3-oxo-1H-indene-2,2-dicarboxylic acid diethyl ester

Base Information

• Chemical Name: 3-oxo-1H-indene-2,2-dicarboxylic acid diethyl ester
• CAS No.: 122951-09-1
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.289
• DSSTox Substance ID: DTXSID401197777
• Nikkaji Number: J915.790E
• Mol file: 122951-09-1.mol

Synonyms:DTXSID401197777;122951-09-1;3-oxo-1H-indene-2,2-dicarboxylic acid diethyl ester;diethyl 1-oxo-1,3-dihydro-2H-indene-2,2-dicarboxylate;2,2-Diethyl 1,3-dihydro-1-oxo-2H-indene-2,2-dicarboxylate

Chemical Property of 3-oxo-1H-indene-2,2-dicarboxylic acid diethyl ester

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 276.09977361
• Heavy Atom Count: 20
• Complexity: 397

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1(CC2=CC=CC=C2C1=O)C(=O)OCC

Technology Process of 3-oxo-1H-indene-2,2-dicarboxylic acid diethyl ester

There total 2 articles about 3-oxo-1H-indene-2,2-dicarboxylic acid 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: 76.0%

diethyl (2-iodobenzyl)malonate (111373-31-0) + phenyl formate (1864-94-4) → diethyl 2-(2-(phenoxycarbonyl)benzyl)malonate + 1,3-dihydro-1-oxo-2H-indene-2,2-dicarboxylic acid diethyl ester (122951-09-1)

Guidance literature:

With triethylamine; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In dimethyl sulfoxide; at 80 ℃; for 5h; Reagent/catalyst; Solvent; Time; Inert atmosphere;

DOI:10.1039/c4cc09413a

Reference yield:

diethyl 2-(2-bromobenzyl)propan-1,3-dioate (66192-11-8) + β-naphthaldehyde (66-99-9) → naphthalene (91-20-3,71998-51-1,72931-45-4) + 1,3-dihydro-1-oxo-2H-indene-2,2-dicarboxylic acid diethyl ester (122951-09-1)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,3-bis-(diphenylphosphino)propane; Pd(1,3-bis(diphenylphosphino)propane)₂; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; at 130 ℃; for 6h; Overall yield = 80 percent; Inert atmosphere;

DOI:10.1002/asia.201901595

upstream raw materials:

diethyl (2-iodobenzyl)malonate

phenyl formate

diethyl 2-(2-bromobenzyl)propan-1,3-dioate

β-naphthaldehyde