114704-10-8

Basic information

• Product Name: 1-Azabicyclo[2.2.1]heptane-3-carboxylic acid, ethyl ester
• Synonyms: 1-Azabicyclo[2.2.1]heptane-3-carboxylic acid, ethyl ester
• CAS NO: 114704-10-8
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.2209
• Mol File: 114704-10-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Azabicyclo[2.2.1]heptane-3-carboxylic acid, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azabicyclo[2.2.1]heptane-3-carboxylic acid, ethyl ester(114704-10-8)
• EPA Substance Registry System: 1-Azabicyclo[2.2.1]heptane-3-carboxylic acid, ethyl ester(114704-10-8)

Safety Data

• Hazardous Substances Data: 114704-10-8(Hazardous Substances Data)

Usage

Type of compound

Synthetic organic compound

Usage

Building block in the synthesis of various pharmaceuticals and agrochemicals

Derivative of

Azabicyclo[2.2.1]heptane

Bicyclic compound

Contains a nitrogen atom in the ring

Ester group

Ethyl ester

Solubility

More easily soluble in organic solvents

Hazardous nature

Not considered to be hazardous

Application

Commonly used in research and development in the pharmaceutical and agrochemical industries

Upstream product

• 133366-42-4 cis-2-benzylhexahydropyrano<3,4-c>pyrrol-4(3aH)-one 
• 115594-43-9 (1R,3R,4S)-1-Benzyl-3-ethoxycarbonyl-1-azonia-bicyclo[2.2.1]heptane; bromide 
• 3393-45-1 5,6-dihydro-pyran-2-one 
• 133745-55-8 (3R,4S)-1-Benzyl-4-(2-bromo-ethyl)-pyrrolidine-3-carboxylic acid ethyl ester; hydrobromide 
• 133745-58-1 (1R,3S,4S)-1-Benzyl-3-ethoxycarbonyl-1-azonia-bicyclo[2.2.1]heptane; bromide 
• 5657-52-3 1,3-dihydrofuro<3,4-c>pyridin-3-one 
• 4664-08-8 cinchomeronic anhydride 
• 133745-54-7 cis-5-benzyl-3a,4,5,6,7,7a-hexahydrofuro<3,4-c>pyridin-3(1H)-one 
• 133745-56-9 (3S,4S)-1-Benzyl-4-bromomethyl-piperidine-3-carboxylic acid ethyl ester 
• 72726-63-7 4-(Hydroxymethyl)nicotinic acid 
• 118796-92-2 Hexahydro-furo[3,4-c]pyridin-3-one 
• 118796-92-2 (3aR,7aR)-Hexahydro-furo[3,4-c]pyridin-3-one 

Downstream Products

• 115595-00-1 (1R,3S,4R)-1-Aza-bicyclo[2.2.1]heptane-3-carboxylic acid 
• 130513-77-8 (1R,3S,4R)-1-Aza-bicyclo[2.2.1]heptane-3-carbonyl chloride 
• 123916-90-5 endo-3-acetyl-1-azabicyclo<2.2.1>heptane 
• 121564-88-3 exo-methyl 1-azabicyclo<2.2.1>heptane-3-carboxylate 
• 115595-00-1 (1S,3S,4S)-1-Aza-bicyclo[2.2.1]heptane-3-carboxylic acid 
• 130513-77-8 (1S,3S,4S)-1-Aza-bicyclo[2.2.1]heptane-3-carbonyl chloride 
• 121564-89-4 exo-3-(3-methyl-1,2,4-oxadiazol-5-yl)-1-azabicyclo<2.2.1>heptane 

Relevant articles and documents

Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl- based muscarinic receptor ligands has been studied, and the exo- azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.

Diastereoselective routes toendo andexo ethyl 1-azabicyclo[2.2.1] hept-3-YL carboxylates

Diastereoselective routes to endo and exo ethyl 1-azabicyclo[2.2.1]hept-3-yl carboxylates (1) and (2) based on the hydrogen bromide cleavage of the isomeric [4.3.0] bicyclic cis fused lactones (3) and (4) are described.