1-Benzylazetidin-2-one

Base Information

• Chemical Name: 1-Benzylazetidin-2-one
• CAS No.: 4458-64-4
• Molecular Formula: C10H11NO
• Molecular Weight: 161.203
• DSSTox Substance ID: DTXSID20456500
• Nikkaji Number: J575.999D
• Wikidata: Q82279033
• Mol file: 4458-64-4.mol

Synonyms:1-benzylazetidin-2-one;4458-64-4;1023281-96-0;2-Azetidinone, 1-(phenylmethyl)-;N-benzyl beta-lactam;N-benzyl-2-azetidinone;1-benzyl-2-azetidinone;1-benzyl-azetidin-2-one;SCHEMBL7389188;DTXSID20456500;FYLYJFHGDNQLJJ-UHFFFAOYSA-N;AKOS015907318;SB51919;A826631

Chemical Property of 1-Benzylazetidin-2-one

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 161.084063974
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(C1=O)CC2=CC=CC=C2

Technology Process of 1-Benzylazetidin-2-one

There total 25 articles about 1-Benzylazetidin-2-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: 96.0%

N-benzyl-β-alanine (5426-62-0) → N-benzyl-2-azetidinone (4458-64-4)

Guidance literature:

With tris(2-oxo-3-oxazolinyl)phosphine oxide; triethylamine; In acetonitrile; for 6h; Heating;

DOI:10.1016/S0040-4039(00)86712-X

Reference yield: 90.0%

ethyl-3-benzylamino propionate (23583-21-3) → N-benzyl-2-azetidinone (4458-64-4)

Guidance literature:

With bis(bis(trimethylsilyl)amido)tin(II); In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1021/ja00074a007

Reference yield: 86.0%

β-bromopropionic acid N-benzylamide (1665-47-0) → N-benzyl-2-azetidinone (4458-64-4)

Guidance literature:

With potassium hydroxide; tetrabutylammomium bromide; In dichloromethane; for 6.5h; Ambient temperature;

upstream raw materials:

β-bromopropionic acid N-benzylamide

ethyl-3-benzylamino propionate

ethylmagnesium bromide

N-benzyl-β-alanine

Downstream raw materials:

1-benzyl-4-methoxyazetidin-2-one

1-(α-methoxybenzyl)azetidin-2-one

caprolactam

N-benzyl 3-methylthiopropionamide

Refernces

• 1、 Jang, Yujin,Johnson, J. Drake,Jung, Myunggi,Lindsay, Vincent N. G.,Poteat, Christopher M.,Williams, Rachel G.. "Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β-Lactams". supporting information. p. 18655 - 18661. Retrieved 2020/08/21.
• 2、 Hermant, Fabien,Urbaska, Ewelina,Seizilles De Mazancourt, Sarah,Maubert, Thomas,Nicolas, Emmanuel,Six, Yvan. "Reductive alkylation of thioamides with Grignard reagents in the presence of Ti(O i Pr)4: Insight and extension". supporting information. p. 5643 - 5653. Retrieved 2015/02/19.