2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone
Basic information
- CAS
16691-79-5- Standard SMILES
COC(=O)C1=C(c2ccccc2)C(c2ccccc2)=C(C(=O)OC)C1=O- InChIKey
NTXFYWYVVGMAGT-UHFFFAOYSA-N- Molecular formula
- C21H16O5
- Average molar mass
- 348.3 g/mol
- Monoisotopic mass
- 348.09977361
Names & identifiers
- Preferred name
- 2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone
- IUPAC
- dimethyl 2-oxo-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylate
- English name
- 2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone
- Molecular formula
- C21H16O5
- Molecular weight
- 348.35
Names & synonyms
16691-79-52,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienoneDTXSID90385070RefChem:247135DTXCID00336093dimethyl 2-oxo-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylateMFCD001110953,5-Cyclopentadiene-1,3-dicarboxylic acid, 2-oxo-4,5-diphenyl-, dimethyl ester1,3-dimethyl 2-oxo-4,5-diphenylcyclopenta-1(5),3-diene-1,3-dicarboxylate2-oxo-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylic acid dimethyl esterNTXFYWYVVGMAGT-UHFFFAOYSA-NMaybridge3_004625
Show more names
bismethoxycarbonyldiphenylcyclopentadienoneDIMETHYL 3,4-DIPHENYLCYCLOPENTADIENONE-2,5-DICARBOXYLATE3,4-DIPHENYLCYCLOPENTADIENONE-2,5-DICARBOXYLIC ACID DIMETHYL ESTERDimethyl 3,4-Diphenylcyclopentadienone-2,5-dicarboxylate 3,4-Diphenylcyclopentadienone-2,5-dicarboxylic Acid Dimethyl Ester
Oprea1_018179SCHEMBL11720920HMS1444C05CCG-51852AKOS024323845IDI1_016012DB-043669B1962
Database identifiers
- CAS
16691-79-5- PubChem CID
- 2825971
- DTXSID
DTXSID90385070- Nikkaji
- J524.023I
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 69.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 602
Physicochemical properties
- Melting point
- 175 °C · 175 °C
- Boiling point
- 445.4 · 445.4±45.0 °C(Predicted)
- Density
- 1.302 · 1.302±0.06 g/cm3(Predicted)
- form
- powder to crystal
- color
- Light yellow to Brown
- HS Code
- 2918.3 · 2918.30.3000
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- hs_code
- 2918.30.3000
Chemistry & industry
Applications
Uses2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone is used a reagent for cycloaddition reactions.
Preparation methods
PreparationPreparative Method of 2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone: equimolar amounts of benzil and dimethyl 2-propanone-1,3-dicarboxylate in MeOH or EtOH with OH- are allowed to react at 25 °C for 1 day to give the intermediate dimethyl 3,4-diphenyl-4- hydroxycyclopent-2-enone-2,5-dicarboxylate in 70-96% yield. Treatment of the intermediate with acid in benzene or in Ac2O with heating gives the dienone in 98% yield containing 3% of the Diels-Alder dimer[1-2].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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