167562-95-0

Basic information

• Product Name: 7-Azabicyclo[2.2.1]hept-2-ene-7-carboxylic acid, 2-[(4-methylphenyl)sulfonyl]-, 1,1-dimethylethyl ester
• CAS NO: 167562-95-0
• Molecular Formula: C18H23NO4S
• Molecular Weight: 349.451
• Mol File: 167562-95-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 7-Azabicyclo[2.2.1]hept-2-ene-7-carboxylic acid, 2-[(4-methylphenyl)sulfonyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Azabicyclo[2.2.1]hept-2-ene-7-carboxylic acid, 2-[(4-methylphenyl)sulfonyl]-, 1,1-dimethylethyl ester(167562-95-0)
• EPA Substance Registry System: 7-Azabicyclo[2.2.1]hept-2-ene-7-carboxylic acid, 2-[(4-methylphenyl)sulfonyl]-, 1,1-dimethylethyl ester(167562-95-0)

Safety Data

• Hazardous Substances Data: 167562-95-0(Hazardous Substances Data)

Upstream product

• 6018-89-9 nickel(II) acetate tetrahydrate 
• 160732-46-7 endo-2-(p-tolyl-sulfone)-7-tert-butoxycarbonyl-7-azabicyclo<2.2.1>hepta-2,5-diene 
• 98-59-9 p-toluenesulfonyl chloride 
• 34452-56-7 trimethylsilyl p-tolylsulfonylacetylene 
• 13894-21-8 ethynyl p-tolyl sulfone 
• 5176-27-2 N-tert-butyloxycarbonyl-pyrrole 

Relevant articles and documents

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Synthesis of a fluorine-18 labeled derivative of epibatidine for in vivo nicotinic acetylcholine receptor PET imaging

Epibatidine (exo-2-(2'-chloro-5'-pyridyl)-7-azabicyclo[2.2.1]heptane), a natural compound isolated from the skin of the Ecuadorian poison frog Epipedobates tricolor, is the most potent nicotinic acetylcholine receptor (nAChR) agonist reported to date. In order to visualize and quantify in vivo these receptors in human brain using Positron Emission Tomography (PET), [18F]norchlorofluoroepibatidine (exo-2-(2'-[18F]fluoro-5'-pyridyl)-7-azabicyclo[2.2.1]heptane), a fluorine-18 (t(1/2): 110min) radiolabeled derivative of epibatidine has been designed. The corresponding 2'-bromo-, 2'-iodo- and 2'-nitro exo-2-(5'-pyridyl)-7-azabicyclo[2.2.1]heptane analogues as labeling precursors, as well as norchlorofluoroepibatidine as a reference compound have been synthesized by reductive, stereoselective, palladium-catalyzed Heck-type coupling between an N-Boc protected azanorbornene and the corresponding halopyridine. [18F]Norchlorofluoroepibatidine has been radiolabeled with fluorine-18 by nucleophilic aromatic substitution from the corresponding Boc-protected halo- and nitro precursors using [18F]FK-K222 complex in DMSO by conventional heating (at 150-180°C for 10min) or microwave activations (at 100 Watt, for 1 to 2.5min), followed by TFA-removal of the protective group. Typically, using the microwave activation procedure, 60-80mCi (2.22-2.96 GBq) of pure [18F]norchlorofluoroepibatidine could be obtained in less than 2h (110-115min) from the bromo labeling precursor, with specific radioactivities of 1.5-2.5Ci/μmol (55.5-92.5GBq/μmol) calculated for End of Bombardment. The preliminary PET experiments in baboon (Papio papio) with [18F]norchlorofluoroepibatidine show a high uptake and a rapid accumulation of the radiotracer into the brain within 30min. In the thalamus, a nAChR rich area, uptake of radioactivity reached a maximum at 40min (10% I.D./100mL tissue). The ratio of radioactivity thalamus/cerebellum (the latter being a nAChR poor area) was 2 at 40min and increased with time, up to 4.3 at 160min. Its specific regiodistribution and its high ratio of specific-to-nonspecific binding confirm the ideal profile of [18F]norchlorofluoroepibatidine as a suitable radioligand for PET imaging of nAChRs in the brain. Copyright (C) 1999 Elsevier Science Ltd.

Synthesis and nicotinic acetylcholine receptor binding properties of exo-2-(2'-fluoro-5'-pyridinyl)-7-azabicyclo-[2.2.1]heptane: A new positron emission tomography ligand for nicotinic receptors

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