Lansiumamide A

Base Information

• Chemical Name: Lansiumamide A
• CAS No.: 121817-36-5
• Molecular Formula: C17H15 N O
• Molecular Weight: 249.312
• DSSTox Substance ID: DTXSID401219979
• Metabolomics Workbench ID: 48250
• Nikkaji Number: J1.315.528C,J3.485.278B
• Wikidata: Q76421502
• Mol file: 121817-36-5.mol

Synonyms:Lansiumamide A;N-cis-Styrylcinnamamide;CHEBI:180742;DTXSID401219979;121817-36-5;(E)-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide;(2E)-3-Phenyl-N-[(1Z)-2-phenylethenyl]-2-propenamide;(2E)-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

Chemical Property of Lansiumamide A

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 249.115364102
• Heavy Atom Count: 19
• Complexity: 320

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)NC=CC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C(=O)N/C=C\C2=CC=CC=C2

Technology Process of Lansiumamide A

There total 43 articles about Lansiumamide A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

cinnamamide (621-79-4,22031-64-7) + phenylacetylene (536-74-3) → (2E)-3-phenyl-N-[(Z)-2-phenylvinyl]acrylamide (121817-36-5)

Guidance literature:

With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 1,4-bis(dicyclohexylphosphino)butane; water; ytterbium(III) triflate; In N,N-dimethyl-formamide; at 60 ℃; for 6h; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0029-1216847

Reference yield: 88.0%

[(E)-2-bromoethenyl]benzene (588-72-7,1340-14-3) + cinnamamide (621-79-4,22031-64-7) → (2E)-3-phenyl-N-[(E)-2-phenylvinyl]acrylamide (121817-36-5)

Guidance literature:

With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In tetrahydrofuran; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jo301332s

Reference yield: 85.0%

cinnamamide (621-79-4,22031-64-7) + (Z)-styryl iodide (57918-63-5) → (2E)-3-phenyl-N-[(Z)-2-phenylvinyl]acrylamide (121817-36-5)

Guidance literature:

With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In tetrahydrofuran; at 60 ℃; for 3h; Schlenk technique; Inert atmosphere;

DOI:10.3390/molecules24203764

upstream raw materials:

(E)-1-isocyanato-2-phenylethene

(E)-(2-phenylethenyl)magnesium bromide

cis-cinnamic acid

methyl iodide

Downstream raw materials:

(2E)-N-methyl-3-phenyl-N-[(E)-2-phenylvinyl]acrylamide

(2E)-N-methyl-3-phenyl-N-[(Z)-2-phenylvinyl]acrylamide

5-phenyl-2-[(E)-2-phenylethenyl]-1,3-oxazole

Refernces

• 1、 Pasqua, Adele E.,Ferrari, Frank D.,Crawford, James J.,Marquez, Rodolfo. "Total synthesis of lansiumamides A and B and alatamide". . p. 6042 - 6043. Retrieved 2014.
• 2、 Cheung, Chi Wai,Buchwald, Stephen L.. "Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization". . p. 7526 - 7537. Retrieved 2012/10/30.