bis(methoxycarbonyl)methylidene-imino-azanium

Base Information

• Chemical Name: bis(methoxycarbonyl)methylidene-imino-azanium
• CAS No.: 6773-29-1
• Molecular Formula: C5H6N2O4
• Molecular Weight: 158.114
• Mol file: 6773-29-1.mol

Synonyms:Malonicacid, diazo-, dimethyl ester (7CI,8CI);Propanedioic acid, diazo-, dimethylester (9CI);Bis(methoxycarbonyl)diazomethane;Diazodimethylmalonate;Diazomalonic acid dimethyl ester;Diazomalonic acid methyl ester;Diazopropanedioic acid dimethyl ester;Dicarbomethoxydiazomethane;Dimethyl2-diazomalonate;Dimethyl diazomalonate;Methyl diazomalonate;NSC 138651;

Chemical Property of bis(methoxycarbonyl)methylidene-imino-azanium

Chemical Property:

• Boiling Point: 50-52 °C(Press: 1 Torr)

Purity/Quality:

99.9% ^*data from raw suppliers

Dimethyl2-Diazomalonate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of bis(methoxycarbonyl)methylidene-imino-azanium

There total 13 articles about bis(methoxycarbonyl)methylidene-imino-azanium 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: 100.0%

malonic acid dimethyl ester (108-59-8) → dimethyl diazomalonate (6773-29-1)

Guidance literature:

With 4-acetamidobenzenesulfonyl azide; triethylamine; In acetonitrile; Inert atmosphere;

DOI:10.1021/ja309650u

Reference yield: 97.0%

4-acetamidobenzenesulfonyl azide (2158-14-7) + malonic acid dimethyl ester (108-59-8) → dimethyl diazomalonate (6773-29-1)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 17h;

DOI:10.1002/anie.201907520

Reference yield: 97.0%

4-toluenesulfonyl azide (941-55-9) + malonic acid dimethyl ester (108-59-8) → dimethyl diazomalonate (6773-29-1)

Guidance literature:

With triethylamine; In acetonitrile; at 0 - 20 ℃;

DOI:10.1021/acs.joc.6b02786

upstream raw materials:

dimethyl 2-aminomalonate

(triphenylphosphoranylidene-hydrazono)-malonic acid dimethyl ester

Dimethylmesoxalathydrazon

malonic acid dimethyl ester

Downstream raw materials:

(triphenylphosphoranylidene-hydrazono)-malonic acid dimethyl ester

dimethyl methoxymalonate

2-(4-Oxo-cyclohex-2-enyl)-malonic acid dimethyl ester

2-(2-Methyl-cyclohex-2-enyl)-malonic acid dimethyl ester

Refernces

Direct syntheses of spiro- and fused-hydrofurans by a tunable tandem semipinacol rearrangement/oxa-michael addition protocol

10.1002/chem.201300205

The research aims to develop a divergent and concise synthetic method for the construction of cycloketone spiro- and fused-dihydrofuran units, which are prevalent in biologically important natural products and potential medicinal molecules. The authors hypothesized that these units could be synthesized from a readily available diene-ketone intermediate through a tandem semipinacol rearrangement/oxa-Michael addition protocol under appropriate conditions. They successfully developed a novel one-pot tandem process for the construction of spiro- or fused-dihydrofuran products from simple furan derivatives under mild reaction conditions, using chemicals such as phenylfuranyl cyclobutanol, dimethyl diazomalonate, [Rh2(Oct)4] as a catalyst, and Lewis acids like Et2O·BF3 and THF·BF3. The method proved to be a useful and highly efficient strategy for the syntheses of differentially substituted spiro and fused compounds, with the chemoselectivity of the reaction being highly dependent on the acidity of the additives and the stability of the protecting group. The research concluded with the successful synthesis of a series of TMS-protected and TBS-protected substrates into the corresponding spiro-products and fused-products with moderate to good yields.