2-Azabicyclo[2.2.2]octan-3-one

Base Information

• Chemical Name: 2-Azabicyclo[2.2.2]octan-3-one
• CAS No.: 3306-69-2
• Molecular Formula: C7H11NO
• Molecular Weight: 125.17
• Hs Code.: 2933790090
• European Community (EC) Number: 830-572-4
• NSC Number: 85851
• DSSTox Substance ID: DTXSID60186718
• Nikkaji Number: J12.864C
• Wikidata: Q72444273
• Mol file: 3306-69-2.mol

Synonyms:2-Azabicyclo[2.2.2]octan-3-one;3306-69-2;3-Isoquinuclidone;Isonortropinone;Cyclohexanecarboxylic acid, 4-amino-, lactam;2-Azabicyclo[2,2,2]octan-3-one;(1S,4S)-2-AZABICYCLO[2.2.2]OCTAN-3-ONE;3-azabicyclo[2.2.2]octan-2-one;4-Aminocyclohexanecarboxylic acid lactam;NCIOpen2_001018;SCHEMBL85907;SCHEMBL10474079;DTXSID60186718;Cyclohexanecarboxylic acid, lactam;CZVSOFLNEUYJRJ-UHFFFAOYSA-N;NSC85851;MFCD16547516;NSC 85851;NSC-85851;STL453938;2-Aza-bicyclo[2.2.2]octan-3-one;AKOS005166893;AKOS006357059;PB30124;AMY202100070;AS-34454;CS-15839;CS-0052042;FT-0654027;(1r,4r)-2-azabicyclo[2.2.2]octan-3-one;EN300-59958;EN300-399459;EN300-2985024;A821601;Z926909656;InChI=1/C7H11NO/c9-7-5-1-3-6(8-7)4-2-5/h5-6H,1-4H2,(H,8,9

Chemical Property of 2-Azabicyclo[2.2.2]octan-3-one

Chemical Property:

• Vapor Pressure: 0.00135mmHg at 25°C
• Melting Point: 200-202℃ (benzene hexane )
• Refractive Index: 1.497
• Boiling Point: 297.4 °C at 760 mmHg
• PKA: 15.95±0.20(Predicted)
• Flash Point: 167.8 °C
• PSA: 29.10000
• Density: 1.083 g/cm³
• LogP: 1.00380
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 125.084063974
• Heavy Atom Count: 9
• Complexity: 136

Purity/Quality:

98% ^*data from raw suppliers

2-Azabicyclo[2.2.2]octan-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CCC1C(=O)N2
• 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.

Technology Process of 2-Azabicyclo[2.2.2]octan-3-one

There total 13 articles about 2-Azabicyclo[2.2.2]octan-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

4-aminocyclohexanecarboxylic acid (1776-53-0) → 2-aza-bicyclo[2.2.2]octan-3-one (3306-69-2)

Guidance literature:

With diphenyl ether-biphenyl eutectic; at 250 ℃;

DOI:10.1081/SCC-120004848

Reference yield: 89.0%

C7H12NO2(1-)*K(1+) → 2-aza-bicyclo[2.2.2]octan-3-one (3306-69-2)

Guidance literature:

With 1-methyl-1H-imidazole; bis(trichloromethyl) carbonate; potassium hydroxide; In water; acetonitrile; at 60 ℃; for 0.00277778h; Inert atmosphere;

DOI:10.1002/chem.202100059

Reference yield: 86.3%

cis-4-aminocyclohexylcarboxylic acid → 2-aza-bicyclo[2.2.2]octan-3-one (3306-69-2)

Guidance literature:

at 290 ℃; for 0.25h;

upstream raw materials:

4-aminocyclohexanecarboxylic acid

cis-4-aminocyclohexane-1-carboxylic acid

methyl (1s,4s)-4-aminocyclohexane-1-carboxylate

4-amino-benzoic acid

Downstream raw materials:

2-benzyl-2-aza-bicyclo[2.2.2]octan-3-one

2-benzhydryl-2-aza-bicyclo[2.2.2]octan-3-one

2-benzyl-2-aza-bicyclo[2.2.2]octane

2-benzhydryl-2-aza-bicyclo[2.2.2]octane

Refernces

• 1、 Augustine,Vag. "-". . p. 1074. Retrieved 1975.
• 2、 -. "COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF". Page/Page column 175. . Retrieved 2011/07/07.
• 3、 He, Wei,Myers, Michael R.,Hanney, Barbara,Spada, Alfred P.,Bilder, Glenda,Galzcinski, Helen,Amin, Dilip,Needle, Saul,Page, Ken,Jayyosi, Zaid,Perrone, Mark H.. "Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 2: The synthesis and biological activities of RPR127963 an orally bioavailable inhibitor". . p. 3097 - 3100. Retrieved 2007/10/03.