5263-68-3

Basic information

• Product Name: (1R,2S,6R,7S)-4-azatricyclo[5.2.1.0~2,6~]dec-8-ene
• Synonyms: (1R,2S,6R,7S)-4-azatricyclo[5.2.1.0~2,6~]dec-8-ene;2-Azadicyclopentadiene, 2,3-dihydro-;(3aR,4S,7R,7aS)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindole
• CAS NO: 5263-68-3
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• Mol File: 5263-68-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 205.3°Cat760mmHg
• Flash Point: 77.5°C
• Appearance: /
• Density: 1.049g/cm³
• Vapor Pressure: 3.5E-09mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: (1R,2S,6R,7S)-4-azatricyclo[5.2.1.0~2,6~]dec-8-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,6R,7S)-4-azatricyclo[5.2.1.0~2,6~]dec-8-ene(5263-68-3)
• EPA Substance Registry System: (1R,2S,6R,7S)-4-azatricyclo[5.2.1.0~2,6~]dec-8-ene(5263-68-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5263-68-3(Hazardous Substances Data)

Usage

General Description

The chemical (1R,2S,6R,7S)-4-azatricyclo[5.2.1.0~2,6~]dec-8-ene, also known as quinuclidine, is a bicyclic amine compound with a molecular formula of C7H13N. It is a colorless liquid with a pungent odor and is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and specialty chemicals. Quinuclidine is also used as a catalyst in organic reactions and as a solvent in chemical processes. It is flammable and may cause skin and eye irritation, and has potential health hazards if inhaled or ingested. Overall, quinuclidine is a versatile molecule with a variety of industrial applications.

InChI:InChI=1/C17H18ClN3O2/c18-17-7-6-16(21(22)23)12-14(17)13-19-8-10-20(11-9-19)15-4-2-1-3-5-15/h1-7,12H,8-11,13H2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 61800-55-3 endo-5-carbamoylbicyclo[2.2.1]hept-2-ene-endo-6-carboxylic acid 
• 6265-30-1 (1R,2S,6R,7S)-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione 

Downstream Products

• 521301-28-0 N-(p-tolylsulfonyl)-4-azatricyclo[5.2.1.0^2,6]dec-8-ene 
• 936747-84-1 C₃₃H₃₂O₃N₂ 
• 1356691-52-5 (1S,3aR,4S,7R,7aS)-N-benzyl-2-(pyrimidin-2-yl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindole-1-carbothioamide 
• 1356691-43-4 (1S,3aR,4S,7R,7aS)-N-benzyl-2-(4-nitrophenyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindole-1-carboxamide 
• 1356691-40-1 (1S,3aR,4S,7R,7aS)-N-(tert-butyl)-2-(4-nitrophenyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindole-1-carboxamide 
• 1356691-38-7 (1S,3aR,4S,7R,7aS)-N-benzyl-2-(2-nitrophenyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindole-1-carboxamide 
• 1356691-36-5 (1S,3aR,4S,7R,7aS)-N-isopropyl-2-(2-nitrophenyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindole-1-carboxamide 
• 1356691-35-4 (1S,3aR,4S,7R,7aS)-N-(tert-butyl)-2-(2-nitrophenyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindole-1-carboxamide 
• 1356691-60-5 (1S,3aR,4S,7R,7aS)-N-(2-nitrophenyl)-2-((R)-1-phenylethyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindole-1-carboxamide 

Relevant articles and documents

IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel-Crafts reactions

The first o-iodoxybenzoic acid (IBX) mediated oxidation of unactivated amines to imines is described. A range of meso-pyrrolidines were shown to be suitable substrates. The chemical space was further explored with one-pot oxidative Ugi-type and aza-Friedel-Crafts reactions, which proved to be highly diastereoselective.

Ring-opening Cross-metathesis (ROCM) as a novel tool for the ligation of peptides

The development of ring-opening cross-metathesis (ROCM) as a novel tool for the site-specific ligation of peptide units is reported. The resulting structural units at the site of ligation resulting from ROCM resemble proline as well as other known ss-turn

Synthesis, structure, and transformations of new endic anhydride derivatives

4-Azatricyclo[5.2.1.02,6]dec-8-ene and its N-phenyl derivative were synthesized by reaction of endic anhydride with amines, transformation of the amido acids thus obtained to imides, and subsequent reduction of the latter with lithium aluminum hydride. The unsubstituted tricyclic amine was brought into reactions with electrophilic reagents: p-toluenesulfonyl chloride, p-toluoyl chloride, m-tolyl isocyanate, phenyl isothiocyanate, and endic anhydride to obtain a number of new derivatives; also, the corresponding salt with 1-adamantanecarboxylic acid was isolated. N-(p-Tolylsulfonyl)- and N-(m-tolylcarbamoyl)-4-azatricyclo[5.2.1.02,6]dec-8-enes were oxidized to the corresponding 8,9-epoxy derivatives with monoperoxyphthalic acid. The structure of the products was confirmed by the data of IR, 1H and 13C NMR, and mass spectra. The molecular structures of N-(p-iodophenyl)bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboximide and N-phenyl-4-azatricyclo[5.2.1.02,6]dec-8-ene were established by X-ray analysis.