25684-06-4

Usage

Synthesis Reference(s)

Synthesis, p. 104, 1975 DOI: 10.1055/s-1975-23673

InChI:InChI=1/C12H12O2/c13-11-7-6-10(12(11)14)8-9-4-2-1-3-5-9/h1-5,14H,6-8H2

Upstream product

• 1024613-07-7 1-benzyl-4-benzyloxy-5-oxo-cyclopent-3-ene-1,3-dicarboxylic acid diethyl ester 
• 55969-86-3 (cyclopent-2-en-1-ylmethyl)benzene 
• 930-30-3 cyclopent-2-enone 
• 3212-60-0 cyclopent-2-enol 
• 20657-21-0 3-acetoxycyclopent-1-ene 
• 62952-60-7 C₉H₈O₆^(2-)*2Na⁽¹⁺⁾ 
• 100-39-0 benzyl bromide 
• 6838-66-0 1,2-bis((trimethylsilyl)oxy)cyclopent-1-ene 

Downstream Products

• 3183-15-1 4-oxo-5-phenylvaleric acid 
• 1330064-97-5 C₁₂H₁₄O₃⁽¹⁸⁾O₂ 
• 1330064-96-4 C₁₂H₁₄O₃⁽¹⁸⁾O₂ 
• 1330065-03-6 C₁₂H₁₄O₄⁽¹⁸⁾O 
• 1330065-01-4 C₁₂H₁₂O₂⁽¹⁸⁾O₂ 
• 1330064-99-7 C₁₂H₁₂O₂⁽¹⁸⁾O₂ 
• 1340589-23-2 C₁₂H₁₂O₃⁽¹⁸⁾O 
• 1330064-93-1 [C₁-⁽¹⁸⁾O]-3-benzyl-2-hydroxy-cyclopent-2-en-1-one 

Relevant academic research and scientific papers

Structure Property Relationships of Carboxylic Acid Isosteres

The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The data set generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.

Heterogeneous platinum catalytic aerobic oxidation of cyclopentane-1,2- diols to cyclopentane-1,2-diones

A method for the aerobic oxidation of cyclopentane-1,2-diols to the corresponding diketones over a commercial heterogeneous Pt/C catalyst is described. Unsubstituted and 3- or 4-substituted cyclopentane-1,2-diols are oxidized to 1,2-dicarbonyl compounds in good yields under the reported optimized reaction conditions (atmospheric air, 1 mol % of catalyst, 1 equiv of LiOH, aqueous solvents and 60 °C temperature). The method is applicable for producing cyclopentane-1,2-diketones in a scalable manner.

Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3-benzyl-2-hydroxy-2-cyclopenten-1-one with an ee ≥96%, using the tartaric ester/Ti(OiPr)4/t-BuOOH complex, and transformed to the corresponding 4′-substituted nucleoside analogues with up to 61% overall yield.

Reactions of 1,2-bis(trimethylsilyloxy)cycloalkenes with the diethyl acetals of aldehydes

Lewis acid-mediated reactions of 1,2-bis(trimethylsilyloxy)-cyclobutene with acetals derived from a variety of aldehydes, followed by treatment with Amberlyst 15 resin in TFA, yielded 1,3-cyclopentanedione products, but reactions with 3,3-dimethyl-1,2-bis(trimethylsilyloxy)cyclobutene led to 1,2-cyclopentanediones. Reactions of 1,2-bis(trimethylsilyloxy)-cyclopentene gave intermediates that did not undergo skeletal rearrangement with Amberlyst 15 resin in TFA.

High yield "one-pot" synthesis of 2-hydroxy-3-methylcyclopent-2-en-1-one and related compounds

A convenient "one-pot" modification of a conventional synthetic route affords 2-hydroxy-3-methylcyclopent-2-en-1-one and related compounds in high overall yields.