4594-77-8

Basic information

• Product Name: 3-(2-OXOCYCLOPENTYL)PROPANENITRILE
• Synonyms: 3-(2-OXOCYCLOPENTYL)PROPANENITRILE;2-oxocyclopentanepropiononitrile;2-(2-CYANOETHYL)CYCLOPENTANONE;2-Oxocyclopentane-1-propiononitrile;2-Oxocyclopentanepropanenitrile;3-(2-Oxocyclopentyl)propiononitrile;3-(2-ketocyclopentyl)propionitrile
• CAS NO: 4594-77-8
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.17904
• EINECS: 224-990-0
• Mol File: 4594-77-8.mol

Chemical Properties

• Boiling Point: 285.2°Cat760mmHg
• Flash Point: 126.3°C
• Appearance: /
• Density: 1.033g/cm³
• Vapor Pressure: 0.00284mmHg at 25°C
• Refractive Index: 1.47
• CAS DataBase Reference: 3-(2-OXOCYCLOPENTYL)PROPANENITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-OXOCYCLOPENTYL)PROPANENITRILE(4594-77-8)
• EPA Substance Registry System: 3-(2-OXOCYCLOPENTYL)PROPANENITRILE(4594-77-8)

Safety Data

• Hazardous Substances Data: 4594-77-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11NO/c9-6-2-4-7-3-1-5-8(7)10/h7H,1-5H2

Upstream product

• 123-91-1 1,4-dioxane 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 107-13-1 acrylonitrile 
• 1614-92-2 1-(N-piperidino)cyclopentene 
• 120-92-3 cyclopentanone 

Downstream Products

• 82929-67-7 3-{2-[(Z)-1-Phenyl-ethylimino]-cyclopentyl}-propionitrile 
• 35579-33-0 3-(2,2-etylenedioxycyclopentyl)propionitrile 
• 88499-85-8 1,5,6,7-tetrahydro-2H-cyclopentan[b]pyridin-2-one 
• 117890-55-8 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine 
• 247185-52-0 (R)-7-hydroxy-2-phenyl-6,7-dihydro-5H-<1>pyridine 
• 114942-76-6 1-(2-Benzo[1,3]dioxol-5-yl-ethyl)-7-phenylselanyl-1-aza-spiro[4.4]nonane-2,6-dione 
• 114942-83-5 2-methoxy-3,8-dioxocephalotax-1-ene 
• 38848-21-4 (±)-cephalotaxine 
• 10333-13-8 1Δ^4a(7a)-hexahydro-2(1H)-pyrindone 

Relevant articles and documents

Method for preparing chiral nitrogen-phosphorus ligand L-8 containing pyridocyclopentane

The invention discloses a method for preparing chiral nitrogen-phosphorus ligand L-8 containing pyridocyclopentane, and belongs to the technical field of medical intermediate chiral ligands. The chiral nitrogen-phosphorus L-8 ligand is prepared from cyclopentanone through the steps of addition, cyclization, chlorination, asymmetric boronation, oxidation, coupling, esterification and the like in sequence, large-scale preparation is relatively easy to achieve through the route, and the defect that in a traditional route, the yield is low in the first step of ring closing reaction and chiral alcohol preparation is overcome, and by selecting a proper chiral ligand, and combining with butyl lithium, asymmetric synthesis of chiral alcohol is realized, and a chiral separation column mode adoptedin literature is avoided.

Method for synthesizing chiral nitrogen-phosphorus ligand L-8 containing pyridocycloheptane

The invention discloses a method for synthesizing a chiral nitrogen-phosphorus ligand L-8 containing pyridocycloheptane, and belongs to the technical field of medical intermediate chiral ligands. Thechiral nitrogen-phosphorus L-8 ligand is prepared from cyclopentanone through the steps of addition, cyclization, chlorination, asymmetric boronation, oxidation, coupling, esterification and the likein sequence, large-scale preparation is relatively easy to achieve through the route, and the defect that in a traditional route, the yield is low in the first step of ring closing reaction and chiralalcohol preparation, and by selecting a proper chiral ligand, and combining with butyl lithium, asymmetric synthesis of chiral alcohol is realized, and a chiral separation column mode adopted in literature is avoided.

Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles

The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf)3 and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.

Ligand-Enabled β-C–H Arylation of α-Amino Acids Without Installing Exogenous Directing Groups

Herein we report acid-directed β-C(sp3)-H arylation of α-amino acids enabled by pyridine-type ligands. This reaction does not require the installation of an exogenous directing group, is scalable, and enables the preparation of Fmoc-protected unnatural amino acids in three steps. The pyridine-type ligands are crucial for the development of this new C(sp3)-H arylation.

Regio- and stereoselective synthesis of chiral nitrilolactones using Baeyer–Villiger monooxygenases

This work describes the regio- and enantioselective synthesis of nitrile-containing chiral lactones from easily accessible ketone precursors using Baeyer–Villiger monooxygenases. These biocatalysts controlled the distribution of regioisomers much more tightly than commonly used stoichiometric reagents, additionally with good to excellent optical purity of products. A surprising case of strong stereoelectronic control was also observed. We tested a library of 14 catalysts using five-to eight-membered cyclic ketones with two different tether lengths to the nitrile group. In all but the largest series we found suitable wild-type enzymes for preparative scale synthesis of the target compounds. The diverse possibilities to further functionalize lactones and nitriles make this method interesting for the generation of chiral building blocks.

Design and synthesis of orally-active and selective azaindane 5HT2c agonist for the treatment of obesity

Based on our original pyrazine hit, CP-0809101, novel conformationally-restricted 5HT2c receptor agonists with 2-piperazin-azaindane scaffold were designed. Synthesis and structure-activity relationship (SAR) studies are described with emphasis on optimization of the selectivity against 5HT2a and 5HT2b receptors with excellent 2c potency. Orally-active and selective compounds were identified with dose-responsive in vivo efficacy in our pre-clinical food intake model.

STEREOSELECTIVE SYNTHESIS OF THE TRICYCLIC CONDENSED DERIVATIVES OF THIAZOLIDINE

The perhydro derivatives of thiazoloquinoline, thiazolocyclopentapyridine, thiazoloindole, and cyclopentapyrrolothiazole and also their 2-methyl derivatives were synthesized by the addition of thiirane and methylthiirane at the C=N bond in bicyclic imines of the 2,3,4,4a,5,6,7,8-octahydroquinoline type.An alternative method involves reaction of the thiiranes with amino ketones of the 2,2-ethylenedioxycyclohexylpropylamine type, protected at the carbomyl group, followed by acid deblocking and cyclization by treatment with alkali.The last method is the only method for the production of perhydrocyclopentapyrrolothiazoles, since 2,3,3a,4,5,6-hexahydrocyclopentapyrrole is not a stable imine.Some of the compounds were obtained in the form of single diastereomers, the configurations of which for the two subjects were determined by NMR.In other cases mixtures of the stereoisomers are formed with a srtong preponderance of one of them; arguments concerning their configurations are presented.It is shown that both methods of synthesis lead to an identical stereochemical result.

Synthesis of Ketones by Cyclization of Cyano and Acetylenic Radicals: Use of δ-Hydroxy Nitriles and δ- or ε-Hydroxy Acetylenes

The radical intermediates generated by deoxygenation of alcohols undergo intramolecular ring closure when suitably located triple bonds (CC or CN) are present; the reaction provides a new synthesis of bicyclic ketones from either monocyclic ketones or cyclic olefins.