80783-99-9

Usage

Also Known As

N-Methoxy-N-methyl-3-phenylacrylamide

Primary Use

Production of pharmaceuticals and agrochemicals

Physical Characteristics

Clear, colorless to yellowish liquid
Faint odor

Solubility

Soluble in water and organic solvents

Classification

Tertiary amide

Applications

Intermediate in the synthesis of various organic compounds

Safety Precautions

Handle with caution
Harmful if swallowed, inhaled, or absorbed through the skin
May cause irritation to eyes and skin

Upstream product

• 124931-12-0 diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate 
• 100-52-7 benzaldehyde 
• 100-42-5 styrene 
• 193634-77-4 N-methoxy-N-methylacrylamide 
• 908863-61-6 2-(benzo[d]thiazol-2-ylsulfonyl)-N-methoxy-N-methylacetamide 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 108-86-1 bromobenzene 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 103-26-4 Methyl cinnamate 
• 1068-55-9 isopropylmagnesium chloride 
• 170646-96-5 N-methoxy-N-methyl-3-phenylpropionamide 
• 591-50-4 iodobenzene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 103-26-4 methyl cinnamate 

Downstream Products

• 121712-56-9 (E)-tert-butyl 3,5-dioxo-7-phenylhept-6-enoate 
• 1896-62-4 (E)-benzalacetone 
• 91897-73-3 (1E,4E)-1-phenyl-1,4-hexadien-3-one 
• 89176-05-6 (E)-4,4,5,5,5-pentafluoro-1-phenylpent-1-en-3-one 
• 25294-56-8 (1E)-6-hydroxy-6-methyl-1-phenyl-1-hepten-4-yn-3-one 
• 84319-68-6 (E)-4-methyl-1-phenylhex-1-en-3-one 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 73291-51-7 (E)-1-phenylpenta-1,4-dien-3-one 
• 37401-88-0 (E)-1-phenyl-1-penten-4-yn-3-one 
• 2757-10-0 (E)-N-methyl-3-phenyl-acrylamide 
• 37166-60-2 (1E)-1-phenyl-5-(trimethylsilyl)pent-1-en-4-yn-3-one 
• 37845-36-6 (E)-1,5-diphenyl-1-penten-4-yn-3-one 
• 1170697-34-3 C₁₄H₁₉NO₂ 
• 1396465-39-6 C₁₇H₁₇NO₂ 

Relevant academic research and scientific papers

Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation

Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields (58–80%). The utility of this methodology was exemplified by the stereoselective construction of desmethoxyyangonin, asnipyrone A, and asnipyrone B.

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water

Host-guest assemblies of a designed 1,4-bis(diarylamino)naphthalene and V-shaped aromatic amphiphiles consisting of two pentamethylbenzene moieties bridged by an m -phenylene unit bearing two hydrophilic side chains emerged as highly reducing photoredox catalysis systems in water. An efficient demethoxylative hydrogen transfer of Weinreb amides has been developed. The present supramolecular strategy permits facile tuning of visible-light photoredox catalysis in water.

Cooperative Lewis Acid Catalysis for the Enantioselective C(sp3)-H Bond Functionalizations of 2-Alkyl Azaarenes

Herein, we describe the enantioselective C(sp3)-H bond functionalizations of 2-alkyl azaarenes using a cooperative dual Lewis acid catalysis. An achiral Lewis acid activates the unactivated azaarene partner without the need for a strong base. Orthogonally, a chiral-at-metal Lewis acid catalyst enables LUMO lowering and induces chirality. This method tolerates a range of complex molecular scaffolds and exhibits good to excellent yields and selectivity while accepting a wide variety of functional groups.

Discovery of CAPE derivatives as dual EGFR and CSK inhibitors with anticancer activity in a murine model of hepatocellular carcinoma

Caffeic acid phenethyl ester (CAPE), a bioactive component extracted from propolis of honeybee hives, can inhibit hepatocellular carcinoma (HCC). In order to explore more stable CAPE derivatives, 25 compounds were designed, synthesized, and pharmacologically assessed in vitro and in vivo as anti-tumor agents in HCC. Compounds 8d, 8f, 8l, 8j, and 8k showed favorable antiproliferative activity than other compounds including CAPE in the HCC cell lines. Based on the result of QTRP (Quantitative Thiol Reactivity Profiling), epidermal growth factor receptor (EGFR) and C-terminal Src kinase (CSK) were supposed to the targets of 8f, which was confirmed by binding mode analysis. Furthermore, compounds 8f, 8l, 8j, 8k, 8g, and 8h showed potent inhibitory effects against both CSK and EGFR than other derivatives in an ADP-Glo kinase assay. The representative compound, 8f, potently inhibited various tumor growth in murine model including murine hepatocellular carcinoma H22, meanwhile downregulating the EGFR/AKT pathway and enhancing T cell proliferation through inhibition of CSK. Metabolic stability in vitro suggested 8f and 8k were more stable in mouse plasma than CAPE and susceptible to metabolism in liver microsomes. The overall excellent profile of compound 8f makes it a potential candidate for further preclinical investigation.

Fluoro-Substituted Methyllithium Chemistry: External Quenching Method Using Flow Microreactors

The external quenching method based on flow microreactors allows the generation and use of short-lived fluoro-substituted methyllithium reagents, such as fluoromethyllithium, fluoroiodomethyllithium, and fluoroiodostannylmethyllithium. Highly chemoselective reactions have been developed, opening new opportunities in the synthesis of fluorinated molecules using fluorinated organometallics.

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.

Radical-Cation Vinylcyclopropane Rearrangements by TiO2Photocatalysis

Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations.

Phenethyl caffeate derivative, preparation method, pharmaceutical composition and application thereof

The invention discloses a phenethyl caffeate derivative, a preparation method, a pharmaceutical composition and application thereof. Specifically, the invention relates to a compound shown as formula(I) or an isomer and pharmaceutically acceptable salt th

Selective Reduction of α,β-Unsaturated Weinreb Amides in the Presence of α,β-Unsaturated Esters

α,β-Unsaturated esters were selectively protected in situ in the presence of α,β-unsaturated Weinreb amides using PEt3 and trimethylsilyl trifluoromethanesulfonate (TMSOTf) in toluene under reflux. Diisobutylaluminium hydride (DIBAL-H) reduction of the mixture followed by tetra-n-butylammonium fluoride (TBAF) treatment produced α,β-unsaturated aldehydes in good yields along with the recovered α,β-unsaturated esters.