Morpholin-2-one

Base Information

• Chemical Name: Morpholin-2-one
• CAS No.: 4441-15-0
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.105
• Hs Code.: 2934999090
• European Community (EC) Number: 963-039-0
• DSSTox Substance ID: DTXSID10601224
• Nikkaji Number: J730.694F
• Wikidata: Q72492977
• Mol file: 4441-15-0.mol

Synonyms:Morpholin-2-one;4441-15-0;2-Morpholinone;MFCD17010143;morpholine-2-one;SCHEMBL371880;DTXSID10601224;ZQHJAAMMKABEBS-UHFFFAOYSA-N;BCP31643;RB3226;AKOS006346826;AB71646;AM62713;AS-54431;DA-05797;SY047308;CS-0098127;A934324

Chemical Property of Morpholin-2-one

Chemical Property:

• Vapor Pressure: 0.014mmHg at 25°C
• Melting Point: 178℃
• Boiling Point: 258.561oC at 760 mmHg
• PKA: 6.89±0.20(Predicted)
• Flash Point: 110.174oC
• PSA: 38.33000
• Density: 1.123g/cm3
• LogP: -0.53840
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 101.047678466
• Heavy Atom Count: 7
• Complexity: 81.8

Purity/Quality:

98%, ^*data from raw suppliers

Morpholin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC(=O)CN1
• General Description: Morpholin-2-one is a heterocyclic compound that can be synthesized via Stevens [1,2]-shift reactions of cyclic ammonium ylides, particularly from 2-(N,N-dialkylamino)ethyl diazoacetoacetates under copper catalysis. The reaction proceeds efficiently with benzylic or allylic migrating groups, yielding morpholinones in moderate to good yields, while simple alkyl groups (except tert-butyl) are less effective. This method offers a practical route to morpholin-2-ones, which are valuable intermediates for the synthesis of amino acid derivatives.

Technology Process of Morpholin-2-one

There total 11 articles about Morpholin-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: 94.0%

2-morpholinone hydrochloride → morpholin-2-one (4441-15-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h; Reagent/catalyst;

Reference yield: 88.0%

chloroacetic acid ethyl ester (105-39-5) → morpholin-2-one (4441-15-0)

Guidance literature:

With (1R,2S)-1-Amino-2-indanol; sodium hydride; In tetrahydrofuran; mineral oil; at 20 - 70 ℃; for 1.58333h; Inert atmosphere; Reflux;

Reference yield: 76.0%

4-benzyl-morpholin-2-one (5453-99-6) → morpholin-2-one (4441-15-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 12h; under 3102.97 Torr;

DOI:10.1016/j.bmcl.2014.09.056

upstream raw materials:

N-(2-hydroxyethyl)iminodiacetic acid

oxirane

glycine

GlyOEt*HCl

Downstream raw materials:

5a(S),10b(R)-5a,10b-dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate

4-(2-hydroxyethyl)-2-piperazinone

2-oxo-4-morpholinecarboxylic acidtert-butyl ester

4-[4-(Dibenzylamino)-3-fluorophenyl]morpholin-3-one

Refernces

Applications of Stevens [1,2]-shifts of cyclic ammonium ylides. A route to morpholin-2-ones

10.1021/jo00099a041

The study explores the synthesis of morpholin-2-ones via the Stevens [1,2]-shift mechanism. The researchers prepared 2-(N,N-dialkylamino)ethyl diazoacetoacetates (compounds 2) from readily available ethanolamines (compounds 1) in a two-step process. These diazoacetoacetates were then heated in the presence of catalytic copper to form morpholinones (compounds 3), presumably via the intermediacy of copper carbenoids and cyclic ammonium ylides. The study found that benzylic or allylic migrating groups typically underwent the [1,2]-shift in good yield (55-80%), while simple alkyl groups, except for tert-butyl, failed to rearrange. The study also investigated the use of different copper catalysts and their impact on the yield of the desired morpholinone products. The findings suggest that this method provides a straightforward route to morpholinones, which can serve as precursors to various amino acid derivatives, thus contributing to the development of synthetic methods for a-amino acids and their derivatives.

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