Diethyl 2-phenylcyclopropane-1,1-dicarboxylate

Base Information

• Chemical Name: Diethyl 2-phenylcyclopropane-1,1-dicarboxylate
• CAS No.: 3092-20-4
• Molecular Formula: C15H18 O4
• Molecular Weight: 262.306
• European Community (EC) Number: 654-108-3
• NSC Number: 88160
• DSSTox Substance ID: DTXSID30293266
• Nikkaji Number: J699.823B
• ChEMBL ID: CHEMBL1421551
• Mol file: 3092-20-4.mol

Synonyms:3092-20-4;diethyl 2-phenylcyclopropane-1,1-dicarboxylate;diethyl 2-phenyl-1,1-cyclopropanedicarboxylate;MLS000326954;1,1-diethyl 2-phenylcyclopropane-1,1-dicarboxylate;SMR000179481;1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, 1,1-diethyl ester;NSC88160;Glucosamine derivative, 5;Oprea1_001168;cid_258820;CHEMBL1421551;BDBM43832;DTXSID30293266;HMS2286D15;NSC-88160;AKOS005075776;CS-0361268;diethyl2-phenylcyclopropane-1,1-dicarboxylate;10P-038;2-phenylcyclopropane-1,1-dicarboxylic acid diethyl ester;2-phenyl-cyclopropane-1,1-dicarboxylic acid diethyl ester

Chemical Property of Diethyl 2-phenylcyclopropane-1,1-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.000252mmHg at 25°C
• Boiling Point: 324.1°C at 760 mmHg
• Flash Point: 153°C
• PSA: 52.60000
• Density: 1.17g/cm³
• LogP: 2.28650
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 262.12050905
• Heavy Atom Count: 19
• Complexity: 326

Purity/Quality:

99%min ^*data from raw suppliers

DIETHYL 2-PHENYLCYCLOPROPANE-1,1-DICARBOXYLATE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CC1C2=CC=CC=C2)C(=O)OCC

Technology Process of Diethyl 2-phenylcyclopropane-1,1-dicarboxylate

There total 17 articles about Diethyl 2-phenylcyclopropane-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: 98.0%

trimethylsulfoxonium iodide (1774-47-6) + diethyl benzalmalonate (5292-53-5) → diethyl 2-phenylcyclopropane-1,1-dicarboxylate (3092-20-4)

Guidance literature:

With hydrogen; sodium hydride; In dimethyl sulfoxide; at 0 - 20 ℃;

DOI:10.1016/j.ejmech.2014.12.032

Reference yield: 88.8%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 1,3-diethyl 2-diazopropanedioate (5256-74-6) → diethyl 2-phenylcyclopropane-1,1-dicarboxylate (3092-20-4)

Guidance literature:

copper; In 1,2-dichloro-ethane; at 180 ℃; Product distribution / selectivity;

Reference yield: 80.0%

diethyl benzalmalonate (5292-53-5) + dimethylsulfoxonium methylide (70775-39-2,5367-24-8) → diethyl 2-phenylcyclopropane-1,1-dicarboxylate (3092-20-4)

Guidance literature:

In tetrahydrofuran; mineral oil; at 20 - 50 ℃; for 4.5h; Inert atmosphere;

upstream raw materials:

Methyl-phenyl-sulfonium-diethoxyphosphinyl-methylid

benzaldehyde

diethyl malonate

styrene

Downstream raw materials:

2'-phenylpyrimidine-5-spirocyclopropane-2,4,6(1H,3H,5H)-trione

{2-[(Z)-1,2-diphenylvinyl]phenyl}(phenyl)methanone

1-(ethoxycarbonyl)-2-phenylcyclopropanecarboxylic acid

Refernces

• 1、 Kawabata, Nariyoshi,Yanao, Shinji,Yoshida, Jun-ichi. "Copper(II) Halide Catalyzed Cyclopropanation of Olefins Involving Dehydrobromination of Bromomalonic Ester by Amine". . p. 2687 - 2688. Retrieved 1982.
• 2、 Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh. "Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine". supporting information. p. 6535 - 6550. Retrieved 2020/06/09.
• 3、 Mishra, Manmath,De, Pinaki Bhusan,Pradhan, Sourav,Punniyamurthy, Tharmalingam. "Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines". . p. 10901 - 10910. Retrieved 2019/09/13.