13565-07-6

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-(4-methylphenyl)acryloyl chloride is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, (2E)-3-(4-methylphenyl)acryloyl chloride serves as a building block for the production of various agrochemicals, such as pesticides and herbicides. Its reactivity enables the creation of effective compounds for crop protection and management.
Used in Polymer Industry:
(2E)-3-(4-methylphenyl)acryloyl chloride is utilized in the polymer industry for the synthesis of polymers with specific properties. Its incorporation into polymer chains can lead to materials with improved characteristics, such as enhanced strength, flexibility, or chemical resistance.

Upstream product

• 1866-39-3 4-methylcinnamic acid 
• 1866-39-3 trans-p-methylcinnamic acid 
• 79-37-8 oxalyl dichloride 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 63346-65-6 C₂₄H₂₉NO₄ 
• 57259-93-5 1-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-4-(3-p-tolyl-acryloyl)-piperazine 
• 7560-43-2 methyl 3-(4-methylphenyl)acrylate 
• 15795-11-6 p-methyl-N-phenylcinnamamide 
• 176690-70-3 N-benzyl-N-<3-(p-tolyl)acryloyl>-1-naphthamide 
• 1186073-39-1 (E)-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)-3-p-tolylacrylamide 
• 511250-70-7 C₁₇H₁₆O₃ 
• 1352448-26-0 2-(4-methylphenyl)vinylcarbamoyl azide 
• 1403694-14-3 1,3,3-tri(-p-tolylpropan-)1-one 

Relevant academic research and scientific papers

Photoredox Cyclization of N-Arylacrylamides for Synthesis of Dihydroquinolinones

Metal- and additive-free photoredox cyclization of N-arylacrylamides is herein reported that provides a concise access to the formation of dihydroquinolinones. In this protocol, sustainable visible light was used as the energy source, and the organic light-emitting molecule 4CzIPN served as the efficient photocatalyst. This reaction system features exclusive 6-endo-trig cyclization selectivity with a generally good yield of a range of functionalized dihydroquinolinones and dihydrobenzoquinolinones. Mechanistical studies reveal the feasibility of both 1,3-H shift and intersystem crossing of the diradical intermediate.

Synthesis of sorbicillinoid analogues with anti-inflammation activities

Recently, we demonstrated potential anti-inflammatory effects of sorbicillinoids isolated from marine fungi. Here, we report the synthesis of a series of new sorbicillinoid analogues and assessed their anti-inflammatory activities. Our results reveal that side chain substitution with (E)-2-butenoyl, (E)-3-(4-fluorophenyl)-2-propenoyl, and (E)-3-(3,4,5-trimethoxyphenyl)-2-propenoyl significantly enhanced the inhibitory effects of the derivatives on nitric oxide (NO) production and inducible NO synthesis (iNOS) expression stimulated by lipopolysaccharides (LPS) in mouse macrophage. Further chemical derivatization shows that the monomethylresorcinol skeleton worked better than the dimethylresorcinol skeleton in inhibiting LPS-induced inflammatory response in cultured cells. Among the 29 synthesized sorbicillinoid analogues, compounds 4b and 12b exhibited the strongest anti-inflammatory activities, holding the promise of being developed into lead compounds that can be explored as potent anti-inflammation agents.

Antifungal Exploration of Quinoline Derivatives against Phytopathogenic Fungi Inspired by Quinine Alkaloids

Enlightened from our previous work of structural simplification of quinine and innovative application of natural products against phytopathogenic fungi, lead structure 2,8-bis(trifluoromethyl)-4-quinolinol (3) was selected to be a candidate and its diversified design, synthesis, and antifungal evaluation were carried out. All of the synthesized compounds Aa1-Db1 were evaluated for their antifungal activity against four agriculturally important fungi, Botrytis cinerea, Fusarium graminearum, Rhizoctonia solani, and Sclerotinia sclerotiorum. Results showed that compounds Ac3, Ac4, Ac7, Ac9, Ac12, Bb1, Bb10, Bb11, Bb13, Cb1. and Cb3 exhibited a good antifungal effect, especially Ac12 had the most potent activity with EC50 values of 0.52 and 0.50 μg/mL against S. sclerotiorum and B. cinerea, respectively, which were more potent than those of the lead compound 3 (1.72 and 1.89 μg/mL) and commercial fungicides azoxystrobin (both >30 μg/mL) and 8-hydroxyquinoline (2.12 and 5.28 μg/mL). Moreover, compound Ac12 displayed excellent in vivo antifungal activity, which was comparable in activity to the commercial fungicide boscalid. The preliminary mechanism revealed that compound Ac12 might cause an abnormal morphology of cell membranes, an increase in membrane permeability, and release of cellular contents. These results indicated that compound Ac12 displayed superior in vitro and in vivo fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.

Design, Synthesis, Structure-Activity Relationship, Molecular Docking, and Herbicidal Evaluation of 2-Cinnamoyl-3-Hydroxycyclohex-2-en-1-one Derivatives as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

Cinnamic acid, isolated from cinnamon bark, is a natural product with excellent bioactivity, and it effectively binds with cyclohexanedione to form novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors. According to the active sub-structure combinat

Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes

β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

Practical access to fluorescent 2,3-naphthalimide derivatives: Via didehydro-Diels-Alder reaction

A practical and efficient approach for the synthesis of fluorescent 2,3-naphthalimide derivatives has been developed from readily available starting materials via an intramolecular didehydro-Diels-Alder reaction, which proceeded well under room temperature, exhibiting a wide substrate scope and good functional group tolerance. The practicability of this methodology has been verified by one-step synthesis of the environmentally sensitive fluorophore 6-DMN on a gram scale with a shorter time, fewer steps and less waste disposal, and without the utilization of toxic transition metals. The present experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.

Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes

We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.

Synthesis and biological evaluation of coumarin derivatives as α-glucosidase inhibitors

In this study, two series of coumarin derivatives 5a～i and 6a～i were synthesized, and their inhibitory activity against α-glucosidase was determined. The results indicated that most of the synthesized derivatives exhibited prominent inhibitory activities

Coumarin derivative as well as preparation method and application thereof

The invention discloses a coumarin derivative as well as a preparation method and application thereof. The chemical structural formula of the coumarin derivative is represented by a formula (I) or a formula (II), wherein in the formula, R1 is H, CH3, OCH3

Benzo[d]isothiazole-3-(2H)-one derivative, preparation method and application thereof

The invention relates to a benzo[d]isothiazole-3-(2H)-one derivative, a preparation method and application of the benzo[d]isothiazole-3-(2H)-one derivative. The compound is a free alkali or salt of acompound with a structure shown in a general formula (I). The salt is one of hydrochloride, hydrobromide, sulfate, trifluoroacetate, tartrate, lactate or mesylate; R1 independently represents "-CH2-CO-" or "-CH2-CH2-"; R2 independently represents "-CH2-CH2-O-" or "-CO-CH=CH-"; R3 independently represents hydrogen, halogens, a hydrocarbon group, a halogen-substituted hydrocarbon group, a nitro group, an amino group, a nitrile group, a hydroxyl group, an alkoxy group, an aryloxy group, a heterocycloalkoxy group, an aryl group, a substituted heterocyclic ring or a substituted aryl group. The invention also provides an application of the benzo[d]isothiazole-3-(2H)-one derivative in preparation of ischemic stroke treatment medicines.