22912-25-0

Usage

Type of compound

Pyrrolidine derivative

Functional groups

Cyano group and cyclohexyl ring

Usage

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Biological activity

Potential applications in medicinal chemistry research

Molecular weight

192.3 g/mol

Physical state

White to off-white solid

Versatility

Diverse uses and potential biological significance

InChI:InChI=1/C11H18N2/c12-10-11(6-2-1-3-7-11)13-8-4-5-9-13/h1-9H2

Upstream product

• 123-75-1 pyrrolidine 
• 151-50-8 potassium cyanide 
• 108-94-1 cyclohexanone 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 143-33-9 sodium cyanide 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 14228-29-6 1-pyrrolidin-1-yl-1-vinylcyclohexane 
• 41907-01-1 1-pyrrolidin-1-yl-cyclohexanecarboxylic acid amide 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 39627-14-0 (2-cyclohexylideneethyl)benzene 
• 2129-93-3 n-propylidenecyclohexane 
• 21623-78-9 1-methyl-1-vinylcyclohexane 

Relevant academic research and scientific papers

Syntheses of fluorinated phencyclidine analogs

Syntheses of several fluorinated phencyclidine (PCP) analogs are described. These compounds are being used to probe PCP binding sites on N-methyl-D-aspartate (NMDA) receptors. The compounds were prepared in good yields by Grignard reaction of appropriate fluorine substituted bromobenzene with carbonitrile intermediates. Syntheses of the known compound 1-[1-(3-fluorophenyl) cyclohexyl]piperidine, and the novel compounds 1-[1-(4-fluorophenyl)cyclohexyl]piperidine, 1-[1-(3-fluorophenyl) cyclohexyl]pyrrolidine, and 1-[1-(4-fluorophenyl)cyclohexyl]pyrrolidine are reported.

Nafion-Fe: A new efficient "green" lewis acid catalyst for the ketonic strecker reaction

The synthesis of various α-aminonitriles, precursors of α-amino acids has been carried out in moderate to high yields and high purity by the Strecker reaction from ketones, aliphatic/aromatic amines and TMSCN using a new "green" Lewis acid catalyst, Nafion-Fe (iron Nafionate, Fe(III) salt of Nafion-H, a solid polymeric perfluoroalkanesulfonic acid) under conventional thermal as well as microwave conditions. Microwave and solvent-free conditions applied in this method shorten the reaction times, improve the yields and diminishes the formation of side products. Strecker reaction occurs smoothly with secondary aliphatic amines also under these conditions which is not common under conventional conditions.

Heterogeneously catalysed Strecker-type reactions using supported Co(ii) catalysts: Microwave vs. conventional heating

A range of α-aminonitriles could be efficiently prepared from various aldehydes/ketones and primary or secondary amines using a highly active and stable Co(ii) complex supported on different mesoporous supports at both room temperature and low temperature microwave irradiation under solventless conditions. Catalysts were also highly reusable under the investigated reaction conditions and could be reused at least 10 times without loss of catalytic activity. The Royal Society of Chemistry.

Efficient Co(ii) heterogeneously catalysed synthesis of α-aminonitriles at room temperature via Strecker-type reactions

An environmentally friendly and highly active mesoporous Co(ii) complex on mesoporous SBA-15 material could be used as an easily recoverable catalyst for the synthesis of α-aminonitriles from a wide range of aldehydes/ketones and primary or secondary amines with good to excellent conversions yields at room temperature under solventless conditions. The catalyst can be recovered by simple filtration and could be reused at least 10 times without loss of catalytic activity.

A facile method for preparing aminobicyclo[n.1.0]alkane derivatives

The action of iodine on enamine (1) in the presence of anions, such as methoxide, cyanide, or succinimide ion, in methanol brings about an intramolecular cyclization and simultaneous substitution with these anions to give the corresponding aminobicyclo[n.1.0]alkane derivatives (2-4) in good yields.

Phencyclidine analogs for immunoassay

Novel analogs of phencyclidine (PCP) are disclosed. The analogs are capable of reacting with anti-PCT antibodies and are useful in immunoassays. The following analogs are described: STR1 wherein wherein X is --OH or a reporter molecule selected from the group consisting of aminofluorescein and aminomethylfluorescein and n is an integer between 1 and 10, inclusive.

Nickel catalysed coupling of allylamines and boronic acid

Allylamines function as substrates for cross-coupling with boronic acids in the presence of nickel(0) catalysts rather than palladium(0) catalysts.Aryl-, vinyl- and methyl-boronic acids function well.With vinyl derivatives, E-isomers couple more efficiently than Z-isomer and both fully retain the geometrical integrity.Methylations preferably employ the boronic esters like 2-methyl-1,3,2-benzodioxaborole or 2-methyl-1,3,2-dioxaborolane rather than methylboronic acid.The stereochemistry of the reaction involves a net inversion with respect to the allylamine.The regioselectivity is a function of ligand.Generally, sterically bulky donor phosphines promote new C-C bond formation at the less substituted position.Bidentate ligands, notably 1,1'-binaphthyl-2,2'-ylbis(diphenylphosphinite) (BINAPO), promote new C-C bond formation at the more substituted allyl terminus.The amines appear to be the preferred partner compared to allyl alcohols and esters with the boronic acids and give higher stereospecificity.