6341-60-2

Usage

InChI:InChI=1/C17H18O4/c1-3-20-16(18)15(17(19)21-4-2)14-11-7-9-12-8-5-6-10-13(12)14/h5-11,15H,3-4H2,1-2H3

Upstream product

• 62741-57-5 [1]naphthyl-oxalacetic acid diethyl ester 
• 703-55-9 1-naphthylmagnesiumbromide 
• 609-09-6 Diethyl ketomalonate 
• 2122-70-5 ethyl 2-(1-naphthyl)acetate 
• 105-58-8 Diethyl carbonate 
• 95-92-1 oxalic acid diethyl ester 
• 90-11-9 1-Bromonaphthalene 
• 105-53-3 diethyl malonate 
• 90-14-2 1-Iodonaphthalene 
• 132-75-2 naphthalen-1-ylacetonitrile 
• 86-52-2 1-Chloromethylnaphthalene 
• 7440-44-0 pyrographite 
• 623-49-4 ethyl cyanoformate 
• 86-87-3 naphth-1-yl acetic acid 

Downstream Products

• 114382-59-1 [1]naphthyl-malonic acid ethyl ester-phenyl ester 
• 123905-66-8 benzoyloxy-[1]naphthyl-malonic acid diethyl ester 

Relevant academic research and scientific papers

Unveiling p-quinone methide (QM) chemistry to synthesize bedaquiline (TMC 207) like architectures

Bedaquiline (TMC 207) is the first FDA-approved drug to combat multidrug-resistant (MDR) tuberculosis. Herein, we disclosed hydroacylation (tandem C–H activation/C–C bond formation/aromatization) catalyzed by Wilkinson catalyst on quinoline containing new para-quinone methides to simplify the construction of diverse bedaquiline analogs with reduction of steps. Direct installation of three crucial aryl rings in hydroacylation giving rise to α-disubstituted aryl ketone can provide a series of bedaquiline analogs.

A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides

Enantioenriched tertiary alkyl halides are prevalent in bioactive molecules and can serve as versatile synthetic intermediates to construct complex structures. While conventional access to these motifs often hinges on stereoselective carbon-halogen or carbon-carbon bond formation reactions, desymmetric approaches using halogenated and prochiral tetrasubstituted carbons are largely elusive in comparison. Here, we report that a suite of dinuclear zinc catalysts with a prolinol- or pipecolinol-derived tetradentate ligand can reductively desymmetrize a large collection of easily available halomalonic esters to α-halo-β-hydroxyesters. These polyfunctionalized tertiary alkyl fluorides, chlorides, and bromides proved to be useful intermediates toward fluorinated drug analogs and polyhalogenated monoterpenes. The facile intramolecular epoxidation of the chiral chloride and bromide products has also enabled expeditious access to natural products containing tertiary alcohol motifs.

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Aryltrifluoromethylative cyclization of unactivated alkenes by the use of PhICF3Cl under catalyst-free conditions

A concise and catalyst-free aryltrifluoromethylative cyclization of unactivated alkenes has been developed herein. The use of PhICF3Cl as a powerful trifluoromethylating agent allows easy transformations. A set of trifluoroethylated carbocycles and aza-hereocycles were efficiently synthesized in good yield and selectivity. A broad substrate scope, mild reaction conditions, and easy operation would make this method well-suited for applications.

Catalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation-Directed Nucleophilic Aromatic Substitution Reaction

A catalytic enantioselective nucleophilic aromatic substitution reaction which yields axially chiral biaryl derivatives in excellent yields with e.r. values of up to 97:3 has been developed. This process uses a chiral counterion to direct the addition of thiophenolate to a prochiral dichloropyrimidine by a tandem desymmetrization/kinetic resolution mechanism. The products can be derivatized to a range of atropisomeric structures without any reduction in enantioenrichment, thus offering access to unexplored chiral biaryl architectures.

Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: Preparation of valuable nitrogenated compounds

A wide range of prochiral 1, 3-diamines were first efficiently synthesized and subsequently desymmetrized by using lipase from Pseudomonas cepacia as catalyst and diallyl carbonate as alkoxycarbonylating agent. In all cases, the amino carbamates of R-configuration were recovered. Final selective cleavage of the N-allyloxycarbonyl moiety was carried out under mild reaction conditions, which demonstrates the high versatility and potential of this chemoenzymatic route as a source of intermediates in the synthesis of related optically active nitrogenated derivatives.

Copper(I)-catalyzed C-C and C-O coupling reactions using hydrazone ligands

Copper-catalyzed C-C coupling reaction of aryl iodides with diethylmalonate in toluene at 90C gave arylated malonates using 5 mol% of CuI with hydrazone 1a as a ligand in good yields under an aerobic atmosphere. We also found CuI/hydrazone 1b in toluene to be an efficient catalytic system for C-O coupling reactions of aryl bromides with phenols to give aryl ethers in good yields at 110C under an aerobic atmosphere.

Pyrimidine Non-Classical Cannabinoid Compounds and Related Methods of Use

Disclosed are compounds of the formula I: wherein R1, R2, V, W, X, Y and Z can be as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors.

Pyridine Non-Classical Cannabinoid Compounds and Related Methods of Use

wherein R1, R2, V, W, X, Y and Z can be as defined herein. The compounds can be used in the treatment of disorders mediated by the cannabinoid receptors.

Room-temperature copper-catalyzed α-arylation of malonates

An effective method in targeting α-aryl malonates is reported. In the presence of a catalytic amount of 2-picolinic acid and Cul, the coupling of aryl iodides with diethyl malonate proceeds smoothly even at room temperature. The high levels of functional group compatibility and exceptionally mild reaction conditions offer this an attractive protocol in accessing a variety of arylated malonates.