21622-00-4

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl 3-Cyclopentene-1,1-dicarboxylate is used as a drug intermediate for its potential in the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of functionalized cyclopentane derivatives, which are valuable in the development of new medications.
Used in Fragrance Industry:
In the fragrance industry, Diethyl 3-Cyclopentene-1,1-dicarboxylate is used as a key component in the formulation of various scents. Its fruity odor makes it a desirable ingredient for creating pleasant and appealing fragrances.
Used in Organic Compounds Synthesis:
Diethyl 3-Cyclopentene-1,1-dicarboxylate is used as a reagent in the synthesis of other organic compounds. Its versatility in chemical reactions makes it a valuable asset in the creation of a wide range of organic molecules.
However, it is crucial to handle Diethyl 3-Cyclopentene-1,1-dicarboxylate with care, as it can be harmful if ingested, causes skin and eye irritation, and may have harmful effects on aquatic organisms. Proper safety measures should be taken during its use to minimize potential risks.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Well-defined ruthenium olefin metathesis catalysts: Mechanism and activity

Several ruthenium-based olefin metathesis catalysts of the formula (PR3)2X2Ru=CHCHCPh2 have been synthesized, and relative catalyst activities were determined by monitoring the ring-closing metathesis of the acyclic diene diethyl diallylmalonate. The following order of increasing activity was determined: X = I 3 = PPh3 2Ph 2Ph 3 3. Additional studies were conducted with the catalyst (PCy3)2-Cl2Ru=CH2 to probe the mechanism of olefin metathesis by this class of catalysts. The data support a scheme in which there are two competing pathways: the dominant one in which a phosphine dissociates from the ruthenium center and a minor one in which both phosphines remain bound. Higher catalyst activities could be achieved by the addition of CuCl to the reaction.

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.

Synthesis of Vanadium Oxo Alkylidene Complex and Its Reactivity in Ring-Closing Olefin Metathesis Reactions

V imido alkylidenes have been applied for the ring-opening metathesis polymerization involving cyclic olefins. However, those complexes found limited application in reactions with acyclic terminal olefins due to instability toward ethylene. Experimental and theoretical studies show that the β-hydride elimination from unsubstituted metallacyclobutene is the primary decomposition pathway in those systems. Herein, we report the synthesis of the first catalytically active V oxo alkylidene, VO(CHSiMe3)(PEt3)2Cl, which exhibits the highest reported productivity with various terminal olefins in ring-closing metathesis reactions among known V catalysts. Presented DFT studies indicate that β-hydride elimination is significantly disfavored for V oxo species.

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.

Direct observation of Ru-alkylidene forming into ethylene in ring-closing metathesis from hyperpolarized 1H NMR

Ring-closing metathesis was monitored using real-time NMR of 1H hyperpolarized olefins at room temperature. By applying a selective saturation to an observable intermediate, its protons were found to transfer to ethylene. The intermediate was thus identified as a Ru-alkylidene species, which appears in the ethylene formation pathway.

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).

Condensation of СН-acids with cis-1,4-dichlorobut-2-ene

Synthesis of tri- and five-membered carboxylates are discussed. Microwave irradiation has been shown to stimulate the condensation of СН-acids with allyl chlorides. The selectivity of formation of target products was depending on the CH-acid structure. St

Exploiting and understanding the selectivity of Ru-N-Heterocyclic carbene metathesis catalysts for the ethenolysis of cyclic olefins to α,ω-Dienes

A library of 29 homologous Ru-based olefin metathesis catalysts has been tested for ethenolysis of cyclic olefins toward the goal of selectively forming α,ω-diene using cis-cyclooctene as a prototypical substrate. Dissymmetry at the N-heterocyclic carbene (NHC) ligand was identified as a key parameter for controlling the selectivity. The best-performing catalyst bearing an N-CF3 group significantly outperformed the benchmark second-generation Grubbs catalyst in the ethenolysis of cis-cyclooctene. Application of this optimal catalyst to the ethenolysis of various norbornenes allows the efficient synthesis of valuable diene intermediates in good yields. The observed ligand effect trends could be rationalized through univariate and multivariate parameter analysis involving steric and electronic descriptors of the NHC ligand in the form of the buried volume and the 77Se NMR chemical shift, in particular the σyy component of the shielding tensor of [Se(NHC)] model compounds, respectively. Natural chemical shift analysis of this chemical shielding tensor shows that σyy probes the I-Acceptor property of the NHC ligand, the essential electronic parameter that drives the relative rate of degenerate metathesis and selectivity in ethenolysis with catalysts bearing dissymmetric NHC ligands.

Asymmetric Transfer Hydrogenation of Ketones with Modified Grubbs Metathesis Catalysts: On the Way to a Tandem Process

Herein, we report the successful transformation of a 1st generation Grubbs metathesis catalyst into an asymmetric transfer hydrogenation (ATH) catalyst. Upon addition of a chiral amine ligand, an alcohol and a base, the 1st generation Hoveyda-Grubbs catalyst (HG-I) was found to promote the enantioselective reduction of acetophenone to 1-phenylethanol. After optimizing the order of addition and the reaction conditions, the substrate scope was assessed leading to enantiomeric excesses up to 97% ee. NMR experiments were run in order to get information about the in situ-generated ATH catalyst. Furthermore, the possibility to perform olefin metathesis and ketone transfer hydrogenation sequentially in one pot was demonstrated, and the first tandem olefin metathesis-ketone asymmetric transfer hydrogenation was carried out.