2,5-Difurfurylidenecyclopentanone; DFCPN.

• CAT Number: M334362
• CAS Number: 1026-78-4
• Molecular Formula: C15H12O3
• Molecular Weight: 240.258
• Purity: ≥95%
• Synonyms: 2,5-bis(2-furylmethylene)cyclopentanone; NSC18541.
• IUPAC Name: (2E,5E)-2,5-bis(furan-2-ylmethylidene)cyclopentan-1-one
• InChI: InChI=1S/C15H12O3/c16-15-11(9-13-3-1-7-17-13)5-6-12(15)10-14-4-2-8-18-14/h1-4,7-10H,5-6H2/b11-9+,12-10+
• InChIKey: UIVKNNAQRINTRE-WGDLNXRISA-N
• SMILES: C1CC(=CC2=CC=CO2)C(=O)C1=CC3=CC=CO3

2,5-Difurfurylidenecyclopentanone(CAS: 1026-78-4), the three five-membered rings are nearly coplanar: the dihedral angles between the cyclopentanone ring and the furan rings are 3.5 (2) and 9.7 (2)°, and the two furan rings form a dihedral angle of 7.2 (2)°. In the crystal structure, weak intermolecular C—H…O hydrogen bonds help to consolidate the crystal packing.

Reference

[1]. Ma, S-Y., and Z-B. Zheng. "(2E, 5E)-2, 5-Difurfurylidenecyclopentanone.
Acta Crystallographica Section E: Structure Reports Online 65.12 (2009): o3084-o3084.

[2]. Shibata, Mitsuhiro, and Eigo Miyazawa.
High-performance bio-based thermosetting bismaleimide resins utilizing difurfurylidenecyclopentanone and dicinnamylidene cyclopentanone.
Abstract: Difurfurylidenecyclopentanone (DFCPN) and dicinnamylidene cyclopentanone (DCCPN) were synthesized by aldol condensation reactions of cyclopentanone with furfural and cinnamaldehyde, both derived from renewable resources. The DFCPN and DCCPN were prepolymerized with 4,4′-bismaleimidodiphenylmethane (BMI) at 190 °C and then compression molded at 250 °C to produce cured DFCPN/BMI and DCCPN/BMI resins (DFCPN–BMI and DCCPN–BMI) with a molar ratio of 1/1, 1/2 or 1/3. The FT-IR spectral analysis of the cured resins and FD-MS analysis of the model reaction products using N-phenylmaleimide revealed that maleimide-rich addition copolymerization occurred. All of the cured resins except DCCPN–BMI 1/1 exhibited glass transition temperatures higher than 350 °C and 5 % weight loss temperatures higher than 450 °C, and their values increased with increasing BMI content. When cured resins with the same molar ratio were compared, DFCPN–BMI exhibited a higher flexural strength than DCCPN–BMI. Especially, DFCPN–BMI 1/1 exhibited extremely excellent flexural properties and heat resistance.
Polymer Bulletin 74.6 (2017): 1949-1963.

[3]. Tsukerman, S. V., et al.
Basicity and structure of α, Β-unsaturated heterocyclic ketones.
Abstract: The constants of the protolytic equilibrium and the displacement of the frequency of the stretching vibrations of the hydroxy group of phenol taking place under the influence of the formation of a hydrogen bond with the compounds studied have been measured for dibenzylideneacetone and dibenzylidenecycloalkanones (with five-, six-, and seven-membered rings) and their furan and selenophene analogs. It has been shown that the screening of the carbonyl group of the aliphatic ring creates considerable steric hindrance for the solvation of the carbenium ions formed in an acid medium, as the result of which the constants of the protolytic equilibrium fall on passing from compounds with an open chain to the cycloalkanone derivatives. The inclusion of a carbonyl group in a five-membered aliphatic ring creates more favorable conditions for conjugation than exist in analogous compounds with an open chain and in those with six- and seven-membered rings, in consequence of which the capacity for forming a hydrogen bond changes in the corresponding sequence.
Chemistry of Heterocyclic Compounds 4.2 (1970): 153-156.