4167-77-5

Usage

Uses

Used in Pharmaceutical Synthesis:
Diethyl 1,1-cyclopentanedicarboxylate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to facilitate the creation of complex organic molecules. Its chemical reactivity and ester functionality contribute to the development of new drugs and medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, diethyl 1,1-cyclopentanedicarboxylate is utilized as a precursor in the synthesis of pesticides and other crop protection agents. Its role in these applications is to provide a stable and effective platform for the development of compounds that protect crops from pests and diseases.
Used in Organic Compound Synthesis:
Diethyl 1,1-cyclopentanedicarboxylate is employed as a versatile building block in the synthesis of a broad spectrum of organic compounds. Its ester group and cycloalkane ring structure make it a suitable candidate for various organic reactions, leading to the formation of diverse chemical entities.
Used as a Fragrance or Flavoring Agent:
Diethyl 1,1-cyclopentanedicarboxylate may be used as a fragrance or flavoring agent in certain consumer products. Its unique chemical properties allow it to impart specific scents or tastes, enhancing the sensory experience of the products in which it is incorporated.
Overall, diethyl 1,1-cyclopentanedicarboxylate is a multifaceted chemical compound with applications spanning across various industries, highlighting its importance in modern chemical synthesis and product development.

InChI:InChI=1/C11H18O4/c1-3-14-9(12)11(7-5-6-8-11)10(13)15-4-2/h3-8H2,1-2H3

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 64-17-5 ethanol 
• 996-82-7 sodium diethylmalonate 
• 5802-65-3 cyclopentane-1,1-dicarboxylic acid 
• 110-56-5 1,4-dichlorobutane 
• 105-53-3 diethyl malonate 
• 18719-44-3 diethyl 2-(4-chlorobutyl)malonate 
• 28247-05-4 2-(4-Methylsulfanyl-butyl)-malonic acid diethyl ester 
• 74-88-4 methyl iodide 
• 132525-49-6 diethyl 2-(4-bromobutyl)propanedioate 
• 137435-36-0 2-{2-[(Z)-2-Phenyl-aziridin-1-ylimino]-ethyl}-2-(2-phenylselanyl-ethyl)-malonic acid diethyl ester 
• 2121-66-6 tetraethyl 1,1,3,3-propanetetracarboxylate 
• 141-52-6 sodium ethanolate 
• 137435-55-3 diethyl (2-bromoethyl)(2-oxoethyl)propanedioate 

Downstream Products

• 56209-30-4 7,9-diaza-spiro[4.5]decane-6,8,10-trione 
• 5763-53-1 1,1-bis-(hydroxymethyl)cyclopentane 
• 5453-85-0 ethyl cyclopentanecarboxylate 
• 77500-72-2 4-(1,4-Dioxo-2,3-diaza-spiro[4.4]non-2-yl)-2-hydroxy-benzoic acid ethyl ester 
• 77500-90-4 7-(4-Ethoxy-phenyl)-7,9-diaza-spiro[4.5]decane-6,8,10-trione 
• 77509-26-3 7-m-Tolyl-7,9-diaza-spiro[4.5]decane-6,8,10-trione 
• 16418-55-6 2-phenyl-2,3-diazaspiro[4.4]nonane-1,4-dione 
• 77500-80-2 2-Benzenesulfonyl-3-phenyl-2,3-diaza-spiro[4.4]nonane-1,4-dione 
• 10316-79-7 (1-aminocyclopentyl)methanol 
• 1664-35-3 ethyl 1-aminocyclopentanecarboxylate 
• 76910-12-8 1-Chlorformyl-1-cyclopentancarbonsaeure-ethylester 
• 76910-15-1 1,1'-<(5-Nitro-4,6-pyrimidindiyl)diamino>-1,1'-dicyclopentanmethanol 
• 60395-51-9 Spiro 

Relevant academic research and scientific papers

Helianthus-like cucurbit[4]uril and cucurbit[5]uril analogues

A new glycoluril-like molecule, cyclopentanopropanediurea (CyP-TD), was prepared by malonic ester synthesis. Its condensation with paraformaldehyde resulted in two Helianthus-like cucurbituril analogues, CyP4TD[4] and CyP5TD[5], with cyclopentano groups evenly distributed on the equators. The structures of the two macrocycles were confirmed by 1H-NMR, HRMS-ES and single-crystal X-ray diffraction. CyP4TD[4] and CyP5TD[5] both exhibit excellent thermal stability, and CyP5TD[5] has better solubility in water and organic solvents, while CyP4TD[4] can hardly dissolve in them.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

Asymmetric Cyclization/Nucleophilic Tandem Reaction of o-Alkynylacetophenone with (Diazomethyl)phosphonate for the Synthesis of Functional Isochromenes

An efficient asymmetric reaction between (diazomethyl)phosphonate with o-alkynylacetophenone has been established by employing different stereocontrol strategy. A variety of isochromenes bearing tetrasubstituted stereocenters and (diazomethyl)phosphonate at the 1-position were prepared in yield up to 99% with enantioselectivity up to 94% enantiomeric excess (ee) for the first time. These functional isochromenes could be transformed to important structural motifs in biologically active compounds. Moreover, density functional theory calculations were conducted to gain insight into the process and the stereoselectivity.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

A Selective and Functional Group-Tolerant Ruthenium-Catalyzed Olefin Metathesis/Transfer Hydrogenation Tandem Sequence Using Formic Acid as Hydrogen Source

A ruthenium-catalyzed transfer hydrogenation of olefins utilizing formic acid as a hydrogen donor is described. The application of commercially available alkylidene ruthenium complexes opens access to attractive C(sp3)-C(sp3) bond formation in an olefin metathesis/transfer hydrogenation sequence under tandem catalysis conditions. High chemoselectivity of the developed methodology provides a remarkable synthetic tool for the reduction of various functionalized alkenes under mild reaction conditions. The developed methodology is applied for the formal synthesis of the drugs pentoxyverine and bencyclane.

Discovery of Peptidomimetic Antibody-Drug Conjugate Linkers with Enhanced Protease Specificity

Antibody-drug conjugates (ADCs) have become an important therapeutic modality for oncology, with three approved by the FDA and over 60 others in clinical trials. Despite the progress, improvements in ADC therapeutic index are desired. Peptide-based ADC linkers that are cleaved by lysosomal proteases have shown sufficient stability in serum and effective payload-release in targeted cells. If the linker can be preferentially hydrolyzed by tumor-specific proteases, safety margin may improve. However, the use of peptide-based linkers limits our ability to modulate protease specificity. Here we report the structure-guided discovery of novel, nonpeptidic ADC linkers. We show that a cyclobutane-1,1-dicarboxamide-containing linker is hydrolyzed predominantly by cathepsin B while the valine-citrulline dipeptide linker is not. ADCs bearing the nonpeptidic linker are as efficacious and stable in vivo as those with the dipeptide linker. Our results strongly support the application of the peptidomimetic linker and present new opportunities for improving the selectivity of ADCs.

Metal- and additive-free oxygen-atom transfer reaction: an efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides

Metal- and additive-free oxidation of a series of sulfides/thioketones has been achieved using cyclic diacyl peroxides as mild oxygen sources. This protocol features simple manipulation, high chemo- and diastereoselectivity, and a broad substrate scope (up to 42 examples), tolerates many common functional groups, and is scalable and applicable to the late-stage sulfoxidation strategy. A preliminary mechanistic study by quantum mechanical calculations suggests that a single two-electron transfer process is energetically more favorable, and indicates the reactivity of cyclic diacyl peroxides distinct from conventional acyclic acyl peroxides.

In tandem or alone: A remarkably selective transfer hydrogenation of alkenes catalyzed by ruthenium olefin metathesis catalysts

A system for transfer hydrogenation of alkenes, composed of a ruthenium metathesis catalyst and HCOOH, is presented. This operationally simple system can be formed directly after a metathesis reaction to effect hydrogenation of the metathesis product in a single-pot. These hydrogenation conditions are applicable to a wide range of alkenes and offer remarkable selectivity. This journal is

PEPTIDOMIMETIC COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF

This invention relates to peptidomimetic linkers and anti-body drug conjugates thereof, to pharmaceutical compositions containing them, and to their use in therapy for the prevention or treatment of cancer.

Assisted Tandem Catalysis: Metathesis Followed by Asymmetric Hydrogenation from a Single Ruthenium Source

Here we report the first example of a tandem metathesis-asymmetric hydrogenation protocol where the prochiral olefin generated by metathesis is hydrogenated with high enantioselectivity by an in situ formed chiral ruthenium catalyst. We show that either the ruthenium metathesis catalysts or the ruthenium species formed during the metathesis reaction can be converted into an efficient asymmetric hydrogenation catalyst upon addition of a chiral ligand and an alcohol. The performance in asymmetric hydrogenation appears to be very dependent on the solvent, the chiral ligand, and the prochiral substrate.