6945-87-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-2-cyano-bicyclo(2,2,1)-hept-5-ene is used as an intermediate in the synthesis of various pharmaceuticals due to its unique structural properties, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2-CHLORO-2-CYANO-BICYCLO(2,2,1)-HEPT-5-ENE also serves as an intermediate in the synthesis of agrochemicals, playing a crucial role in the development of effective pesticides and other agricultural chemicals to enhance crop protection and yield.
Used in Specialty Polymers Production:
2-Chloro-2-cyano-bicyclo(2,2,1)-hept-5-ene is utilized as a building block in the production of specialty polymers, which have specific properties tailored for use in various industries, including automotive, aerospace, and electronics.
Used in Organic Compounds Synthesis:
As a versatile chemical building block, 2-chloro-2-cyano-bicyclo(2,2,1)-hept-5-ene is employed in the synthesis of other organic compounds, expanding the range of chemical products available for various applications across different industries.

InChI:InChI=1/C8H8ClN/c9-8(5-10)4-6-1-2-7(8)3-6/h1-2,6-7H,3-4H2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 920-37-6 2-Chloroacrylonitrile 
• 77-73-6 bi(cyclopentadiene) 
• 2890-96-2 5-norbornene-2-carbonitrile 

Downstream Products

• 83205-33-8 (1S,2S,4R,5S,6S)-2,5-Dichloro-6-phenylselanyl-bicyclo[2.2.1]heptane-2-carbonitrile 
• 83205-33-8 6-exo-benzeneselenenyl-2-endo,5-endo-dichlorobicyclo<2.2.1>heptane-2-exo-carbonitrile 
• 694-98-4 norborn-5-en-2-one 
• 125107-71-3 ((1R,2S,6S,7R)-3,5-Dioxo-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-1-yl)-acetonitrile 
• 125107-72-4 ((1R,2R,6S,7S,10R)-3,5-Dioxo-4-phenyl-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-10-yl)-acetonitrile 
• 497-38-1 2-norbornanone 

Relevant academic research and scientific papers

Microwave-assisted solvent-free Diels-Alder reaction - A fast and simple route to various 5,6-substituted norbornenes and polychlorinated norbornenes

A series of 5,6-substituted norbornenes and 5,6-substituted polychlorinated norbornenes was prepared by using a microwave-assisted Diels-Alder reaction. This procedure proved very versatile, fast, and with an easy workup step, and therefore suitable even for large-scale synthesis. Georg Thieme Verlag Stuttgart · New York.

Metalated nitrile and enolate chlorinations

(Figure presented) Metalated nitriles and enolates rapidly and efficiently abstract chlorine from 2-chloro-2-fluoro-2-phenylacetonitrile to afford a diverse range of chloronitriles and chloroesters. The method provides the first general anionic chlorinati

Ring-rearrangement metathesis of substituted 2-aminonorbornenes

In this report we describe the ring-rearrangement metathesis of 2-aminonorbornene derivatives. An efficient ruthenium-catalysed metathesis reaction occurs with a wide range of pendent alkenes and alkynes to generate bicyclic amines and amides. Georg Thieme Verlag Stuttgart.

2-Chlorobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2-chlorobicyclo[2.2.1] heptane-2-carboxamide as precursors of bicyclo[2.2.1]hept-5-en-2-one and bicyclo[2.2.1]heptan-2-one: Resolution, absolute configuration and hydrogen-bonding properties

The absolute configuration of bicyclo[2.2.1]heptan-2-one has not been correlated with a crystal structure of a chemical precursor. The only chemical correlation available had an ambiguity, which could have reversed the assignment. Herein, we report the resolution of 2-chlorobicyclo[2.2.1]hept-5-en- 2-exo-carboxamide on a cellulose triacetate column and the crystal structures of the enantiomerically pure and racemic α-chloroamide. We found the absolute configuration (1R,2R,4R) for the (+)-enantiomer of the α-chloroamide. This compound was converted to (+)-bicyclo[2.2.1]hept-5- ene-2-one by base hydrolysis, and the 5,6-unsaturated compounds converted to the saturated congeners. This is the first unambiguous experimental determination of the absolute configuration of bicyclo[2.2.1]heptan-2-one and of bicyclo[2.2.1]hept-5-ene-2-one. The three crystal structures of 2-chlorobicyclo[2.2.1]hept-5-en-2-exo-carboxamide reported herein reveal H-bonded dimers, with two distinct orientations of the bicyclic portion relative to the carboxamide dimer. In the racemic crystal, each dimer is composed of two enantiomers, and the bicyclic portions have their bridge carbon atom (C-7) on opposite sides of the H-bonded carboxamide dimer moiety. In the enantiomerically pure crystals, the major dimer had both C-7 atoms on the same side of the carboxamide dimer moiety while the minor dimer had the C-7 atoms on opposite sides. The dimers are present in solution, and can be easily monitored.

PHARMACEUTICAL COMPOSITIONS AND METHODS FOR RELIEVING PAIN AND TREATING CENTRAL NERVOUS SYSTEM DISORDERS

Patients susceptible to or suffering from disorders, such as central nervous system disorders, which are characterized by an alteration in normal neurotransmitter release, such as dopamine release (e.g., Parkinsonism, Parkinson's Disease, Tourette's Syndrome, attention deficient disorder, or schizophrenia), are treated by administering a compound of Formulas (1 or 2), as described herein. The compounds of Formulas (1 and 2) are also useful for treating pain, and treating drug addiction, nicotine addiction, and/or obesity. The compounds can exist as individual stereoisomers, racemic mixtures, diastereomers and the like.

ADDITION OF MOLECULAR FLUORINE TO BICYLCOHEPT-2-ENE DERIVATIVES AND CONVERSION TO FLUORINE-CONTAINING CARBOCYCLIC NUCLEOSIDES

Addition of molecular fluorine to bicyclohept-2-ene derivatives has been found to give exo,exo-difluoro adducts in fair yields.The difluoro adduct (13c) was converted to the fluorine containing carbocyclic adenosine and guanosine analogs.

Acid-Catalyzed Hydrolysis of Bridged Bi- and Tricyclic Compounds. XXVI. The Mechanisms of Formation of the Hydration Products of 2-Norbornen-5-one

The acid-catalyzed hydration of 2-norbornen-5-one (1) in 5 mol dm-3 HClO4 at 358 K produces, according to GLC analyses, exo-5-hydroxy-2-norbornanone (2), 2-oxabicycloctan-3-one (3), which is in equilibrium with cis-3-hydroxycyclopentaneacetic acid (5), and 2-oxabicyclooctan-3-one (4).The former lactone (3) is unstable and rearranges slowly to the latter (4).The ketoalcohol (2) is formed via the slow protonation of norbornenone at C(3) and via subsequent hydration of the carbocation.The lactones are formed via complicated routes started by the protonation of norbornenone at C(2), and comprising 3- and 2-cyclopentaneacetic acid (7 and 9) as unstable intermediate products.

Aliphatic diazo compounds. XIV. The synthesis of 7-substituted 3-diazo-2-norbornanones and the infrared and proton and carbon-13 nuclear magnetic resonance spectra of these diazo ketones and their precursors

syn and anti-7-Isopropyl-2-norbornanone (5 and 6) were prepared by catalitic hydrogenation of 7-isopropylidene-2-norbornanone; syn and anti-7-benzhydryl-2-norbornane (9 and 10) were prepared in analogous fashion.Ketones 5 and 6 and syn- and anti-7-tert-bu

A serendipitous, high yield conversion of norbornenone to tricyclo2,7>octan-4-one

Simmons-Smith cyclopropanation of the trimethylsilyl enol ether of norbornenone has been found to generate the 2-trimethylsilyl ether of homoquadricyclene, homoketonization of which affords the symmetrical tricyclo2,7>octan-4-one regiospecifically with high stereoselectivity favoring inversion of configuration.

Efficient Stereocontrolled Total Syntheses of Racemic and Natural Brefeldin-A

Brefeldin-A, an antiobiotic fungal metabolite, has been obtained in both racemic and natural forms through a direct approach that employs norbornenone and 6-heptyn-2-ol as the basic starting materials.