893-00-5

Usage

Chemical Family

Furan derivatives

Physical State

Yellowish liquid

Odor

Strong, sweet

Usage

Flavoring agent in the food industry

Synthesis

Used in the production of pharmaceuticals and agrochemicals

Medical Applications

Potential anti-inflammatory and anti-cancer properties

Safety

Potentially hazardous if not properly controlled and handled

InChI:InChI=1/C16H14O3/c17-16-12(10-14-6-2-8-18-14)4-1-5-13(16)11-15-7-3-9-19-15/h2-3,6-11H,1,4-5H2

Upstream product

• 15022-16-9 2-(furan-2-yl)acetaldehyde 
• 108-94-1 cyclohexanone 
• 98-01-1 furfural 

Relevant academic research and scientific papers

Synthesis of furan derivative as LED light photoinitiator: One-pot, low usage, photobleaching for light color 3D printing

A type II photoinitiator, containing furan structure, 2,6-bis(furan-2-ylmethylidene) cyclohexan-1-one (BFC) was synthesized via one step reaction between furan and cyclohexanone. This photoinitiator has large molar extinction coefficient and long wavelength absorption attributing to its large conjugation structure. Photopolymerization kinetics reveals that photoinitiator BFC at low concentration exhibits the high polymerization rate and conversion. UV-vis absorption and fluorescence spectrum demonstrate that BFC has a big red shift in the polyethylene glycoldiacrylate (PEGDA) solution and the light absorption region could be extended to 500 nm because of exciplex formed by BFC and PEGDA. Moreover, PEGDA is the excellent hydrogen donor to photoinitiator BFC compared with traditional coinitator amine. This BFC/PEGDA photoinitiator system has an outstanding photobleaching performance, which has potential to be used in the light-color materials with visible light photopolymerization, such as 3D photopolymerization printing material with long wavelength LED lamp.

Production of renewable long-chained cycloalkanes from biomass-derived furfurals and cyclic ketones

Developing renewable long-chain cycloalkanes from lignocellulosic biomass is of significance because it offers huge resource storage, wide applications in aviation/diesel fuels and mitigation of CO2 emissions. In this paper, cycloalkanes with carbon chain lengths of 13-18 were produced from biomass-derived furfural species (furfural and 5-hydroxymethylfurfural) and cyclic ketones (cyclopentanone and cyclohexanone) via aldol condensation, followed by hydrogenation to saturate the CC and CO bonds, and hydrodeoxygenation to remove oxygen atoms. The aldol condensation of the furfural species with cyclic ketones was catalyzed by NaOH and the target condensation intermediates were obtained in yields of more than 90% at room temperature (30 °C) with a short reaction time (40 min). By using amorphous zirconium phosphate combined with Pd/C as the catalyst, liquid cycloalkanes were produced at the optimal conditions with a yield of 76%. When the combined solid catalyst was reused, the target products reduced after the second run but the initial yield could be largely recovered by recalcination of the spent zirconium phosphate. Considering that cyclopentanone and cyclohexanone can be easily produced from furfural (originating from hemicellulose) and phenol (originating from lignin), respectively, this condensation has the potential to achieve the integrated conversion of biomass-derived cellulose, hemicellulose and lignin to jet fuel and/or diesel additives.

Synthesis of diarylidenecyclohexanone derivatives as potential anti-inflammatory leads against COX-2/mPGES1 and 5-LOX

Inflammation is a pathophysiological condition which progresses through the prostaglandin (PG) and leukotriene (LT) pathways channelized by the enzymes COX/mPGES1 and 5-LOX respectively. Diarylidenecyclohexanone (DAC) derivatives (Ia-j, IIa-c, IIIa and IVa) were synthesized, characterized and screened for their in vitro anti-inflammatory activity via inhibition of 5-LOX and COX-2/mPGES1 enzymes. Compound Ic inhibited PGE2 production exhibiting an IC50 of 6.7 ± 0.19 μM, comparable to the standard inhibitor, licofelone (IC50 of 5.4 ± 0.02 μM). Compounds Ie and Ig showed maximum in vitro inhibitory activity against 5-LOX, exhibiting an IC50 of 1.4 ± 0.1 μM and 1.5 ± 0.13 μM, respectively, and these are comparable to that of the standard drug, zileuton (IC50 = 1.2 ± 0.11 μM). Ie and Ig do not possess radical scavenging properties and may not be disrupting the redox cycle of the enzyme. Hence they may be inhibiting the enzyme by a competitive mode. One of the compounds in the DAC series (IIc) containing a heterocyclic thienyl ring inhibited all the three enzymes. It inhibited 5-LOX and COX-2/mPGES1 with an IC50 of 1.8 ± 0.12 μM and 7.5 ± 0.4 μM respectively. An RT-PCR based mRNA expression study highlighted that Ic predominantly inhibited the expression of COX-2 rather than mPGES1. No toxicity towards the HeLa cell line indicated that the DACs could serve as structural templates towards lead optimization of compounds for discovery of novel, potent, safe and affordable drugs as anti-inflammatory agents.

Synthesis, mechanistic and synergy studies of diarylidenecyclohexanone derivatives as new antiplasmodial pharmacophores

Diarylidenecyclohexanone (DAC) derivatives (Ia-i, IIa-c and IIIa-b) were synthesized, characterized and screened for their invitro antiplasmodial activities against erythrocytic stages of chloroquine (CQ) sensitive and resistant strains of P. falciparum by using SYBR green I fluorescence assay. SAR studies of DAC derivatives showed antiplasmodial activity in the order of 3-NO2 (Ib, IC50 0.95 μM) > 3-chloro (Id, IC50 3 μM) > 4-chloro (Ie, IC50 8.5 μM) > 2-chloro (Ic, IC50 13 μM). Further Ib and Id exhibited nearly equal potencies against CQ-resistant strains P. falciparum Dd2, {IC50 1 μM (Ib) and 2.7 μM (Id)} and PfINDO {IC50 1.1 μM (Ib) and 2.5 μM (Id)}. Drug exposure followed by drug withdrawal-based stage-specific kill kinetic studies showed that Ib is shizonticidal within 3 h while the earliest killing actions against Trophozoites and Rings were seen at >3 h and >6 h, respectively. Combination studies of the most potent leads viz. Ib and Id showed strong to moderate synergistic effects with Artemisinin (?FIC50: 0.34 to 0.63) whereas no interaction (?FIC50: 0.65 to 2.36) was observed with Chloroquine. The DACs showed significant insilico binding affinity with β-haematin and P. falciparum lactate dehydrogenase (PfLDH) suggesting these to be the targets of their antiplasmodial action. High compliance with Lipinski rule of 5 and high selectivity index of Ib (105.3) and Id (8.3) against HeLa cell line indicated that Diarylidenecyclohexanones could serve as structural templates towards lead optimization of compounds for discovery of novel, potent, safe and affordable drugs against malaria.

Preparation method for synthesizing photosensitive compound through Claisen-Schmidt reaction

The invention provides a preparation method for synthesizing a photosensitive compound through a Claisen-Schmidt reaction. An aldehyde free of alpha-H and a ketone containing alpha-H are selected to be synthesized to obtain the product alpha, beta-unsaturated aldehyde ketone. The preparation method is simple in condition and mild in reaction. The prepared photosensitive compound serving as a hydrogen abstraction type photoinitiator is long in wave length and small in consumption, and has a good initiation effect on monomer PEFDA without adding initiation auxiliaries. Under an ultraviolet lamp,the absorption wavelength is subjected to red shift from 450 to 500 and finally subjected to blue shift to 400 or below. The photosensitive compound has an AIE effect.

Using Mg-Al Mixed Oxide and Reconstructed Hydrotalcite as Basic Catalysts for Aldol Condensation of Furfural and Cyclohexanone

This study presents results on aldol condensation of furfural and cyclohexanone in presence of Mg-Al hydrotalcite-derived materials as solid basic catalysts at reaction temperatures from 25 to 90 °C and a cyclohexanone to furfural molar ratio of 1–10. Mg-Al mixed oxide exhibited reasonable activity with furfural conversion of ca. 50 % after 180 min of the reaction at T=90 °C. The activity of reconstructed hydrotalcite was much higher with furfural conversion close to 100 % at short reaction times. In comparison with Mg-Al mixed oxide, the initial reaction rate has increased 30–50 times. Under similar reaction conditions, cyclohexanone self-condensation on HTC-derived catalysts could not compete with aldol condensation because the former reaction was inhibited by produced water. The change in CH/F molar ratio influenced both furfural conversion and product selectivity; higher furfural content in the reaction mixture favored the second condensation step.

Continuous Microflow Synthesis of Fuel Precursors from Platform Molecules Catalyzed by 1,5,7-Triazabicyclo[4.4.0]dec-5-ene

The first continuous flow synthesis of C8-C16 alkane fuel precursors from biobased platform molecules is reported. TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) was found to be a recyclable and highly efficient organic base catalyst for the aldol condensation of furfural with carbonyl compounds, and the selectivity of mono- or difuryl product can be easily regulated by adjusting the molar ratio of substrates. By means of flow technique, a shorter reaction time, satisfactory output, and continuous preparation are achieved under the present procedure, representing a significant advance over the corresponding batch reaction conditions.

Sulfuric acid-modified PEG-6000 (PEG-SO3H): An efficient, bio-degradable and reusable catalyst for synthesis of α, α′ bis(arylidene) cycloalkanones under solvent-free conditions

A green and efficient method for synthesis of α, α′ -bis (arylidene) cycloalkanones, starting from aromatic aldehydes in reaction with ketones using sulfonated polyethylene glycol 6000 (PEG-SO3H) as a stable, reusable and biodegradable catalyst under solvent-free conditions at 80 °C is described. The use of a nontoxic, inexpensive, easily available and recyclable catalyst makes this protocol practical, environmentally friendly and economically attractive.

Study of in situ generation of carbocationic system from trityl chloride (Ph3CCl) which efficiently catalyzed cross-aldol condensation reaction

Organocatalyst trityl chloride (Ph3CCl), by in situ formation of trityl carbocation with inherent instability, efficiently promotes the cross-aldol condensation reaction between cycloalkanones and arylaldehydes in solvent-free and homogeneous media to afford α,α′- bis(arylidene)cycloalkanones in high yields. Moreover, an attractive and plausible mechanism based on observations and the literature is proposed for the reaction.

Amberlyst-15 catalysed microwave assisted cross-aldol condensation between ketones and aldehydes under solvent free condition

Amberlyst-15 has been applied as an efficient heterogeneous catalyst for the first time for rapid synthesis of α,α′-bis(arylmethylene) cycloalkanones, α,α′-bis(cinnamylidene)cycloalkanones, ′-cinnamylideneacetophenones and chalcones in very good yield by the reaction between various aldehydes and ketones under microwave irradiation. The new process for the cross-aldol condensation reaction works well in absence of any solvent. The yields are high and the process is environmentally benign.