23512-49-4

Basic information

• Product Name: (2Z)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide
• CAS NO: 23512-49-4
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.2897
• Mol File: 23512-49-4.mol
• Article Data: 9

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: (2Z)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide(23512-49-4)
• EPA Substance Registry System: (2Z)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide(23512-49-4)

Safety Data

• Hazardous Substances Data: 23512-49-4(Hazardous Substances Data)

Upstream product

• 96249-87-5 3-benzo[1,3]dioxol-5-yl-acryloyl chloride 
• 78-81-9 isobutylamine 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 96249-87-5 (E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride 
• 1417353-80-0 3,4-methylenedioxy-5-trifluoromethylbenzaldehyde 
• 1417353-79-7 5'-trifluoromethyl-3',4'-methylenedioxy cinnamic acid 
• 124-40-3 dimethyl amine 
• 2373-80-0 3,4-(methylenedioxy)cinnamic acid 
• 2033-24-1 cycl-isopropylidene malonate 
• 120-57-0 piperonal 
• 73818-55-0 Bestmann ylide 
• 74058-80-3 3-(3,4-methylenedioxycinnamoyl)-1,3-thiazolidine-2-thione 

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.

SUBSTITUTED CINNAMAMIDE DERIVATIVE, PREPARATION METHOD AND USE THEREOF

The present invention relates to substituted cinnamamide derivatives, the method for preparing thereof and the use thereof. Each of said derivatives has a structure of formula (I). The method for preparing the substituted cinnamamides and their derivatives of the present invention is also disclosed. Substituted piperonal derivatives are selected as starting materials to prepare the substituted cinnamamide derivatives of the present invention by Wittig reaction and acid-amine condensation reaction. Further, a use of the present compounds in preventing and treating depressive-type mental diseases is disclosed.