80783-99-9

Basic information

• Product Name: 2-Propenamide, N-methoxy-N-methyl-3-phenyl-
• Synonyms: (2E)-N-methoxy-N-methyl-3-phenylacrylamide;(E)-N-methoxy-N-methyl-3-phenyl-2-propenamide;(2E)-N-methoxy-N-methyl-3-phenylpropenamide;(E)-N-methoxy-N-methyl-3-phenylprop-2-enamide;3-phenyl-(N-methoxy-N-methyl)propene amide;N-methoxy-N-methyl-(E)-3-phenyl-2-propenamide
• CAS NO: 80783-99-9
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.23
• Mol File: 80783-99-9.mol
• Article Data: 75

Chemical Properties

• Boiling Point: 274.9±33.0 °C(Predicted)
• Density: 1.098±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Propenamide, N-methoxy-N-methyl-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, N-methoxy-N-methyl-3-phenyl-(80783-99-9)
• EPA Substance Registry System: 2-Propenamide, N-methoxy-N-methyl-3-phenyl-(80783-99-9)

Safety Data

• Hazardous Substances Data: 80783-99-9(Hazardous Substances Data)

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

• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 30289-28-2 N-methoxy-N-methylcarbamoyl chloride 
• 100-52-7 benzaldehyde 
• 367508-01-8 diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate 
• 102-92-1 Cinnamoyl chloride 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 908863-61-6 2-(benzo[d]thiazol-2-ylsulfonyl)-N-methoxy-N-methylacetamide 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 621-82-9 Cinnamic acid 
• 102-92-1 cinnamoyl chloride 
• 124931-12-0 diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 170646-96-5 N-methoxy-N-methyl-3-phenylpropionamide 

Downstream Products

• 91897-73-3 (1E,4E)-1-phenyl-1,4-hexadien-3-one 
• 2757-10-0 N-methylcinnamamide 
• 89176-05-6 (E)-4,4,5,5,5-pentafluoro-1-phenylpent-1-en-3-one 
• 1170697-34-3 C₁₄H₁₉NO₂ 
• 19184-21-5 (E)-1-phenylhept-1-en-3-one 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 940-43-2 N-methyl-3-phenylpropanamide 
• 1396465-39-6 C₁₇H₁₇NO₂ 
• 1396465-85-2 C₁₈H₁₉NO₂ 
• 1396465-61-4 C₁₉H₂₁NO₂ 
• 1396466-08-2 C₁₉H₂₁NO₂ 
• 1396465-48-7 C₁₉H₂₁NO₂ 
• 1396466-38-8 C₁₈H₁₉NO₂ 
• 1396465-73-8 C₁₈H₁₉NO₂ 

Relevant articles and documents

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.

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.

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.