3183-15-1

Upstream product

• 82084-26-2 5-Benzyl-2,3-dihydro-furan 
• 103-80-0 phenylacetyl chloride 
• 140-29-4 phenylacetonitrile 
• 123-25-1 succinic acid diethyl ester 
• 3350-92-3 5-phenylpent-4-ynoic acid 
• 25684-06-4 2-hydroxy-3-(benzyl)-2-cyclopenten-1-one 
• 5747-06-8 4-phenylpent-4-enoic acid 
• 102-04-5 1,3-Diphenylpropanone 
• 6921-34-2 benzylmagnesium chloride 
• 59092-50-1 β-(1-chlorovinyl)-β-propiolactone 
• 7732-18-5 water 
• 66049-99-8 benzyl-5-(5H)furannone-2 
• 7664-93-9 sulfuric acid 
• 42464-63-1 (E)-2-benzylidene-1-methylpyrrolidin-5-one 

Downstream Products

• 3183-16-2 α-Benzylglutaminsaeure 
• 924893-94-7 (S)-4-hydroxy-N,N-dimethyl-5-phenylpentanamide 
• 1380503-45-6 (S)-4-(dimethylcarbamoyl)-1-phenyl-2-butyl acetate 
• 415902-37-3 (S)-5-benzyl-dihydrofuran-2(3H)-one 
• 437606-63-8 (R)-5-phenyl-γ-valerolactone 
• 1380503-44-5 4-(dimethylcarbamoyl)-1-phenyl-2-butyl acetate 
• 1380503-46-7 (R)-4-hydroxy-N,N-dimethyl-5-phenylpentanamide 
• 122715-97-3 N,N-dimethyl-4-oxo-5-phenylpentaneamide 
• 449777-85-9 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-D-glucal 
• 1444311-57-2 2-[3-benzyl-5-(4-methoxybenzyl)-6-oxopyridazin-1(6H)-yl]acetic acid 
• 1444311-41-4 ethyl 2-[3-benzyl-5-(4-methoxybenzyl)-6-oxopyridazin-1(6H)-yl]acetate 
• 1444311-25-4 6-benzyl-4-(4-methoxybenzyl)pyridazin-3(2H)-one 
• 127478-19-7 4,5-dihydro-6-benzylpyridazine-3(2H)-one 
• 928215-55-8 4-oxo-5-phenylpentan-N-phenylamide 

Relevant academic research and scientific papers

Novel lactonization with phenonium ion participation induced by hypervalent iodine reagents

(Matrix presented) A novel lactonization of 4-aryl-4-pentenoic acids is described using aryl-λ3-iodanes as reagents for this transformation. The hypervalent iodine species acts as a hypernucleofuge, generating intermediate phenonium ions, which react to aryl-migrated lactones.

Impregnated palladium on magnetite as a water compatible catalyst for the cycloisomerization of alkynoic acid derivatives

This work describes the catalytic activity of palladium(ii) species in the cycloisomerization of alkynoic acids and their derivatives in aqueous media as well as in Deep Eutectic Solvents (DESs), with one of the lowest metal catalyst loadings reported so far in the literature. Different substrates such as terminal and internal alkynes or alkynyl sulfonylimides were studied, obtaining selectivity either to the cyclic compound or the hydrolysed keto derivative. This new system avoids the use of harmful solvents and employs very efficient and recoverable heterogeneous catalysts.

Aerobic cascade oxidation of substituted cyclopentane-1,2-diones using metalloporphyrin catalysts

A method for the aerobic cascade oxidation of cyclopentane-1,2-diones using metal porphyrins as catalysts, yielding hydroxydiacids 2, ketoacid 3 and diketoacids 4 which are the intermediates of important biologically active compounds is reported. This method is operationally simple and can be employed under ambient conditions.

Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents

A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.

Intramolecular fluorocyclizations of unsaturated carboxylic acids with a stable hypervalent fluoroiodane reagent

A new class of fluorinated lactones was prepared by the intramolecular fluorocyclizations of unsaturated carboxylic acids by using the stable fluoroiodane reagent in combination with AgBF4. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step. The fluoroiodane reagent, prepared easily from fluoride, can also be used without a metal catalyst to give moderate yields within just 1 hour, thus demonstrating that it is a suitable reagent for developing new 18F-labelled radiotracers for PET imaging. All in one: A new class of lactones containing a tertiary alkyl fluoride was prepared in high yields by using a stable fluoroiodane reagent. This unique reaction incorporates a cyclization, an aryl migration, and a fluorination all in one step.

Lipase-catalyzed kinetic resolution of 2-phenylethanol derivatives and chiral oxa-Pictet-Spengler reaction as the key steps in the synthesis of enantiomerically pure tricyclic amines

A series of 5,6,7,8,9,10-hexahydro-5,9-epoxybenzocycloocten-6-amines have been synthesized and pharmacologically evaluated in receptor binding studies (σ1, σ2, NMDA, κ, and μ receptors). The first key step of the synthesis was a chir

Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones

3-Alkyl-1,2-cyclopentanediones 1 are transformed into 2-alkyl-2-hydroxyglutaric acid γ-lactones 3 in up to 83% isolated yields and up to 96% ee, affording a simple access to many bioactive compounds, including diacylglycerol lactones (DAG-lactones).

Regio- and Stereoselective Ring Opening of ω-Alkenyllactones Using Organocopper Reagents

New synthetic methods are described for the preparation of (E)-3, (E)-4, and (E)-5-alkenoic acids by the regio- and stereoselective ring opening of β, γ, and δ-lactones with unsaturated substituents at the ω-position using organocopper reagents such as halomagnesium diorganocuprates or Grignard reagents in the presence of copper(I) iodide.Both the organocopper reagents with primary, secondary, tertiary alkyl, and phenyl groups gave the corresponding carbon homologated alkenoic acids in good yields.Alkadienoic acids were also obtained in good yields by the reactions of ω-alkenyllactones with divinyl- and diallylcuprates.Utilizing the ring opening of β-isopropenyl-β-propiolactone, homoterpenoid carboxylic acids were easly obtained in good yields.The ring opening of β-(1-chlorovinyl)-β-propiolactone afforded 4-chloro-3-alkenoic acids which were easly transformed to 4-oxoalkanoic acids and 4-oxo-2-alkenoic acids.

A Synthesis of 4-Oxo Carboxylic Acids, 4-Oxo Aldehydes, and 1,4-Diketones from γ-Lactones

The α-methyldiphenylsilyl derivatives of γ-butyrolactone, γ-valerolactone, and the cis lactone of 2-hydroxycyclohexaneacetic acid have been reacted with Grignard reagents.The α-silylated lactones of γ-butyrolactone and γ-valerolactone react with a single equivalent of Grignard reagent to give a 2-substituted 4,5-dihydrofuran, which can be hydrolyzed and oxidized to 4-oxo carboxylic acids, 1,4-diketones, or 4-oxo aldehydes.The α-silylated fused lactone failed to react with ethylmagnesium bromide in refluxing tetrahydrofuran.An X-ray crystal structure of this silylated lactone indicated that this lack of reactivity is due to steric factors.