1,1-Cyclopentanedicarboxylic acid, 3,4-bis(methylene)-, diethyl ester

Base Information

• Chemical Name: 1,1-Cyclopentanedicarboxylic acid, 3,4-bis(methylene)-, diethyl ester
• CAS No.: 94922-11-9
• Molecular Formula: C13H18O4
• Molecular Weight: 238.28000
• DSSTox Substance ID: DTXSID20454349
• Nikkaji Number: J619.778G
• Wikidata: Q82275828
• Mol file: 94922-11-9.mol

Synonyms:1,1-Cyclopentanedicarboxylic acid, 3,4-bis(methylene)-, diethyl ester;94922-11-9;DTXSID20454349;diethyl 3,4-dimethylene-1,1-cyclopentanedicarboxylate;1,2-Dimethylenecyclopentane-4,4-dicarboxylic acid diethyl ester;3,4-dimethylene-cyclopentane-1,1-dicarboxylic acid diethyl ester

Chemical Property of 1,1-Cyclopentanedicarboxylic acid, 3,4-bis(methylene)-, diethyl ester

Chemical Property:

• PSA: 52.60000
• LogP: 2.00520
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 238.12050905
• Heavy Atom Count: 17
• Complexity: 332

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 1,1-Cyclopentanedicarboxylic acid, 3,4-bis(methylene)-, diethyl ester

There total 2 articles about 1,1-Cyclopentanedicarboxylic acid, 3,4-bis(methylene)-, diethyl 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:

diethyl 2-(2-bromo-2-propenyl)-2-(2-propenyl)propanedioate (118453-14-8) + phenylboronic acid (98-80-6) → 3,4-dimethylene-cyclopentane-1,1-dicarboxylic acid diethyl ester (94922-11-9) + 3-benzyl-4-methylene-cyclopentane-1,1-dicarboxylic acid diethyl ester

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; at 60 ℃; for 4h;

DOI:10.1021/jo025665t

Reference yield:

diethyl 2-(2-bromo-2-propenyl)-2-(2-propenyl)propanedioate (118453-14-8) → 3,4-dimethylene-cyclopentane-1,1-dicarboxylic acid diethyl ester (94922-11-9) + diethyl 5-methylenecyclohex-3-ene-1,1-dicarboxylate (94922-12-0)

Guidance literature:

With potassium carbonate; bis(triphenylphosphine) palladium (Il) acetate; In acetonitrile; at 25 ℃; for 48h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)90346-1

Reference yield: 81.0%

di(4-tosyl)amine (3695-00-9) + 3,4-dimethylene-cyclopentane-1,1-dicarboxylic acid diethyl ester (94922-11-9) → diethyl 3,4-bis((4-methyl-N-tosylphenylsulfonamido)methyl)cyclopent-3-ene-1,1-dicarboxylate (1379606-25-3)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In dichloromethane; at 20 ℃; for 18h; regioselective reaction;

DOI:10.1002/chem.201103435

upstream raw materials:

diethyl 2-(2-bromo-2-propenyl)-2-(2-propenyl)propanedioate

phenylboronic acid

Downstream raw materials:

diethyl 3-(acetoxymethyl)-4-benzylcyclopent-3-ene-1,1-dicarboxylate

diethyl 4-(acetoxymethyl)-3-(3,4-dimethylbenzyl)cyclopent-3-ene-1,1-dicarboxylate

diethyl 4-(acetoxymethyl)-3-(4-methoxybenzyl)cyclopent-3-ene-1,1-dicarboxylate

diethyl 3,4-bis((4-methyl-N-tosylphenylsulfonamido)methyl)cyclopent-3-ene-1,1-dicarboxylate