3695-95-2

Upstream product

• 141-52-6 sodium ethanolate 
• 555-21-5 4-Nitrophenylacetonitrile 
• 100-52-7 benzaldehyde 
• 85613-79-2 C₁₉H₁₈N₃O₃^(1-)*H⁽¹⁺⁾ 

Downstream Products

• 66998-56-9 2-(4-aminophenyl)-3-phenylacrylonitrile 
• 61638-16-2 2-(4-nitrophenyl)-3-phenylpropanenitrile 
• 555-21-5 4-Nitrophenylacetonitrile 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

An Organic Crystal with High Elasticity at an Ultra-Low Temperature (77 K) and Shapeability at High Temperatures

Organic single crystals with elastic bending capability and potential applications in flexible devices and sensors have been elucidated. Exploring the temperature compatibility of elasticity is essential for defining application boundaries of elastic mate

Fluorescence Regulation and Photoresponsivity in AIEE Supramolecular Gels Based on a Cyanostilbene Modified Benzene-1,3,5-Tricarboxamide Derivative

Supramolecular interactions play an important role in regulating the optical properties of molecular materials. Different arrangements of identical molecules can afford a more straightforward insight into the contributions of supramolecular interactions.

Highly active g-C3N4 as a solid base catalyst for knoevenagel condensation reaction under phase transfer conditions

In a promising approach, heterogeneous g-C3N4 as a solid base catalyst exhibits appreciable activity in Knoevenagel condensations at room temperature for the synthesis of substituted stilbene in presence of a crown-ether phase transfer catalyst. High yield of the product substituted stilbene were isolated in a very short reaction time period (～30 min). The solid base g-C3N4 catalyst was proven to be recyclable for several runs. Various aromatic substrates were screened using heterogeneous base g-C3N4 catalyst, exhibiting appreciable corresponding product yield (～99%) at room temperature.

Synthesis of non-symmetrical 3,4-diaryl-substituted pyrroles: Implementation for the preparation of lamellarin R

A straightforward method for synthesising symmetrical and non-symmetrical 3,4-diaryl-substituted pyrroles is proposed, consisting of (i) the condensation reaction between phenylacetonitriles and aldehydes to give acrylonitriles, (ii) the conjugate additio

Application of group v polyoxometalate as an efficient base catalyst: A case study of decaniobate clusters

The base catalytic activity of the decaniobate cluster (TMA)6[Nb10O28]·6H2O (TMA+ = tetramethylammonium cation) was studied theoretically and experimentally. Density functional theory calculations showed that the oxygen atoms in the cluster are highly negatively charged and suggested the possibility that the cluster can act as a base catalyst. We demonstrated for the first time that [Nb10O28]6- actually exhibits base catalytic activity for aldol-type condensation reactions including Knoevenagel and Claisen-Schmidt condensation reactions. The catalytic reactions proceeded under ambient conditions, suggesting that [Nb10O28]6- holds promise as a practical strong base catalyst.

Synthesis and evaluation of (Z)-2,3-diphenylacrylonitrile analogs as anti-cancer and anti-microbial agents

In the present study, a series of (Z)-2,3-diphenylacrylonitrile analogs were synthesized and then evaluated in terms of their cytotoxic activities against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15), as well as anti-microbial activities against three microbes, e.g. Staphylococcus aureus, Salmonella typhi, and Aspergillus niger. The title compounds were synthesized by Knoevenagel condensation reaction of benzyl cyanide or p-nitrobenzyl cyanide with substituted benzaldehydes in good yields. Most of the compounds exhibited significant suppressive activities against the growth of all cancer cell lines. Compound 3c was most active in inhibiting the growth of A549, SK-OV-3, SK-MEL-2, and HCT15 cells lines with IC50 values of 0.57, 0.14, 0.65, and 0.34 mg/mL, respectively, followed by compounds 3f, 3i, and 3h. Compound 3c exhibited 2.4 times greater cytotoxic activity against HCT15 cells, whereas it showed similar potency against SK-OV-3 cells to that of the standard anti-cancer agent doxorubicin. Structure-activity relationship study revealed that electron-donating groups at the para-position of phenyl ring B were more favorable for improved cytotoxic activity, whereas the presence of electron-withdrawing groups was unfavorable compare to unsubstituted acrylonitrile. An optimal electron density on phenyl ring A of (Z)-2,3-diphenylacrylonitrile analogs was crucial for their cytotoxic activities against human cancer cell lines used in the present study. Qualitative structure-cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between calculated polar surface area (PSA), a lipophobic parameter, and cytotoxic activity was found. Moreover, all compounds showed significant anti-bacterial activities against S. typhi, whereas compound 3k showed potent inhibition against both S. aureus and S. typhi bacterial strains.

Efficient and reusable amine-functionalized polyacrylonitrile fiber catalysts for Knoevenagel condensation in water

A series of new fiber catalysts has been synthesized by aminating a commercially available polyacrylonitrile fiber with polyamines such as diethylenetriamine and triethylenetetramine. These fiber catalysts can efficiently catalyze the Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate in water (yields: 95-98%). The triethylenetetramine aminated fiber catalyst was used to catalyze the condensations of a wide range of aromatic aldehydes and active methylene compounds and in each case, this catalyst performed well with yields higher than 93%. This fiber catalyst also exhibited excellent reusability (up to 21 times) and photostability.

Direct amino acid-catalyzed cascade reductive alkylation of arylacetonitriles: High-yielding synthesis of ibuprofen analogs

A novel approach for a one-pot, three-component reductive alkylation (TCRA) reaction of arylacetonitriles-containing electron-withdrawing groups with aldehydes/ketones and 1,4-dihydropyridine via iminium-catalysis has been developed. Many TCRA reaction products have direct applications in agricultural and pharmaceutical chemistry.

Synthesis, characterisation and photophysical properties of a,a-diaryl-acrylonitrile derivatives

a,b-Diarylacrylonitrile derivatives can be prepared by two different routes: (1) the intermolecular condensation of the same arylacetonitriles (2) the condensation of arylaldehydes and arylacetonitriles with a catalytic amount of NaOCH3 at room temperature. Several a,b-diarylacrylonitrile derivatives have been synthesised in this paper and characterised. The UV-vis absorption and photoluminescent (PL) spectra of the products were investigated.

Condensation reactions in water of active methylene compounds with arylaldehydes. One-pot synthesis of flavonols

The condensation reactions of acetophenone, cyclohexanone, isophorone, phenylacetonitrile, p-nitrophenylacetonitrile, (phenylsulfonyl)acetonitrile and indene with benzaldehyde were studied in water heterogeneous phase in the presence and absence of anionic and cationic surfactants such as SLS, CTACl, (CTA)2SO4 and CTAOH. All the reactions occur with excellent yields. The cationic surfactants favour the reaction and the comparison with the corresponding tetrabutylammonium salts show that the micellar catalysis is effective mainly towards the dehydration reaction following that of condensation. Anionic surfactant SLS is inactive. 2'-hydroxychalcones were prepared in aqueous medium in good-excellent yields and the one-pot synthesis of 7- and 3',4'-substituted flavonols was achieved.