27687-46-3

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-N-methyl-N,3-diphenylprop-2-enamide is utilized as a starting material for the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the creation of a wide range of molecules with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (2E)-N-methyl-N,3-diphenylprop-2-enamide is employed as a key intermediate for constructing complex organic molecules. Its reactivity and functional groups make it a versatile component in the development of new chemical entities.
Used in Antifungal and Antimicrobial Applications:
(2E)-N-methyl-N,3-diphenylprop-2-enamide has been studied for its potential pharmacological properties, including its use as an antifungal and antimicrobial agent. Its ability to inhibit the growth of certain fungi and bacteria makes it a candidate for further research and development in the area of infectious disease treatment.

Upstream product

• 102-92-1 cinnamoyl chloride 
• 100-61-8 N-methylaniline 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 121-69-7 N,N-dimethyl-aniline 
• 104-55-2 3-phenyl-propenal 
• 538-56-7 cinnamic acid anhydride 
• 621-82-9 Cinnamic acid 
• 100-52-7 benzaldehyde 
• 124-38-9 carbon dioxide 
• 6273-94-5 N-methyl-N-phenylacrylamide 
• 98-80-6 phenylboronic acid 
• 74-88-4 methyl iodide 
• 100-39-0 benzyl bromide 

Downstream Products

• 100-61-8 N-methylaniline 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 854880-24-3 3-phenyl-valeric acid-(N-methyl-anilide) 
• 348611-81-4 3,3-diphenyl-propionic acid-(N-methyl-anilide) 
• 2859-29-2 1-methyl-3-phenylquinolin-2(1H)-one 
• 59181-30-5 3-benzylidene-1H-pyrrolo[2,3-b]pyridin-2(3H)-one 
• 1643771-67-8 methyl 2-methyl-3-(1-methyl-2-oxoindolin-3-yl)-3-phenylpropanoate 

Relevant academic research and scientific papers

Cyclobutane-cleavage of anti-head-to-head coumarin and quinolinone homo- and cross-dimers via single- and two-photon-absorption photochemistry

The light-driven cleavage of cyclobutane containing systems via [2 + 2] cycloreversion, such as di-coumarin, is an important yet poorly investigated photochemical reaction. Its applications can be found in smart crosslinking polymers or light-activated drug release. We report the increased cleavage efficiencies of the coumarins lactam analog quinolinone for single-photon as well as two-photon-absorption experiments. To investigate the structure-function relationship of the molecular substitution pattern and its influence on the photoactivity, a coumarin-quinolinone cross-dimer was synthesized and investigated towards its cleavage efficiencies in single-photon as well as two-photon photocleavage. The cross-dimer shows a lower cleavage efficiency than both homo-dimers. The presented results are of interest, e.g., for applications utilizing highly efficient cleavage reactions in symmetric or asymmetric molecular frameworks.

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.

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides

A catalytic asymmetric conjugate hydrophosphination of α,β-unsaturated amides is accomplished by virtue of the strong nucleophilicity of copper(I)-PPh2 species, which provides an array of chiral phosphines bearing an amide moiety in high to excellent yields with excellent enantioselectivity. Furthermore, the dynamic kinetic resolution of unsymmetrical diarylphosphines (HPAr1Ar2) is successfully carried out through the copper(I)-catalyzed conjugate addition to α,β-unsaturated amides, which affords P-chiral phosphines with good-to-high diastereoselectivity and high enantioselectivity. 1H NMR studies show that the precoordination of HPPh2 to copper(I)-bisphosphine complex is critical for the efficient deprotonation by Barton's Base. Moreover, the relative stability of the copper(I)-(R,RP)-TANIAPHOS complex in the presence of excessive HPPh2, confirmed by 31P NMR studies, is pivotal for the high asymmetric induction, as the ligand exchange between bisphosphine and HPPh2 would significantly reduce the enantioselectivity. At last, a double catalytic asymmetric conjugate hydrophosphination furnishes the corresponding product in high yield with high diastereoselectivity and excellent enantioselectivity, which is transformed to a chiral pincer palladium complex in moderate yield. This chiral palladium complex is demonstrated as an excellent catalyst in the asymmetric conjugate hydrophosphination of chalcone.

Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant

An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.

Synthesis of hydroxyl-containing oxindoles and 3,4-dihydroquinolin-2-ones through oxone-mediated cascade arylhydroxylation of activated alkenes

Hydroxyl-containing compounds are highly value-Added organic molecules, and the establishment of novel methodologies for their elaboration is a long-standing challenge in organic synthesis. Here the first oxone-mediated direct arylhydroxylation of activat

Rh(i)-Catalyzed regioselective arylcarboxylation of acrylamides with arylboronic acids and CO2

The first Rh(i)-catalyzed regioselective arylcarboxylation of electron-deficient acrylamides with arylboronic acids under atmospheric pressure of CO2 has been developed. A range of acrylamides and arylboronic acids were compatible with this reaction under redox-neutral conditions, leading to a series of malonate derivatives that are versatile building blocks in organic syntheses.

Catalyst-Free, Direct Electrochemical Tri- and Difluoroalkylation/Cyclization: Access to Functionalized Oxindoles and Quinolinones

The catalyst-free electrochemical di- and trifluoromethylation/cyclization of N-substituted acrylamides was realized under external oxidant-free conditions. The strategy provides expedient access to fluoroalkylated oxindoles and 3,4-dihydroquinolin-2(1H)-ones with ample scope and broad functional group tolerance by mild, direct electrolysis of sodium sulfinates in an undivided cell. Detailed mechanistic studies provided strong support for a SET-based reaction manifold.

Photocatalytic C-C Bond Activation of Oxime Ester for Acyl Radical Generation and Application

A unified strategy to generate acyl radical from oxime ester via selective C-C bond activation is reported. Under visible-light irradiation, single-electron transfer from fac-Ir(ppy)3 to related oxime takes place followed by a fast β-fragment of C-C bond to yield aryl and aliphatic acyl radicals, subsequently captured by diverse Michael acceptors. More interestingly, the single-electron transfer enables coupling with energy transfer of the excited fac-Ir(ppy)3 via enone intermediate formed in situ for cyclobutane formation.

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.