3306-69-2

Basic information

• Product Name: 2-azabicyclo[2.2.2]octan-3-one
• Synonyms: 2-azabicyclo[2.2.2]octan-3-one;Isonortropinone;Inchi=1/C7H11no/C9-7-5-1-3-6(8-7)4-2-5/H5-6H,1-4H2,(H,8,9;3-Isoquinuclidone;4-Aminocyclohexanecarboxylic acid lactam;NSC 85851
• CAS NO: 3306-69-2
• Molecular Formula: C₇H₁₁NO
• Molecular Weight: 125.17
• Mol File: 3306-69-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 200-202℃ (benzene hexane )
• Boiling Point: 297.4 °C at 760 mmHg
• Flash Point: 167.8 °C
• Appearance: /
• Density: 1.083 g/cm³
• Vapor Pressure: 0.00135mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 15.95±0.20(Predicted)
• CAS DataBase Reference: 2-azabicyclo[2.2.2]octan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-azabicyclo[2.2.2]octan-3-one(3306-69-2)
• EPA Substance Registry System: 2-azabicyclo[2.2.2]octan-3-one(3306-69-2)

Safety Data

• Hazardous Substances Data: 3306-69-2(Hazardous Substances Data)

Usage

Uses

2-Azabicyclo[2.2.2]octan-3-one (cas# 3306-69-2) is used in the preparation of quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or tyrosine kinases. It is also used in the preparation of phenyl derivatives containing inhibitors of coagulation factor for prophylaxis and/or therapy of thromboembolic disorders.

InChI:InChI=1/C7H11NO/c9-7-5-1-3-6(8-7)4-2-5/h5-6H,1-4H2,(H,8,9)

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 1776-53-0 4-aminocyclohexanecarboxylic acid 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 51498-33-0 ethyl 4-amino-1-cyclohexanecarboxylate 
• 61367-16-6 cis-4-aminocyclohexanecarboxylic acid methyl ester hydrochloride 
• 62456-15-9 methyl (1s,4s)-4-aminocyclohexane-1-carboxylate 
• 3685-23-2 cis-4-aminocyclohexane-1-carboxylic acid 

Downstream Products

• 74403-57-9 2-benzyl-2-aza-bicyclo[2.2.2]octan-3-one 
• 102012-20-4 2-benzhydryl-2-aza-bicyclo[2.2.2]octan-3-one 
• 1160928-97-1 2-phenyl-2-aza-bicyclo[2.2.2]octan-3-one 
• 444002-73-7 2-(4-nitrophenyl)-2-azabicyclo[2.2.2]octan-3-one 
• 132778-17-7 2-benzyl-2-methyl-2-azonia-bicyclo[2.2.2]octane; iodide 
• 102003-92-9 benzyl-cyclohex-3-enylmethyl-methyl-amine 
• 87640-24-2 cis-4-<(phenylmethyl)amino>cyclohexanecarboxylic acid 
• 102155-99-7 2-benzhydryl-2-aza-bicyclo[2.2.2]octane 

Relevant articles and documents

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Rapid and Mild Lactamization Using Highly Electrophilic Triphosgene in a Microflow Reactor

Lactams are cyclic amides that are indispensable as drugs and as drug candidates. Conventional lactamization includes acid-mediated and coupling-agent-mediated approaches that suffer from narrow substrate scope, much waste, and/or high cost. Inexpensive, less-wasteful approaches mediated by highly electrophilic reagents are attractive, but there is an imminent risk of side reactions. Herein, a methods using highly electrophilic triphosgene in a microflow reactor that accomplishes rapid (0.5–10 s), mild, inexpensive, and less-wasteful lactamization are described. Methods A and B, which use N-methylmorpholine and N-methylimidazole, respectively, were developed. Various lactams and a cyclic peptide containing acid- and/or heat-labile functional groups were synthesized in good to high yields without the need for tedious purification. Undesired reactions were successfully suppressed, and the risk of handling triphosgene was minimized by the use of microflow technology.

COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF

Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

An improved preparation of 2-azabicyclo[2.2.2]octane

An improved preparative four-step synthesis to isoquinuclidine tosylate salt 4 has been demonstrated in 70% overall yield from p-aminobenzoic acid (PABA) 1. Hydrogenation of PABA 1 affords 4-aminocyclohexane carboxylic acid 2 as an 80 : 20 mixture of cis- and trans-isomers. Heating the mixture at 250°C effected epimerization and cyclization to provide the bicyclic lactam 3. Subsequent Red-A1 reduction and treatment with tosic acid furnished the desired bicyclic amine, tosylate salt 4.