c,8c (52-94%) respectively. The corresponding prop-1-enyl ethers 2e,4e-12e under similar conditions react with a catalytic amount of Pd(II)Cl2 (0.2 mole equivalent) rapidly (15-20 min.) to give exclusively hydroxy compounds 2c,4c-12c respectively in good yields (75-97%).

Formation of ketones from alkyl nitrites in the solid state

Alkyl nitrites selectively afforded the corresponding ketones upon photoirradiation in the solid state. It was suggested by the X-ray crystallographic analysis that the cavity in crystal and the initial conformation of the nitroso group had an influence on the yield of the ketones.

POLYMER-SUPPORTED REAGENTS: AN EFFICIENT METHOD FOR THE SYNTHESIS OF PHENOXYACETONES

Phenoxides supported on Amberlite IRA-400 reacted with chloroacetone to give the corresponding phenoxyacetones in high yields and purity.