1-Azabicyclo[2.2.1]heptan-3-one

Base Information

• Chemical Name: 1-Azabicyclo[2.2.1]heptan-3-one
• CAS No.: 21472-89-9
• Molecular Formula: C6H9NO
• Molecular Weight: 111.144
• Hs Code.: 2933990090
• European Community (EC) Number: 878-535-1
• UNII: H2Q2DRD4KG
• DSSTox Substance ID: DTXSID90864991
• Nikkaji Number: J83.077A
• Mol file: 21472-89-9.mol

Synonyms:1-azabicyclo[2.2.1]heptan-3-one;21472-89-9;1-Aza-bicyclo[2.2.1]heptan-3-one;H2Q2DRD4KG;(1S,4R)-1-Azabicyclo[2.2.1]heptan-3-one;1-Azabicyclo(2.2.1)heptan-3-one;1-azabicyclo (2.2.1] heptan-3-one;1-azabicyclo [2.2.1] heptan-3-one;142034-96-6;UNII-H2Q2DRD4KG;SCHEMBL700655;SCHEMBL8201191;DTXSID90864991;VZPRMKOCTSUHCR-UHFFFAOYSA-N;BCP27000;MFCD11506690;AKOS015855490;AB92110;(+/-)1-azabicyclo [2.2.1]heptan-3-one;AM20090192;CS-0106909;FT-0734055;EN300-98246;D76671

Chemical Property of 1-Azabicyclo[2.2.1]heptan-3-one

Chemical Property:

• Vapor Pressure: 0.754mmHg at 25°C
• Refractive Index: 1.541
• Boiling Point: 183.871 °C at 760 mmHg
• Flash Point: 72.656 °C
• PSA: 20.31000
• Density: 1.175 g/cm³
• LogP: -0.17110
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 111.068413911
• Heavy Atom Count: 8
• Complexity: 133

Purity/Quality:

97% ^*data from raw suppliers

1-azabicyclo[2.2.1]heptan-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CC1C(=O)C2
• Uses: 1-Azabicyclo[2.2.1]heptan-3-one (CAS# 21472-89-9) can be used in the preparation of spirocyclic quinuclidinyl-Δ2-isoxazolines as neuronal nicotinic acetylcholine receptor agonists. It can also be used in the preparation of isoquinoline derivatives as progranulin modulators useful in treatment of progranulin-associated disorders. Useful in the preparation of N-pyridinyl carboxamides as cyclin-dependent kinase inhibitors. Useful in the preparation of glucosylceramide synthase inhibitors for treatment of metabolic diseases, such as lysosomal storage diseases.

Technology Process of 1-Azabicyclo[2.2.1]heptan-3-one

There total 5 articles about 1-Azabicyclo[2.2.1]heptan-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: 75.0%

(1S)-(+) azabicyclo[2,2,1]hept-5-ene-3-one → 1-azabicyclo[2.2.1]heptan-3-one (21472-89-9)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; for 5h; under 2585.81 Torr; in a Parr Hydrogenation Apparatus;

Reference yield: 36.0%

1-<(ethoxycarbonyl)methyl>-3-(methoxycarbonyl)pyrrolidine (142483-57-6) → 1-azabicyclo[2.2.1]heptan-3-one (21472-89-9)

Guidance literature:

With potassium tert-butylate; In toluene; for 2h; Heating;

DOI:10.1021/jm00091a007

Reference yield: 27.0%

methyl 1-(2-methoxy-2-oxoethyl)pyrrolidine-3-carboxylate (121564-87-2) → 1-azabicyclo[2.2.1]heptan-3-one (21472-89-9)

Guidance literature:

methyl 1-(2-methoxy-2-oxoethyl)pyrrolidine-3-carboxylate; With potassium tert-butylate; In toluene; for 4h; Reflux;

With hydrogenchloride; In water; at 110 ℃; for 8h;

upstream raw materials:

methyl 1-(2-methoxy-2-oxoethyl)pyrrolidine-3-carboxylate

1-<(ethoxycarbonyl)methyl>-3-(methoxycarbonyl)pyrrolidine

methyl 1-(2-methoxy-2-oxoethyl)-5-oxopyrrolidine-3-carboxylate

Downstream raw materials:

exo-3-hydroxy-endo-3-methoxycarbonyl-1-azabicyclo<2.2.1>heptane

endo-3-hydroxy-exo-3-methoxycarbonyl-1-azabicyclo<2.2.1>heptane

2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one

2-(1-naphthylmethylene)-3-quinuclidinone