36601-73-7

Usage

Uses

1. Used in Chemical Synthesis:
1-Cyclopentene-1-carboxylic acid, 5-oxo-, methyl ester (9CI) is used as an intermediate in the synthesis of Aflatoxin B2-d3 (A357467), which is a labeled standard. 1-Cyclopentene-1-carboxylicacid,5-oxo-,methylester(9CI) plays a crucial role in the production of various chemical substances, contributing to the development of new materials and compounds with potential applications in different industries.
2. Used in Environmental and Food Contaminant Research:
As an intermediate in the synthesis of Aflatoxins B1, B2, G1, and G2, 1-Cyclopentene-1-carboxylic acid, 5-oxo-, methyl ester (9CI) is involved in the study and analysis of these secondary metabolites produced by fungal species such as Aspergillus flavus or Aspergillus parasiticus. These aflatoxins are very carcinogenic mycotoxins with hepatotoxic effects, and their presence in various foods like peanuts, nuts, spices, and cereals poses a significant health risk. 1-Cyclopentene-1-carboxylicacid,5-oxo-,methylester(9CI)'s role in the synthesis of these toxins aids in understanding their impact on the environment and food safety.
3. Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, the compound's involvement in the synthesis of aflatoxins, which are known carcinogens, suggests that it may also have potential applications in the pharmaceutical industry. It could be used in the development of drugs or therapies targeting cancer or other diseases related to the toxins produced by Aspergillus species.

Upstream product

• 105405-22-9 methyl 2-oxo-1-(phenylselanyl)cyclopentane-1-carboxylate 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 5707-04-0 Phenylselenyl chloride 
• 143921-19-1 Methyl 2-diazo-6-methoxy-3-oxohexanoate 
• 67-56-1 methanol 
• 10481-34-2 2-bromo-2-cyclopenten-1-one 
• 201230-82-2 carbon monoxide 
• 33948-35-5 2-iodo-cyclopent-2-enone 
• 143921-18-0 Methyl 6-methoxy-3-oxohexanoate 
• 120746-21-6 ((Ξ)-5-oxo-dihydro-[2]furyliden)-acetic acid methyl ester 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 686737-76-8 (1S,5R)-1-methoxycarbonyl-2-oxo-7-(phenylthio)-bicyclo[3.2.0]hept-6-ene 
• 686738-16-9 (1R,5S)-1-methoxycarbonyl-2-oxo-7-(phenylthio)-bicyclo[3.2.0]hept-6-ene 
• 2630-44-6 3-(hydroxycarbonylmethyl)cyclopentan-1-one 
• 2630-37-7 3-(hydroxycarbonylmethyl)cyclopentan-1-one 
• 1207173-82-7 3,4-dibenzyloxy-1-methoxycarbonyl-9-oxo-bicyclo[4.3.0]oct-3-ene 
• 1258209-17-4 methyl 2-oxo-5-(5-oxo-2,5-dihydrofuran-2-yl)cyclopentanecarboxylate 

Relevant academic research and scientific papers

Electronic effects in dirhodium(II) carboxylates. Linear free energy relationships in catalyzed decompositions of diazo compounds and CO and isonitrile complexation

A linear free energy analysis of substituent effects in rhodium carboxylate complexes has been conducted. Two reactions of diazo compounds involving intramolecular competition between (1) O-ylide formation and secondary C-H insertion, and (2) tertiary C-H and primary C-H insertion were studied as well as complexation effects on the IR frequencies of CO and tert-butyl isocyanide. Aliphatic and aromatic carboxylate complexes were included. Regression equations that describe these processes include contributions from σa(polarizability) and σF(field effects) and, for the benzoates, σR (resonance). Complexes that deviate from the LFER include rhodium trifluoroacetate and rhodium triptycenecarboxylate, and their behavior was explained through (partial) release of the free carbene. The effect of ligand polarizability on selectivity in these reactions was interpreted as evidence for the importance of backbonding from rhodium to the carbene carbon in the product-determining step. The ability of these complexes to backbond was shown through the complexation study. Higher selectivity with increasing ability to backbond is analogous to other carbenes such as difluorocarbene. Increased selectivity engendered by backbonding could occur by facilitating the reversal of an intermediate complex between the carbenoid and the C-H bond undergoing insertion. Increased selectivity engendered by field effects and polarizability could be explained by increased selectivity for electron-rich sites.

Highly Reactive and Tracelessly Cleavable Cysteine-Specific Modification of Proteins via 4-Substituted Cyclopentenone

A rapid and cysteine-specific modification of proteins using 4-substituted cyclopentenone via a Michael addition tandem elimination reaction was developed. Compared to the classical method, this reaction featured fast kinetics with a stable product. More importantly, this conjugation could be tracelessly removed by exchange with a Michael addition donor. The conjugation and regeneration process not only exhibited little change to the structures or conformations of the proteins but also exhibited little disturbance to their biological functions, such as their enzymatic activities.

Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: Towards the synthesis of magellanine-type: Lycopodium alkaloids

The pronounced beneficial effect of a precise amount of protic additive in an enantioselective Cu-catalysed Diels-Alder reaction is reported. This reaction, which employs a cyclic alkylidene β-ketoester as a dienophile, represents one of the first example

A unifying synthesis approach to the C18-, C19-, and C20-diterpenoid alkaloids

The secondary metabolites that comprise the diterpenoid alkaloids are categorized into C18, C19, and C20 families depending on the number of contiguous carbon atoms that constitute their central framework. Herein, we detail our efforts to prepare these molecules by chemical synthesis, including a photochemical approach, and ultimately a bioinspired strategy that has resulted in the development of a unifying synthesis of one C18 (weisaconitine D), one C19 (liljestrandinine), and three C20 (cochlearenine, paniculamine, and N-ethyl-1α-hydroxy-17-veratroyldictyzine) natural products from a common intermediate.

Synthetic efforts toward the Lycopodium alkaloids inspires a hydrogen iodide mediated method for the hydroamination and hydroetherification of olefins

Progress toward the total syntheses of a diverse set of fawcettimine-type Lycopodium alkaloids via a "Heathcock-type" 6-5-9 tricycle is disclosed. This route features an intermolecular Diels-Alder cycloaddition to rapidly furnish the 6-5-fused bicycle and a highly chemoselective directed hydrogenation to build the azonane fragment. While conducting these synthetic studies, trimethylsilyl iodide was found to effect a hydroamination reaction to furnish the tetracyclic core of serratine and related natural products. This observation has been expanded into a general method for the room temperature hydroamination of unactivated olefins with tosylamides utilizing catalytic "anhydrous" HI (generated in situ from trimethylsilyl iodide and water). The presence of the iodide anion is critical to the success of this Bronsted acid catalyzed protocol, possibly due to its function as a weakly coordinating anion. These conditions also effect the analogous hydroetherification reaction of alcohols with unactivated olefins.

Synthesis and Applications of Hajos-Parrish Ketone Isomers

Numerous natural products possess ring systems and functionality for which Hajos-Parrish ketone isomers with a transposed methyl group (termed "iso-Hajos-Parrish ketones") would be of value. However, such building blocks have not been exploited to the sam

Tandem Diels-Alder and retro-ene reactions of 1-sulfenyl- and 1-sulfonyl-1,3-dienes as a traceless route to cyclohexenes

A pericyclic approach for the synthesis of six-membered ring structures is described. The method employs 1,3-dienes with a 1-sulfur substituent in a tandem sequence of Diels-Alder and retro-ene reactions. In this pairing of [4 + 2] cycloaddition and 1,5-sigmatropic rearrangement, 1-sulfenyl-1,3-dienes engage in Diels-Alder reactions with electron-deficient dienophiles. Subsequently, the sulfenyl group of the cycloadducts is oxidized and unmasked to form allylic sulfinic acids, which undergo sterospecific reductive transposition via sulfur dioxide extrusion. The sequence can also include an inverse electron demand Diels-Alder reaction by using a 1-sulfonyl-1,3-diene. This combination of two pericyclic events offers novel stereocontrolled access to cyclohexenes that are inaccessible via a direct [4 + 2] cycloaddition route.

Palladium-catalyzed dehydrogenative β'-functionalization of β-keto esters with indoles at room temperature

The dehydrogenative β'-functionalization of α-substituted β-keto esters with indoles proceeds with high regioselectivities (C3-selective for the indole partner and β′-selective for the β-keto ester) and good yields under mild palladium catalysis at room temperature with a variety of oxidants. Two possible mechanisms involving either late or early involvement of indole are presented.

Synthesis of the bridging framework of phragmalin-type limonoids

An efficient synthesis of the octahydro-1H-2,4-methanoindene core of phragmalin-type limonoids, such as xyloccensins O and P, is reported. The success of the synthetic route is predicated on the use of network analysis in the retrosynthetic analysis and a

Palladium-catalyzed dehydrogenative β′-arylation of β-keto esters under aerobic conditions: Interplay of metal and Bronsted acids

The Bronsted aids: The first dehydrogenative arylation of β-keto esters with arenes under ambient aerobic conditions is described (see scheme). Under a PdII/Bronsted acid co-catalytic system, regioselective arylations with alkoxylated arenes an