Dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate

Base Information

• Chemical Name: Dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate
• CAS No.: 61373-18-0
• Molecular Formula: C₁₃H₁₃NO₆
• Molecular Weight: 279.249
• DSSTox Substance ID: DTXSID60587367
• Nikkaji Number: J3.647.658C
• Mol file: 61373-18-0.mol

Synonyms:61373-18-0;Dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate;DTXSID60587367;dimethyl 2-(4-nitrophenyl)cyclopropane-1,1dicarboxylate

Chemical Property of Dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 279.07428713
• Heavy Atom Count: 20
• Complexity: 405

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CC1C2=CC=C(C=C2)[N+](=O)[O-])C(=O)OC

Technology Process of Dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate

There total 8 articles about Dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-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: 43.0%

4-nitrostyrene (100-13-0) + dimethyl diazomalonate (6773-29-1) → dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate (127604-91-5,61373-18-0)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1021/acs.orglett.7b03961

Reference yield:

4-nitrobenzaldehdye (555-16-8) → dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate (127604-91-5,61373-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine; acetic acid / benzene / 3 h / Reflux

2: sodium hydride / dimethyl sulfoxide / 20 °C / Inert atmosphere

With piperidine; sodium hydride; acetic acid; In dimethyl sulfoxide; benzene;

DOI:10.1021/jo300720d

Reference yield:

malonic acid dimethyl ester (108-59-8) → dimethyl 2-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate (127604-91-5,61373-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine; acetic acid / benzene / 3 h / Reflux

2: sodium hydride / dimethyl sulfoxide / 20 °C / Inert atmosphere

With piperidine; sodium hydride; acetic acid; In dimethyl sulfoxide; benzene;

DOI:10.1021/jo300720d

upstream raw materials:

dimethyl (4-nitrobenzylidene)malonate

4-nitrostyrene

bis(methoxycarbonyl)(phenyliodinio)methanide

trimethylsulfoxonium iodide