495-86-3

Basic information

• Product Name: (2E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide
• Synonyms: (2E)-3-(1,3-Benzodioxol-5-yl)-N-isobutylacrylamide; 2-Propenamide, 3- (1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (E)-; 2-propenamide, 3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (2E)-; 60045-88-7; Cinnamamide, N-isobutyl-3,4-(methylenedioxy)-, (E)-; N1-isobutyl-3-(1,3-benzodioxol-5-yl)acrylamide
• CAS NO: 495-86-3
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.2897
• Mol File: 495-86-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 441.4°C at 760 mmHg
• Flash Point: 220.8°C
• Density: 1.155g/cm³
• Vapor Pressure: 5.45E-08mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: (2E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide(495-86-3)
• EPA Substance Registry System: (2E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide(495-86-3)

Safety Data

• Hazardous Substances Data: 495-86-3(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide" is an amide derivative with a molecular formula of C15H19NO3. It contains a benzodioxole ring and a propenamide functional group. The compound is an enantiomer with a trans configuration at the C=C bond. This chemical may have potential applications in medicinal chemistry, particularly in the development of pharmaceuticals and drug discovery. Further research and investigation are needed to fully understand the properties and potential uses of this compound.

Upstream product

• 78-81-9 isobutylamine 
• 74058-80-3 3-(3,4-methylenedioxycinnamoyl)-1,3-thiazolidine-2-thione 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 96249-87-5 (E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride 
• 2033-24-1 cycl-isopropylidene malonate 
• 120-57-0 piperonal 
• 73818-55-0 Bestmann ylide 
• 96249-87-5 3-benzo[1,3]dioxol-5-yl-acryloyl chloride 

Downstream Products

• 120-57-0 piperonal 
• 94-53-1 Piperonylic acid 

Relevant articles and documents

Rapid access to cinnamamides and piper amides: Via three component coupling of arylaldehydes, amines, and Meldrum's acid

A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation of undesired chemical wastes that generally originate from the use of coupling reagents, oxidants, or catalysts has been avoided to make this reaction more atom economical.

Synthesis of Analogs of Trans-Fagaramide and Their Cytotoxic Activity

A series of 30 compounds were synthetized inspired by active trans-fagaramide structure skeleton. On this synthetic platform, 18 compounds were achieved via Knoevenagel condensation using maleic acid and piperonal, followed by peptide coupling with various amines, giving an average yield of 54%. Subsequently, nine compounds were obtained by palladium-mediated Heck coupling with an average yield of 79%. In addition, cytotoxic activity was evaluated against cardiomyoblast H9c2, breast adenocarcinoma MCF7, hepatocellular carcinoma HepG2, and glioblastoma U-87 cells. The results revealed two aryl halogen-substituted compounds moderately active against H9c2 and MCF7 with IC50 values > 50 μM. One functionalized coumarin showed inhibitory activity against H9c2 (IC50 > 50 μM). In contrast, p-aminophenyl-β-monosubstituted trans-fagaramide was found to inhibit MCF7 (IC50 > 50 μM) without showing toxicity against H9c2 cells.

Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

Selective formation of (E)-α,β-unsaturated amides by intermolecular three-component reaction between aldehydes, amines (1° or 2°) and ketenylidenetriphenylphosphorane (Ph3P=C=C=O) is described. Natural amides such as fagaramide and piperines could be prepared from immediately available educts. The method is shown to be extendable to the preparation of thioesters from thiols and aldehydes.