33656-65-4

Usage

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

Upstream product

• 2122-70-5 ethyl 2-(1-naphthyl)acetate 
• 91-20-3 naphthalene 
• 4755-77-5 Ethyl oxalyl chloride 
• 95-92-1 oxalic acid diethyl ester 
• 703-55-9 1-naphthylmagnesiumbromide 
• 119867-83-3 ethyl 1-naphthylglyoxylate 2,6-xylylhydrazone 
• 90-11-9 1-Bromonaphthalene 
• 1221966-42-2 ethyl 2-azido-2-(naphthalen-1-yl)acetate 
• 90-13-1 1-Chloronaphthalene 
• 64-17-5 ethanol 
• 39528-57-9 2-(naphthalen-1-carbonyl)acetonitrile 
• 1398178-90-9 2-(1-naphthyl)-2-diazoacetic acid ethyl ester 

Downstream Products

• 73790-00-8 ethyl α,α-difluoro-α-[1-(naphthyl)]acetate 
• 119867-83-3 ethyl 1-naphthylglyoxylate 2,6-xylylhydrazone 
• 73790-14-4 α,α-difluoro-1-naphthaleneacetic acid 
• 239-60-1 13H-dibenzo[a,i]fluorene 
• 2144-00-5 bis-[1]naphthylmethylene-hydrazine 
• 890-50-6 [1]naphthylmethylen-aniline 
• 66-77-3 1-naphthaldehyde 
• 6309-40-6 (+/-)-hydroxy-phenyl-(naphthyl-⁽¹⁾)-acetic acid 
• 1346947-88-3 C₂₂H₁₉NO₃S 
• 6341-56-6 2-(naphthalen-1-yl)-acrylic acid 
• 1449335-85-6 C₂₇H₂₇NO₆S 
• 1449335-86-7 C₂₇H₂₇NO₆S 
• 1449336-21-3 C₂₁H₁₉NO₄S 

Relevant academic research and scientific papers

Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide

A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

Preparation method of alpha-naphthylacetic acid

The invention relates to the technical field of organic synthesis, and provides a preparation method of alpha-naphthylacetic acid. The invention aims to solve the problem that preparation of alpha-naphthylacetic acid is not economical and environmentally friendly in the prior art. The preparation method comprises the following steps: (1) dissolving naphthalene and Lewis acid in a solvent, carryingout heating, adding oxalyl chloride monoester, and carrying out a reaction to generate alpha-acetonaphthone acid ester; and (2) adding the alpha-acetonaphthone acid ester obtained in the step (1) andhydrazine hydrate into a high-boiling-point alcohol solvent, carrying out a heating reaction, adding a strong base, continuing the heating reaction, and adjusting a pH value to an acidic state afterthe reaction is finished so as to obtain alpha-naphthylacetic acid. According to the method, naphthalene and oxalyl chloride monoester which are cheap and easy to obtain are used as raw materials, alpha-acetonaphthone acid ester is prepared under the action of Lewis acid, and then a series of reactions are performed under the action of hydrazine hydrate to generate alpha-naphthylacetic acid, so the use of highly toxic cyanide is avoided, highly toxic or foul gas is not generated in the reaction process, only one product is produced, reaction conditions are mild, yield is high and cost is low.

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.

Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

A novel method for synthesis of α-keto esters with phenyliodine(III) diacetate

A rapid and efficient synthesis of α-keto esters from β-ketonitriles using phenyliodine(III) diacetate is reported. This protocol gave α-keto esters in good yields. This is the first time to report the application of hypervalent iodine(III) reagents in the synthesis of α-keto esters. A plausible reaction mechanism is proposed.

Aryllithiums with increasing steric crowding and lipophilicity prepared from chlorides in diethyl ether. the first directly prepared room-temperature-stable dilithioarenes

A convenient procedure has been developed for the preparation of synthetically useful, room-temperature-stable aryllithiums starting from aryl chlorides and lithium metal. The method provides a route to aryllithiums which have previously not been accessible cleanly or could only be prepared by using more expensive starting materials.

Enantioselective enolate protonation in sulfamichael addition to r-substituted n-acryloyloxazolidin-2-ones with bifunctional organocatalyst

Organocatalytic conjugate addition of thiols to R-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically active molecules. 2011 American Chemical Society.

An efficient oxidation of primary azides catalyzed by copper iodide: A convenient method for the synthesis of nitriles

A wide range of primary azides have been efficiently oxidized by a catalytic amount of CuI and TBHP into their corresponding nitriles in aqueous solution. A variety of oxidizable functional groups were well tolerated under the reaction conditions, and oxidation of secondary azides furnished their corresponding ketones (see scheme; TBHP=tert-butyl hydroperoxide).