Dimethyl aziridine-2,3-dicarboxylate

Base Information

• Chemical Name: Dimethyl aziridine-2,3-dicarboxylate
• CAS No.: 177473-22-2
• Molecular Formula: C₆H₉NO₄
• Molecular Weight: 159.142
• DSSTox Substance ID: DTXSID30482239
• Mol file: 177473-22-2.mol

Synonyms:dimethyl aziridine-2,3-dicarboxylate;177473-22-2;2,3-DIMETHYL AZIRIDINE-2,3-DICARBOXYLATE;SCHEMBL9328145;DTXSID30482239;EN300-88905

Chemical Property of Dimethyl aziridine-2,3-dicarboxylate

Chemical Property:

• PSA: 74.54000
• LogP: -0.99840
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 159.05315777
• Heavy Atom Count: 11
• Complexity: 171

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C(N1)C(=O)OC

Technology Process of Dimethyl aziridine-2,3-dicarboxylate

There total 10 articles about Dimethyl aziridine-2,3-dicarboxylate 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: 30.0%

(E)-dimethyl 2-diazo-3-(4-methoxybenzyloxyimino)succinate (1318796-39-2) → cis-dimethyl 5-(4-methoxyphenyl)-4,5-dihydroisoxazole-3,4-dicarboxylate + trans-dimethyl 5-(4-methoxyphenyl)-4,5-dihydroisoxazole-3,4-dicarboxylate + dimethyl aziridine-2,3-dicarboxylate (177473-22-2)

Guidance literature:

With rhodium(II) pivalate; In 1,2-dichloro-ethane; for 2h; optical yield given as %de; Inert atmosphere; Reflux;

DOI:10.1039/c1cc11683e

Reference yield: 27.0%

(E)-dimethyl 2-diazo-3-(1-phenylethoxyimino)succinate (1318796-41-6) → cis-dimethyl 5-methyl-5-phenyl-4,5-dihydroisoxazole-3,4-dicarboxylate + trans-dimethyl 5-methyl-5-phenyl-4,5-dihydroisoxazole-3,4-dicarboxylate + dimethyl aziridine-2,3-dicarboxylate (177473-22-2)

Guidance literature:

With rhodium(II) pivalate; In 1,2-dichloro-ethane; for 2h; optical yield given as %de; Inert atmosphere; Reflux;

DOI:10.1039/c1cc11683e

Reference yield: 24.0%

(E)-dimethyl 2-(benzyloxyimino)-3-diazosuccinate (1318796-37-0) → cis-dimethyl 5-phenyl-4,5-dihydroisoxazole-3,4-dicarboxylate + trans-dimethyl 5-phenyl-4,5-dihydroisoxazole-3,4-dicarboxylate + dimethyl aziridine-2,3-dicarboxylate (177473-22-2)

Guidance literature:

With rhodium(II) pivalate; In 1,2-dichloro-ethane; for 2h; optical yield given as %de; Inert atmosphere; Reflux;

DOI:10.1039/c1cc11683e

upstream raw materials:

(E)-dimethyl 2-(benzyloxyimino)-3-diazosuccinate

(E)-dimethyl 2-diazo-3-(4-methoxybenzyloxyimino)succinate

(E)-dimethyl 2-(4-chlorobenzyloxyimino)-3-diazosuccinate

(E)-dimethyl 2-diazo-3-(4-nitrobenzyloxyimino)succinate

Downstream raw materials:

dimethyl 1-acetylaziridine-2,3-dicarboxylate

trans-2,3-Dimethoxycarbonyl-aziridin