42019-88-5

Usage

Uses

Used in Pharmaceutical Industry:
2,5-BIS[(4-CHLOROPHENYL)METHYLENE]CYCLOPENTANONE is used as a synthetic intermediate for the production of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Dye Industry:
In the dye industry, 2,5-BIS[(4-CHLOROPHENYL)METHYLENE]CYCLOPENTANONE is utilized as an intermediate in the synthesis of dyes, playing a crucial role in the creation of colorants for various applications.
Used in Organic Synthesis:
2,5-BIS[(4-CHLOROPHENYL)METHYLENE]CYCLOPENTANONE is used as a starting material in organic synthesis, particularly for the formation of heterocyclic compounds, which are important in the development of complex organic molecules.
Used in Organic Chemistry Research:
As a reagent in organic chemistry research, 2,5-BIS[(4-CHLOROPHENYL)METHYLENE]CYCLOPENTANONE aids in conducting experiments and advancing the understanding of chemical reactions and mechanisms.
Used in Specialty Chemicals Production:
In the production of specialty chemicals, 2,5-BIS[(4-CHLOROPHENYL)METHYLENE]CYCLOPENTANONE is employed as a key component, contributing to the manufacturing of unique and high-value chemical products.

InChI:InChI=1/C19H14Cl2O/c20-17-7-1-13(2-8-17)11-15-5-6-16(19(15)22)12-14-3-9-18(21)10-4-14/h1-4,7-12H,5-6H2

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 120-92-3 cyclopentanone 
• 23786-93-8 1,1-diethoxy-cyclopentane 
• 580-15-4 6-aminoquinoline 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 

Downstream Products

• 1261032-46-5 1-N-methyl-spiro[2.3']oxindole-spiro[3.2]5-(4-chloro)benzylidenecyclopentanone-4-(4-chloro)phenyl-pyrrolidine 
• 1392494-90-4 7'-(4-chlorobenzylidene)-4'-(4-chlorophenyl)-4',5',6',7'-tetrahydro-2'H-spiro[cyclopentane-1,3'-cyclopenta[b]pyran]-2'-one 
• 1392494-95-9 7'-(4-chlorobenzylidene)-4'-(4-chlorophenyl)-4',5',6',7'-tetrahydro-2'H-spiro[cyclohexane-1,3'-cyclopenta[b]pyran]-2'-one 
• 1427056-50-5 3-(4-chlorobenzylidene)-9-(4-chlorophenyl)-6,6-dimethyl-2,3,6,7-tetrahydrocyclopenta[b]chromen-8(1H,5H,9H)-one 
• 115591-90-7 1,3-Bis<(E)-(4-chlorphenyl)methylen>-2-(phenylmethylen)cyclopentan 
• 1566611-32-2 1,2-bis(4-(4-chlorophenyl)-1H-pyrrol-3-yl)ethane 
• 1217079-04-3 ethyl (E)-7-(4-chlorobenzylidene)-4-(4-chlorophenyl)-6-oxospiro[4.4]non-1-ene-1-carboxylate 

Relevant academic research and scientific papers

Green, rapid, and highly efficient syntheses of α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen–Schmidt condensation catalyzed by MoCl5

A new, green, and highly efficient protocol for the expeditious preparation of some α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones via a simple microwave-assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent-free conditions, simple operation, use of a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.

Diarylidenecyclopentanone derivatives as potent anti-inflammatory and anticancer agents

Cancer is often associated with chronic inflammation. In order to develop potential anticancer and anti-inflammatory agents a series of 26 diarylidenecyclopentanones (DACPs) Ia–Iv, II, III, and IV were synthesized. Five of the synthesized DACPs are novel (Ih, Ij, Ik, Is, and Iv), derivative Iv was characterized using single-crystal X-ray diffraction study. All the synthesized derivatives were tested for their anti-inflammatory as well as cytotoxicity properties. Compound Is is found to have the highest anti-inflammatory activity (93.67%) by inhibiting PGE2 (prostaglandin E2) production. Three of the DACPs (Io, It, and Iu) were observed to have high cytotoxicity with IC50 value of 8.73 ± 0.06 μM (Io), 12.55 ± 0.31 μM (It), and 11.47 ± 0.15 μM (Iu) against HeLa cells. Further staining and cell cycle analysis was done using these three DACPs to understand their mechanism of action. The G0/G1 phase was observed to be the longest one through which the cells undergo apoptosis.

Antiparasitic activity of synthetic curcumin monocarbonyl analogues against Trichomonas vaginalis

Trichomoniasis is a parasitic infection caused by Trichomonas vaginalis and it is considered to be the most common non-viral sexually transmitted infection in the world. Since the 1960s, nitroimidazoles such as metronidazole are the drugs of choice for the treatment of trichomoniasis, but many adverse effects and allergic reactions may result from their use. Reports of metronidazole-resistant infections also highlight the importance for the search of new anti-T. vaginalis agents. Considering this, herein we report the anti-T. vaginalis evaluation of 21 synthetic monocarbonyl analogues of curcumin, which itself has been reported to possess antiparasitic potential. From the in vitro analysis of the synthetic molecules, untreated trophozoites, and metronidazole at 100 μM, it was observed that three curcumin analogues (3a, 3e, and 5e) exhibited anti-T. vaginalis activity comparable to metronidazole (no significant statistical difference). Optimal antiparasitic concentrations were determined to be 80 μM and 90 μM for propanone derivatives 3a and 3e, respectively, and 200 μM for cyclohexanone derivative 5e. Kinetic growth curves showed that, after 24 h, the trophozoites were completely inhibited. At the tested concentrations, natural curcumin did not significantly inhibit the growth of trophozoites, therefore demonstrating that the designed synthetic molecules not only have better chemical stability, but also higher anti-T. vaginalis potential. Cytotoxicity analysis, performed on VERO cells, demonstrated low, moderate and high cytotoxic effects for analogues 3e, 5e and 3a, respectively. This study suggests that these analogues possess chemical features of interest to be further explored as alternatives for the treatment of trichomoniasis.

Sulfonated PEG-intercalated montmorillonite [(Mt/PEG)-SO3H] as efficient and ecofriendly nanocatalyst for synthesis of α,α′-bis(substituted benzylidene)cycloalkanones

(Montmorillonite/PEG)-SO3H nanocomposite was successfully prepared for the first time and introduced as a solid acid nanocatalyst. Initially, polyethylene glycol (PEG) polymeric chains were intercalated into interlayer spaces of montmorillonite. The resulting Mt/PEG nanocomposite with good mechanical and thermal stability was chosen as a useful clay mineral/polymer support for further modification with chlorosulfonic acid. Structural characterization of (Mt/PEG)-SO3H was carried out using X-ray diffraction (XRD) analysis, Brunauer–Emmett–Teller (BET) measurements, Barrett–Joyner–Halenda (BJH) analysis, scanning electron microscopy (SEM), thermogravimetric analysis (TGA), and Fourier-transform infrared (FT-IR) spectroscopy. The results showed that PEG chains were intercalated into the clay mineral layers and that the Mt/PEG nanocomposite was successfully sulfonated. (Mt/PEG)-SO3H nanocomposite exhibited high specific surface area and good stability up to around 150?°C, showing excellent potential for application as a recyclable nanocatalyst. (Mt/PEG)-SO3H was used as an efficient and ecofriendly solid acid nanocatalyst for preparation of α,α′-bis(substituted benzylidene)cycloalkanones under solvent-free conditions, leading to many interesting findings. The excellent conversion values confirm that the catalyst has strong and sufficient acidic sites, which are responsible for its catalytic performance. The reaction under mild conditions (room temperature) with excellent yield, catalyst recyclability (up to ten times), and simple work-up procedure represent useful advantages of (Mt/PEG)-SO3H for catalysis. Moreover, the reaction could be scaled up to 10 and 15?mmol scales.

An efficient green approach to aldol and cross-aldol condensations of ketones with aromatic aldehydes catalyzed by nanometasilica disulfuric acid in water

Aldol and cross-aldol condensations of aromatic aldehydes with various ketones in the presence of nanometasilica disulfuric acid (NMSDSA) as heterogeneous catalyst are presented. The catalyst was prepared according to the developed earlier method using inexpensive and readily available starting materials. The highly active catalyst gave excellent yields of the desired aldol products without self-condensation reaction taking place. Reaction times were short, the procedure and work-up were simple, and no volatile or hazardous organic solvents were involved. The catalyst could be recovered three times with only slight reduction in activity.

Synthesis, characterization, and crystal structures of α, α'-bis(substituted-benzylidene)cycloalkanone derivatives by nano-TiO2/HOAc

A new and economical synthesis of α, α'-bis(substituted-benzylidene)cycloalkanones has been achieved by the reaction of cycloalkanones with different aromatic aldehydes using nano-TiO2/acetic acid as a catalyst in ethanol under reflux conditions with excellent yields. Five new products and three new single crystal structures are reported.

Nano titania-supported sulfonic acid catalyzed synthesis of α,α'-bis(substituted-benzylidene)cycloalkanones and of their xanthene derivatives under solvent-free conditions

An efficient, rapid and green synthesis of α,α'-bis(substituted-benzylidene)cycloalkanones and their xanthene derivatives is reported under solvent-free conditions using nano titania-supported sulfonic acid (n-TSA) as a reusable catalyst. This method offers many advantages, such as environmental friendliness reaction conditions, simplicity, short reaction times, easy work-up, reusability of catalyst, and high yields of products. Eight new compounds are reported too.

Nanomagnetic-supported Sulfonic Acid: Simple and Rapid Method for the Synthesis of α,α′-Bis-(substituted-benzylidene) Cycloalkanones

Nanomagnetic-supported sulfonic acid is found to be a powerful and reusable heterogeneous catalyst for the rapid synthesis of α,α′-bis-(substituted-benzylidene)cycloalkanones under conventional heating and solvent free conditions. High yield, simple work up and easy recovery of the catalyst are the most obvious advantages of this procedure. In this paper, an efficient, sustainable and green procedure for synthesis of α,′α-bis-(substituted-benzylidene) cycloalkanones has been developed using a magnetically separable and easily recyclable nano-γ-Fe2O3-SO3H catalyst in solvent free medium under thermal condition. Easy magnetic separation of the catalyst eliminates the requirement of catalyst filtration after completion of the reaction which is an additional greener attribute of this method.

Efficient method for the synthesis of, ′-bis(arylmethylidene) cycloalkanones catalyzed by bromodimethylsulfonium bromide

Bromodimethylsulfonium bromide (BDMS)-catalyzed crossed aldol condensation between aromatic aldehydes and ketones is reported to access ′-bis(arylmethylidene) cycloalkanones at room temperature in good yields within 3-10 min. The salient features of this method are the simplicity of the procedure, the ready accessibility of the catalyst, and greater yields in relatively short reaction times. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Solvent-free catalytic preparation of 2,6-dibenzylidenecycloalkanones using 2-hydroxyethylammonium acetate ionic liquid as catalyst

Various 2,6-dibenzylidenecycloalkanones were readily prepared in a condensation reaction catalyzed by 2-hydroxyethylammonium acetate ionic liquid under solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times, lack of solvent, simplicity of performance, and low cost. Graphical abstract: [Figure not available: see fulltext.]