A new approach to the synthesis of pellitorine was written by Ishbaeva, A. U.;Shakhmaev, R. N.;Zorin, V. V.. And the article was included in Bashkirskii Khimicheskii Zhurnal in 2011.Safety of (2E,4E)-N-Isobutyldeca-2,4-dienamide The following contents are mentioned in the article:
The stereoselective method for the synthesis of natural alkaloid pellitorine – (2E,4E)-N-isobutyldeca-2,4-dienamide has been developed using nonphosphine Mizoroki-Heck reaction. A cross-coupling reaction of (E)-1-iodohept-1-ene, obtained by hydroalumination-iodination 1-heptyne, with N-isobutylacrylamide, synthesized by amidation of the acryloyl chloride by isobutylamine, in the presence of Pd(OAc)2, base and tetrabutylammonium chloride in DMF afforded target product in high yield with insignificant content of isomeric compounds (∼1%). The overall yield of pellitorine calculated from 1-heptyne is 79%. This study involved multiple reactions and reactants, such as (2E,4E)-N-Isobutyldeca-2,4-dienamide (cas: 18836-52-7Safety of (2E,4E)-N-Isobutyldeca-2,4-dienamide).
(2E,4E)-N-Isobutyldeca-2,4-dienamide (cas: 18836-52-7) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Safety of (2E,4E)-N-Isobutyldeca-2,4-dienamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics