125736-03-0

Basic information

• Product Name: 9-(tert-butoxycarbonyl)-9-azabicyclo[4.2.1]nonane-2-carboxylic acid
• CAS NO: 125736-03-0
• Molecular Formula: C₁₄H₂₃NO₄
• Molecular Weight: 269.3367
• Mol File: 125736-03-0.mol

Chemical Properties

• Boiling Point: 400.9°C at 760 mmHg
• Flash Point: 196.2°C
• Density: 1.165g/cm³
• Vapor Pressure: 1.51E-07mmHg at 25°C
• Refractive Index: 1.512
• CAS DataBase Reference: 9-(tert-butoxycarbonyl)-9-azabicyclo[4.2.1]nonane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(tert-butoxycarbonyl)-9-azabicyclo[4.2.1]nonane-2-carboxylic acid(125736-03-0)
• EPA Substance Registry System: 9-(tert-butoxycarbonyl)-9-azabicyclo[4.2.1]nonane-2-carboxylic acid(125736-03-0)

Safety Data

• Hazardous Substances Data: 125736-03-0(Hazardous Substances Data)

Upstream product

• 125736-02-9 C₂₀H₃₇NO₄Si 
• 112020-13-0 2-acetyl-9-(tert-butoxycarbonyl)-9-azabicyclo<4.2.1>nonane 
• 125736-06-3 (1R,2R)- and (1R,2S)-9-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-9-azabicyclo<4.2.1>nonane 
• 129001-05-4 C₁₇H₂₇NO₄S₂ 
• 125736-00-7 (1R,2S,6R)-2-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester 

Downstream Products

• 125736-06-3 (1R,2S,6R)-9-Aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-tert-butyl ester 2-methyl ester 
• 129001-06-5 (R)-2-Chlorocarbonyl-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester 
• 90741-49-4 (R)-2-Acetyl-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester 

Relevant articles and documents

Enantiodivergent Synthesis of (+)- and (-)-Anatoxin from L-Glutamic acid

The optically pure 2,5-difunctionalized homotropane 11, prepared from L-glutamic acid, serves as the common, advanced intermediate for the synthesis of either natural (+)-anatoxin (30, 18percent overall yield) or unnatural (-)-anatoxin (33, 30percent overall yield) by selective manipulation of either the C-2 ester or C-5 acetyl functionalities.Side-chain substitution in the decarbonylative iminium ion cyclization of a substituted proline enhanced the yield by 25percent as compared to the unsubstituted parent system.The additional substitution at C-5 of the 9-azabicyclononane ring system allows access to analogues of anatoxin not availalble through other syntheses.

Chirospecific Syntheses of Nitrogen and Side-Chain Modified Anatoxin Analogues. Synthesis of (1R)-Anatoxinal and (1R)-Anatoxinic Acid Derivatives

A straightforward and good yielding route to side-chain analogues of the potent neurotoxin and neurotransmitter (+)-anatoxin (1) has been developed.Peroxy acid oxidation of the (silyloxy)butadiene 43 derived from readily synthesized, optically pure (1R)-t-BOC-anatoxin (42) affords silyloxy ketone 44.Fluorolysis of 44 followed by oxidative cleavage of the resultant α-hydroxy ketone 45 gives a mixture of α,β-unsaturated acid 46 and ester 41 in 57percent combined yield.Other approaches to these compounds, based on literature precedent, failed. (1R)-t-BOC-anatoxinic acid (46) then serves as educt for the synthesis of a wide variety of anatoxin derivatives with modified side-chain functionality.These analogues, designed to serve as probes of the antagonist binding site of the nicotinic acetylcholine receptor, include alcohol, aldehyde, amide, hydroxamate, and oxime ether functional groups.