42019-85-2

Usage

Appearance

Yellow to brown crystalline solid This describes the physical form and color of the compound.

Solubility

Soluble in organic solvents The compound can dissolve in certain organic solvents, which is important for its use in chemical reactions and applications.

Use as a reagent

Organic synthesis 2,5-bis(4-nitrobenzylidene)cyclopentanone is used as a reagent in organic synthesis, helping to create new compounds through chemical reactions.

Photochromic properties

Yellow to red color change The compound is known for its ability to change color in response to light, which is a key feature in its various applications.

Applications

Photochromic materials and dyes, optical filters, and sensors Due to its color-changing properties, the compound is used in the development of materials and devices that respond to light.

Safety concerns

Potential harmful effects on human health and the environment It is important to handle 2,5-bis(4-nitrobenzylidene)cyclopentanone with care, as it may pose risks to both humans and the environment.

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 120-92-3 cyclopentanone 

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.

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.

Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones

A series of bis-(arylmethylidene)-cycloalkanones was synthesized by cross-aldol condensation. The activity of the compounds was evaluated against amastigotes forms of Trypanosoma cruzi and promastigotes forms of Leishmania amazonensis. The cytotoxicity of the active compounds on uninfected fibroblasts or macrophages was established in vitro to evaluate the selectivity of their antiparasitic effects. Six compounds displayed trypanocidal activity against amastigotes intracellular forms of T. cruzi with IC50 values ranging from 7.0 to 249 μM. Besides these six compounds, eight other molecules exhibited significant leishmanicidal activity (IC50 values ranging from 0.6 to 110.4 μM). Two compounds can be considered as promising antiparasitic lead molecules because they showed IC50 values in the low-micromolar range (≤1.2 μM) with an adequate SI (≥19.9). To understand the mechanism of action of these compounds, two possible molecular targets were investigated: trypanothione reductase (TR) and cruzain.

Aldol condensations of a variety of different aldehydes and ketones under ultrasonic irradiation using poly(N-vinylimidazole) as a new heterogeneous base catalyst under solvent-free conditions in a liquid-solid system

An ultrasound-assisted aldol condensation reaction has been developed for a range of ketones with a variety of aromatic aldehydes using poly(N-vinylimidazole) as a solid base catalyst in a liquid-solid system. The catalyst can be recovered by simple filtration and reused at least 10 times without any significant reduction in its activity. The reaction is also amenable to the large scale, making the procedure potentially useful for industrial applications.

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.

A recyclable fluoroalkylated 1,4-disubstituted [1,2,3]-triazole organocatalyst for aldol condensation of aldehydes and ketones

A new fluoroalkylated 1,4-disubstituted [1,2,3]-triazole was prepared and acted as an organocatalyst for aldol condensation of different ketones with various aldehydes. Aldol condensation proceeded efficiently in the presence of catalytic amount of fluoroalkylated [1,2,3]-triazole. The catalyst could be easily recovered by fluorous solid-phase extraction with excellent purity and reused for three runs with slightly decrease in its activity.

Poly(ethylene)glycol/AlCl3 as a Green and Reusable System in the Synthesis of α,α′'-bis(substituted-benzylidene) Cycloalkanones

Aluminum chloride has been found to be a highly efficient catalyst for the aldol condensation of aldehydes and cycloketones in poly(ethylene)glycol 400 at room temperature. The reaction is very fast, clean and environmentally benign for the synthesis of a variety of α,α′'-bis(substituted- benzylidene) cycloalkanones.

Solvent-free, cross-aldol condensation reaction using silica-supported, phosphorus-containing reagents leading to α,α′-Bis(arylidene) cycloalkanones

This article describes an efficient, simple, and clean method for the synthesis of α,α′-bis(arylidene, furylidene and cinnamylidene)cycloalkanones under solvent-free conditions. The cross-aldol condensation of cycloalkanones with aldehydes in the presence of silica-supported phosphorus pentoxide (P2O5/SiO 2) or silicaphosphinoxide (silphox, [POCl3-n(SiO 2)n]) as heterogeneous reagents produces the title compounds in good to excellent yields. Copyright Taylor & Francis Group, LLC.

Synthesis of α,α′-bis(substitutedbenzylidene) cycloalkanones by a grinding method

KF-Al2O3 catalyses the crossed aldol condensation of various aromatic aldehydes with cycloalkanones, giving corresponding α,α′-bis(substitutedbenzylidene)cycloalkanones under solvent free conditions by a grinding method at room temperature.