1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester

Base Information

• Chemical Name: 1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester
• CAS No.: 3709-20-4
• Molecular Formula: C13H14O4
• Molecular Weight: 234.252
• DSSTox Substance ID: DTXSID20458382
• Nikkaji Number: J671.679B
• Mol file: 3709-20-4.mol

Synonyms:Dimethyl 2-phenylcyclopropane-1,1-dicarboxylate;3709-20-4;1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester;SCHEMBL5961926;DTXSID20458382;HEDVHUQQVZUKBN-UHFFFAOYSA-N;MFCD34182086;SB21971;WS-00983;E72540;1,1-Dimethyl 2-phenylcyclopropane-1,1-dicarboxylate;2-Phenyl-1,1-cyclopropanedicarboxylic acid dimethyl ester;1,1-DIMETHYL (2S)-2-PHENYLCYCLOPROPANE-1,1-DICARBOXYLATE

Chemical Property of 1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 234.08920892
• Heavy Atom Count: 17
• Complexity: 301

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1(CC1C2=CC=CC=C2)C(=O)OC

Technology Process of 1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl ester

There total 42 articles about 1,1-Cyclopropanedicarboxylic acid, 2-phenyl-, dimethyl 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: 97.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + dimethyl diazomalonate (6773-29-1) → dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate (3709-20-4)

Guidance literature:

styrene; With bis[rhodium(α,α,α',α'-tetramethyl-1,3-benzenedipropionic acid)]; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

dimethyl diazomalonate; In dichloromethane; at 0 - 23 ℃; Inert atmosphere;

DOI:10.1002/chem.201102583

Reference yield: 95.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + bis(methoxycarbonyl)(phenyliodinio)methanide (145838-86-4) → dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate (3709-20-4)

Guidance literature:

With bis[rhodium(α,α,α',α'-tetramethyl-1,3-benzenedipropionic acid)]; In dichloromethane; at 2 - 20 ℃; Inert atmosphere;

DOI:10.1002/0471264229.os087.13

Reference yield: 91.0%

dimethyl (2S)-2-phenylcyclopropane-1,1-dicarboxylate (158800-60-3) → dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate (3709-20-4)

Guidance literature:

With Co(meso-tetraphenylporphyrin) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; In 1,2-dichloro-ethane; at 55 ℃; for 4h; Inert atmosphere; Sealed tube;

DOI:10.1055/s-0034-1378394

upstream raw materials:

diazomethane

2-phenyl-1,1-cyclopropanedicarboxylic acid

1-methoxycarbonyl-2-phenylcyclopropanecarboxylic acid

styrene

Refernces

• 1、 Nishiyama, Hisao,Aoki, Katsuyuki,Itoh, Hirofumi,Iwamura, Taichiro,Sakata, Naoya,Kurihara, Osamu,Motoyama, Yukihiro. "Stable dicarbonylcarbene complexes of bis(oxazolinyl)pyridine ruthenium and osmium". . p. 1071 - 1072. Retrieved 1996.
• 2、 Borisov, Denis D.,Chermashentsev, Grigorii R.,Novikov, Roman A.,Tomilov, Yury V.. "Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates". . p. 2253 - 2259. Retrieved 2021/03/04.
• 3、 Jacob, Anu,Jones, Peter G.,Werz, Daniel B.. "(3 + 2)-Cycloaddition of Donor-Acceptor Cyclopropanes with Selenocyanate: Synthesis of Dihydroselenophenes and Selenophenes". supporting information. . Retrieved 2020/11/13.