18928-91-1

Basic information

• Product Name: Diethyl cyclopentylmalonate
• Synonyms: Diethylcyclopentylpropanedioate;DIETHYL CYCLOPENTYLMALONATE;CYCLOPENTYLMALONIC ACID DIETHYL ESTER;cyclopentylmalonicaciddiethylester95+%;2-Cyclopentylmalonic acid diethyl ester;Nsc67358;Cyclopentyl-Diethyl;diethyl 2-cyclopentylmalonate
• CAS NO: 18928-91-1
• Molecular Formula: C₁₂H₂₀O₄
• Molecular Weight: 228.28
• Mol File: 18928-91-1.mol

Chemical Properties

• Boiling Point: 138 °C / 13mmHg
• Flash Point: 127.6°C
• Appearance: /
• Density: 1,03 g/cm3
• Vapor Pressure: 0.00441mmHg at 25°C
• Refractive Index: 1.4430-1.4450
• CAS DataBase Reference: Diethyl cyclopentylmalonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl cyclopentylmalonate(18928-91-1)
• EPA Substance Registry System: Diethyl cyclopentylmalonate(18928-91-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 18928-91-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl cyclopentylmalonate is used as a reagent or intermediate for the synthesis of various pharmaceutical compounds. Its ester functional groups facilitate essential chemical reactions, making it a valuable component in the development of new medications.
Used in Organic Synthesis:
In the field of organic synthesis, Diethyl cyclopentylmalonate is employed as a versatile reagent or intermediate. Its ester functional groups enable it to participate in a wide range of chemical reactions, contributing to the synthesis of diverse organic compounds.
Handling and Storage:
Diethyl cyclopentylmalonate requires industry-standard procedures for handling and storage, similar to other organic compounds. Proper care should be taken to ensure the stability and safety of this chemical during its use in various applications.

InChI:InChI=1/C12H20O4/c1-3-15-11(13)10(12(14)16-4-2)9-7-5-6-8-9/h9-10H,3-8H2,1-2H3

Upstream product

• 1556-18-9 cyclopentyl iodide 
• 996-82-7 sodium diethylmalonate 
• 137-43-9 Cyclopentyl bromide 
• 105-53-3 diethyl malonate 
• 17247-58-4 (Bromomethyl)cyclobutane 
• 41589-42-8 2-cyclopentylidenemalonic acid diethyl ester 
• 120-92-3 cyclopentanone 
• 18322-54-8 ethyl cyclopentylacetate 
• 623-49-4 ethyl cyanoformate 
• 53608-93-8 diethyl 2-(cyclopenten-1-yl)propane-1,3-dioate 

Downstream Products

• 101112-75-8 5-cyclopentyl-1-phenyl-barbituric acid 
• 5660-81-1 2-cyclopentylpropanedioic acid 
• 5305-07-7 4-cyclopentyl-2-phenyl-isoxazolidine-3,5-dione 
• 66016-20-4 3-Cyclopentyl-cyclobutan-1-carbonsaeure 
• 16418-55-6 2-phenyl-2,3-diazaspiro[4.4]nonane-1,4-dione 
• 291773-88-1 2-benzyl-2,3-diazaspiro[4.4]nonane-1,4-dione 
• 291773-87-0 2-(p-tolyl)-2,3-diazaspiro[4.4]nonane-1,4-dione 
• 132101-48-5 Toluene-4-sulfonic acid (R)-2-cyclopentyl-1-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-allyl ester 
• 107056-78-0 5-cyclopentyl-5-hydroxy-1-phenyl-barbituric acid 
• 107516-32-5 N-(cyclopentyl-hydroxy-acetyl)-N'-phenyl-urea 
• 107518-12-7 N-(cyclopentyl-hydroxy-acetyl)-N-phenyl-urea 
• 109438-85-9 2-cyclopentyl-2-hydroxy-N-phenylcarbamoyl-malonamic acid 
• 7028-22-0 2-cyclopentylpropanoic acid 
• 5452-76-6 C₁₀H₁₈O₃ 

Relevant articles and documents

A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides

Enantioenriched tertiary alkyl halides are prevalent in bioactive molecules and can serve as versatile synthetic intermediates to construct complex structures. While conventional access to these motifs often hinges on stereoselective carbon-halogen or carbon-carbon bond formation reactions, desymmetric approaches using halogenated and prochiral tetrasubstituted carbons are largely elusive in comparison. Here, we report that a suite of dinuclear zinc catalysts with a prolinol- or pipecolinol-derived tetradentate ligand can reductively desymmetrize a large collection of easily available halomalonic esters to α-halo-β-hydroxyesters. These polyfunctionalized tertiary alkyl fluorides, chlorides, and bromides proved to be useful intermediates toward fluorinated drug analogs and polyhalogenated monoterpenes. The facile intramolecular epoxidation of the chiral chloride and bromide products has also enabled expeditious access to natural products containing tertiary alcohol motifs.

Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates

An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.

Chiral compound, liquid crystal composition containing the chiral compound, optically anisotropic body, and liquid crystal display device

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Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization

Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.

Computational and experimental studies on copper-mediated selective cascade C-H/N-H annulation of electron-deficient acrylamide with arynes

An efficient and convenient copper-mediated method has been developed to achieve direct cascade C-H/N-H annulation to synthesize 2-quinolinones from electron-deficient acrylamides and arynes. This method highlights an emerging but simple strategy to transform inert C-H bonds into versatile functional groups in organic synthesis to provide a new method of synthesizing 2-quinolinones efficiently. Mechanistic investigations by experimental and density functional theory (DFT) studies suggest that an organometallic C-H activation via a Cu(iii) intermediate is likely to be involved in the reaction.

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