21622-00-4

Basic information

• Product Name: Diethyl 3-Cyclopentene-1,1-dicarboxylate
• Synonyms: Diethyl 3-Cyclopentene-1,1-dicarboxylate
• CAS NO: 21622-00-4
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.24234
• Mol File: 21622-00-4.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Diethyl 3-Cyclopentene-1,1-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 3-Cyclopentene-1,1-dicarboxylate(21622-00-4)
• EPA Substance Registry System: Diethyl 3-Cyclopentene-1,1-dicarboxylate(21622-00-4)

Safety Data

• Hazardous Substances Data: 21622-00-4(Hazardous Substances Data)

Usage

General Description

Diethyl 3-Cyclopentene-1,1-dicarboxylate is a chemical compound that is classified as an ester. It has the molecular formula C11H16O4 and a molecular weight of 216.24 g/mol. Diethyl 3-Cyclopentene-1,1-dicarboxylate is commonly used in the synthesis of pharmaceuticals, fragrances, and other organic compounds. It is a clear, colorless liquid with a fruity odor and is soluble in most organic solvents. Diethyl 3-Cyclopentene-1,1-dicarboxylate is known for its potential as a drug intermediate and its use in the creation of functionalized cyclopentane derivatives. However, it is important to handle this compound with care as it can be harmful if ingested, causes skin and eye irritation, and may have harmful effects on aquatic organisms.

Upstream product

• 1476-11-5 Z-1,4-dichlorobutene 
• 105-53-3 diethyl malonate 
• 3195-24-2 diallylmalonic acid diethyl ester 
• 899799-36-1 2-allyl-2-(2-benzenesulfonyl-5-phenyl-penta-2,3-dienyl)-malonic acid dimethyl ester 
• 1228236-01-8 C₁₃H₁₈⁽²⁾H₂O₄ 
• 4372-31-0 2,2-diallylmalonic acid 
• 3070-53-9 1,6-heptadiene 
• 1354716-14-5 diethyl 2-allyl-2-((4R,5R,E)-6-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-hydroxy-5-methyl-6-oxohex-2-enyl)malonate 
• 51481-46-0 2-allyl-2-but-3-enyl-malonic acid diethyl ester 
• 98-86-2 acetophenone 
• 931-88-4 cis-Cyclooctene 

Downstream Products

• 21622-01-5 ethyl 3-cyclopentene-1-carboxylate 
• 4167-77-5 cyclopentane-1,1-dicarboxylic acid diethyl ester 
• 76910-09-3 ethyl 1-(chloroformyl)cyclopent-3-ene-1-carboxylate 
• 199532-88-2 ethyl 1-aminocyclopent-3-ene-1-carboxylate 
• 541506-71-2 cyclopent-2-ene-1,1-dicarboxylic acid diethyl ester 
• 74-85-1 ethene 
• 3619-02-1 (S)-N-acetylalanine methyl ester 
• 19914-36-4 Methyl (R)-N-acetylalaninate 
• 1335226-59-9 C₁₀H₁₄O₄ 
• 76910-08-2 cyclopent-3-ene-1,1-dicarboxylic acid ethyl ester 
• 1295634-00-2 C₁₈H₂₆O₅S 
• 1295633-91-8 C₁₆H₂₂O₅S 
• 21736-07-2 diethyl 3-hydroxycyclopentane-1,1-dicarboxylate 
• 14377-05-0 1,1-cyclopent-3-enedimethanol bis(4-methylbenzenesulfonate) 

Relevant articles and documents

Solvents for ring-closing metathesis reactions

A study of the influence of eight diverse solvents on a Grubbs II-catalysed ring-closing metathesis (RCM) reaction reveals a complex dependence of the different reaction steps on the solvent and suggests acetic acid as a useful solvent for RCM reactions. The Royal Society of Chemistry.

Electrostatic immobilization of an olefin metathesis pre-catalyst on iron oxide magnetic particles

A quaternary ammonium Hoveyda-Grubbs olefin metathesis pre-catalyst has been reversibly immobilized on sulphonic acid-functionalised silica-coated iron oxide magnetic particles to affect ring closing metathesis with easy removal, reuse and regeneration.

Unprecedented Selectivity of Ruthenium Iodide Benzylidenes in Olefin Metathesis Reactions

The development of selective olefin metathesis catalysts is crucial to achieving new synthetic pathways. Herein, we show that cis-diiodo/sulfur-chelated ruthenium benzylidenes do not react with strained cycloalkenes and internal olefins, but can effectively catalyze metathesis reactions of terminal dienes. Surprisingly, internal olefins may partake in olefin metathesis reactions once the ruthenium methylidene intermediate has been generated. This unexpected behavior allows the facile formation of strained cis-cyclooctene by the RCM reaction of 1,9-undecadiene. Moreover, cis-1,4-polybutadiene may be transformed into small cyclic molecules, including its smallest precursor, 1,5-cyclooctadiene, by the use of this novel sequence. Norbornenes, including the reactive dicyclopentadiene (DCPD), remain unscathed even in the presence of terminal olefin substrates as they are too bulky to approach the diiodo ruthenium methylidene. The experimental results are accompanied by thorough DFT calculations.

Correction: Exploiting and understanding the selectivity of Ru-N-heterocyclic carbene metathesis catalysts for the ethenolysis of cyclic olefins to α,ω-Dienes (Journal of the American Chemical Society (2017) 139:37 (13117-13125) DOI: 10.1021/jacs.7b06947)

The isotropic chemical shielding (iso) was mislabeled as the isotropic chemical shift (iso) in Table S40, Figures 2, 4, S153 and in the respective discussion of these figures in the text. The corrected figures are shown below; the SI graphics are provided in the corrected SI file. In the conclusion section, "cyclic olefins" was incorrectly written as "cyclic dienes" to be the essential structural feature for the selective ethenolysis toward w-dienes. The ROMP activity of Ru-20 is not detectable in the "presence of ethylene"; this was incorrectly written as the "absence of ethylene". Equations 5 and 7, pages S47 and S135 respectively, had errors that have been fixed in the corrected SI file. None of the above affects any conclusions of the article. (Figure Presented).