2-Propenoic acid, 2-nitroso-, ethyl ester

Base Information

• Chemical Name: 2-Propenoic acid, 2-nitroso-, ethyl ester
• CAS No.: 87497-88-9
• Molecular Formula: C₅H₇NO₃
• Molecular Weight: 129.115
• DSSTox Substance ID: DTXSID60448681
• Nikkaji Number: J1.837.747K
• Wikidata: Q82267783

Synonyms:2-Propenoic acid, 2-nitroso-, ethyl ester;87497-88-9;ethyl 2-nitrosoacrylate;SCHEMBL13333436;DTXSID60448681;2-Nitrosoacrylic acid ethyl ester

Chemical Property of 2-Propenoic acid, 2-nitroso-, ethyl ester

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 141

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=C)N=O

Technology Process of 2-Propenoic acid, 2-nitroso-, ethyl ester

There total 2 articles about 2-Propenoic acid, 2-nitroso-, ethyl ester 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:

ethyl 3-bromo-2-(hydroxyimino)propanoate (73472-94-3) → ethyl 2-nitrosopropenoate (87497-88-9)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(00)83872-1

Reference yield:

ethyl Bromopyruvate (70-23-5) → ethyl 2-nitrosopropenoate (87497-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NH₂OH*HCl / acetonitrile; H₂O / 6 h / 20 °C

2: iPr₂EtN / CH₂Cl₂ / 20 °C

With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; acetonitrile;

DOI:10.1515/HC.2005.11.2.173

Reference yield:

ethyl 2-nitrosopropenoate (87497-88-9) + benzalacetophenone (94-41-7) → ethyl 6-(trans,cis-2’,4’,6’-triphenyl-3’,4’-dihydro-2’H-thiopyran-3’-yl)-6-phenyl-4H-1,5,2-oxathiazine-3-carboxylate + C20H19NO3S

Guidance literature:

benzalacetophenone; With Lawessons reagent; In tetrahydrofuran; Inert atmosphere;

ethyl 2-nitrosopropenoate; In dichloromethane; at 20 ℃; for 0.583333h; regioselective reaction;

DOI:10.1002/chem.201903385

upstream raw materials:

ethyl 3-bromo-2-(hydroxyimino)propanoate

ethyl Bromopyruvate

Refernces

Synthesis of C-glycosylated amino acids by hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to exo-glycals

10.1016/j.carres.2010.12.001

The research focuses on the synthesis of C-glycosylated amino acids through the hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to exo-glycals. The main goal is to prepare C-glycoamino acids, which are stable mimics of glycosylated amino acids, potentially useful in biological studies and therapeutics. The experiments involve a series of chemical reactions, including cycloaddition, reduction, protection, and hydrogenolytic cleavage, to convert spirocyclic oxazines into C-glycosylated products. Key reactants include ethyl 2-nitrosoacrylate, exo-glycals, and various reagents for subsequent transformations. Analytical techniques used to characterize the synthesized compounds include optical rotation, NMR spectroscopy, FTIR spectroscopy, and high-resolution mass spectrometry, which confirm the structure and purity of the products obtained from each step of the synthesis.

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