73790-09-7

Usage

InChI:InChI=1/C14H12O3/c1-2-17-14(16)13(15)12-8-7-10-5-3-4-6-11(10)9-12/h3-9H,2H2,1H3

Upstream product

• 91-20-3 naphthalene 
• 4755-77-5 Ethyl oxalyl chloride 
• 580-13-2 2-bromonaphthalene 
• 95-92-1 oxalic acid diethyl ester 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 939-27-5 2-ethylnaphthalene 
• 141-78-6 ethyl acetate 
• 1355333-08-2 ethyl 2-(naphthalen-2-yl)-2-nitroacetate 
• 64-17-5 ethanol 
• 93-08-3 methyl 2-naphthyl ketone 
• 7498-57-9 2-naphthaleneacetonitrile 
• 14289-45-3 2-(naphthalen-2-yl)-2-oxoacetic acid 
• 612-55-5 2-iodonaphthalene 
• 581-96-4 2-naphthylacetic acid 

Downstream Products

• 1282521-56-5 ethyl (S)-2-[bis(2-methoxyphenyloxy)phosphinyloxy]-2-(2-naphthyl)acetate 
• 1282521-67-8 ethyl (R)-2-[bis(2-methoxyphenyloxy)phosphinyloxy]-2-(2-naphthyl)acetate 
• 1422252-99-0 ethyl 2-[(4-methoxyphenyl)amino]-2-(2-naphthyl)-4-pentynoate 
• 1422253-10-8 C₂₁H₁₉NO₃ 
• 1453490-72-6 C₂₅H₂₅NO₅S 
• 1449336-22-4 C₂₁H₁₉NO₄S 
• 1613439-86-3 N-(3-(N,N-dimethylaminocarbonylphenyl))-2-(2-naphthyl)-2-oxoacetamide 

Relevant academic research and scientific papers

Electrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters

Electrochemical oxygen reduction reaction (ORR) is a powerful tool for introducing oxygen functional groups in synthetic chemistry. However, compared with the well-developed one-electron oxygen reduction process, the applications of two-electron oxygen re

Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters

A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.

General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling

A general synthesis of chiral α,α-diaryl carboxamides is developed by enantioselective cross-coupling between 2-bromo-2-aryl carboxamides and arylboronic acids, leading to a series of chiral α,α-diaryl carboxamides with various electronic properties and functionalities in moderate to excellent enantioselectivities and yields. The employment of a sterically bulky chiral P,P═O ligand L2 is critical for the reactivity and selectivity. This protocol is applied to an efficient asymmetric synthesis of a key intermediate of dopamine receptor agonist SKF 38393.

Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.

Diastereo- and Enantioselective Synthesis of Fluorine Motifs with Two Contiguous Stereogenic Centers

The synthesis of chiral fluorine containing motifs, in particular, chiral fluorine molecules with two contiguous stereogenic centers, has attracted much interest in research due to the limited number of methods available for their preparation. Herein, we report an atom-economical and highly stereoselective synthesis of chiral fluorine molecules with two contiguous stereogenic centers via azabicyclo iridium-oxazoline-phosphine-catalyzed hydrogenation of readily available vinyl fluorides. Various aromatic, aliphatic, and heterocyclic systems with a variety of functional groups were found to be compatible with the reaction and provide the highly desirable product as single diastereomers with excellent enantioselectivities.

Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters

A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

Rhodium(iii)-catalyzed C-H allylation of electron-deficient alkenes with allyl acetates

Rhodium-catalyzed C-H allylation of acrylamides with allyl acetates is reported. The use of weakly coordinating directing group resulted in high reaction efficiency, broad functionality tolerance and excellent γ-selectivity, which opens a new synthetic pathway for the access of 1,4-diene skeletons.

Cationic Ir/Me-BIPAM-catalyzed asymmetric intramolecular direct hydroarylation of α-ketoamides

Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various types of optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities (84-98 % ee). This is realized by the use of the cationic iridium complex [Ir(cod) 2](BArF4) and the chiral O-linked bidentate phosphoramidite (R,R)-Me-BIPAM. Carbon's got a brand new bond: Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities. This is realized by the use of an asymmetric cationic iridium complex formed in situ (see Scheme).