49830-37-7

Usage

Uses

Used in Organic Synthesis:
1-Aminocyclopentane carbonitrile is used as a building block in organic synthesis for the creation of various biologically active molecules, leveraging its versatile chemical structure.
Used in Pharmaceutical Research:
In pharmaceutical research, 1-Aminocyclopentane carbonitrile is utilized as a building block for the synthesis of compounds with potential therapeutic applications, due to its ability to be incorporated into diverse molecular frameworks.
Used in Coordination Chemistry:
1-Aminocyclopentane carbonitrile is used as a ligand in coordination chemistry, contributing to the formation of metal complexes with specific properties and applications.
Used in Catalysis:
1-Aminocyclopentane carbonitrile also serves as a catalyst or a component in catalytic systems, facilitating chemical reactions in various industrial processes.
Used in Medicinal Chemistry for GABA Uptake Inhibition:
1-Aminocyclopentane carbonitrile is studied for its potential as a GABA uptake inhibitor, a property that may contribute to the development of treatments for neurological disorders.
Used in Medicinal Chemistry for Anticancer Properties:
Furthermore, it has been investigated for its anticancer properties, indicating its potential use in the development of novel cancer therapeutics.

InChI:InChI=1/C6H10N2/c7-5-6(8)3-1-2-4-6/h1-4,8H2

Upstream product

• 120-92-3 cyclopentanone 
• 773837-37-9 sodium cyanide 
• 5117-85-1 1-hydroxycyclopentanecarbonitrile 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 1003-03-8 Cyclopentamine 
• 7664-41-7 ammonia 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 151-50-8 potassium cyanide 
• 143-33-9 sodium cyanide 
• 67-64-1 acetone 

Downstream Products

• 52-52-8 1-amino-1-cyclopentanecarboxylic acid 
• 91806-24-5 1-Benzoylamino-cyclopentylnitril 
• 83521-99-7 cyclopentanespiro-4'-imidazolidine-2',5'-dithione 
• 17193-28-1 1-aminocyclopentane-1-carboxamide 
• 915086-69-0 4-(4-imino-2-thioxo-1,3-diazaspiro[4.4]non-3-yl)-2-trifluoromethylbenzonitrile 
• 194984-24-2 1-cyano-1-n-pentanoylaminocyclopentane 
• 877273-12-6 N-(1-cyanocyclopentyl)-13-cyclohexyl-7H-indolo[2,1-a][2]benzazepine-10-carboxamide 
• 6636-92-6 1-anilinocyclopentanecarbonitrile 
• 699-51-4 1,3-diazaspiro[4.4]nonane-2,4-dione 
• 74002-22-5 cyclopentanimine 
• 10316-79-7 (1-aminocyclopentyl)methanol 
• 1265634-43-2 5-(4-chlorophenyl)-N-(1-cyanocyclopentyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 92398-48-6 1-aminocyclopentanecarboxylic acid hydrochloride 

Relevant academic research and scientific papers

Total syntheses of (±)-massadine and massadine chloride

The total syntheses of the complex pyrrole-imidazole alkaloids (±)-massadine and (±)-massadine chloride is described using a carefully orchestrated sequence of manipulations on highly polar and structurally complex intermediates. Key to the completion of this synthetic endeavor was the exploration of a unique and chemoselective method to oxidize unprotected guanidines under aqueous conditions in air. This oxidation has been optimized and applied to a selection of spirocyclic guanidines of varying complexity. Additionally, the 3,7-epi analogues of these interesting natural products have been synthesized and fully characterized. Copyright

Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia

α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.

Synthesis of: N -unsubstituted cycloalkylimines containing a 4 to 8-membered ring

Primary cycloalkylimines with a 4 to 8-membered ring were synthesized by dehydrocyanation of the corresponding α-aminonitriles on solid potassium hydroxide via a vacuum gas-solid reaction. Imine-enamine tautomerism has been demonstrated at room temperature for the most kinetically stable derivatives.

Photoreactive fused aziridinylpiperazines on the background of 4-substituted chalcones and their benzimidazolic analogs

The reaction of bromo-substituted chalcones with various diamino-compounds leads to the fused heterocyclic products, aziridinylpiperazines, exhibiting photoreactivity in the crystalline state. Crystals of 4-nitrosubstituted compounds of this family change their color from yellowish to deep violet-blue, 4-cyanosubstituted ones – from yellowish to pink at UV irradiation. Discussion on the mechanism of this phototransformation is still in progress, however, several facts points to the free radial nature of the photogenerated colored semi-products stabilized only by crystalline state of the irradiated samples. Formation of a mixture of positional isomers at interaction of bromo-chalcones with asymmetric diamines of aliphatic/alicyclic or aromatic series at synthesis of the title compounds is of significant interest as well.

A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins

Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas–liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52–84 %).

Design and Synthesis of Fsp3-Rich, Bis-Spirocyclic-Based Compound Libraries for Biological Screening

The exploration of innovative chemical space is a critical step in the early phases of drug discovery. Bis-spirocyclic frameworks occur in natural products and other biologically relevant metabolites and show attractive features, such as molecular compactness, structural complexity, and three-dimensional character. A concise approach to the synthesis of bis-spirocyclic-based compound libraries starting from readily available commercial reagents and robust chemical transformations has been developed. A number of novel bis-spirocyclic scaffold examples, as implemented in the European Lead Factory project, is presented.

Continuous-flow oxidative cyanation of primary and secondary amines using singlet oxygen

Primary and secondary amines can be rapidly and quantitatively oxidized to the corresponding imines by singlet oxygen. This reactive form of oxygen was produced using a variable-temperature continuous-flow LED-photoreactor with a catalytic amount of tetraphenylporphyrin as the sensitizer. α- Aminonitriles were obtained in good to excellent yields when trimethylsilyl cyanide served as an insitu imine trap. At 25°C, primary amines were found to undergo oxidative coupling prior to cyanide addition and yielded secondary α-aminonitriles. Primary α-aminonitriles were synthesized from the corresponding primary amines for the first time, by an oxidative Strecker reaction at -50 °C. This atom-economic and protecting-group-free pathway provides a route to racemic amino acids, which was exemplified by the synthesis of tert-leucine hydrochloride from neopentylamine. The mild synthesis of imines paves the way to aminonitriles and amino acids. Aerobic oxidation of primary and secondary amines in a continuous photoreactor with singlet oxygen generated insitu led to the rapid formation of imines, which were quantitatively trapped as α-aminonitriles (see scheme; TMS=trimethylsilyl). Benzylic and primary α-aminonitriles, precursors for amino acids, could be efficiently produced in three minutes.

Transamination of a-amino nitriles

α-Amino nitriles containing a primary amino group undergo transamination with aliphatic and aromatic amines under mild conditions with high yields. A probable reaction mechanism involving intermediate elimination of cyanide ion has been proposed.

Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC)

A structure-activity relationship study was carried out on a series of thiohydantoins and their analogues 14 which led to the discovery of 92 (MDV3100) as the clinical candidate for the treatment of hormone refractory prostate cancer.

AN IMPROVED PROCESS FOR PREPARING 1-(PENTANOYLAMINO)CYCLOPENTANECARBOXYLIC ACID

The present invention relates to an improved process for preparing 1-(pentanoylamino)cyclopentanecarboxylic acid formula (I) which is useful intermediate for the preparation of Irbesartan.