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Syntheses and crystal structures of two piperine derivatives

The title compounds, 5-(2H-1,3-benzodioxol-5-yl)-N-cyclo­hexyl­penta-2,4-dienamide, C(18)H(21)NO(3) (I), and 5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one C(16)H(17)NO(3) (II), are derivatives of piperine, which is known as a pungent component of pepper. Their geometrical param...

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Detalles Bibliográficos
Autores principales: Ezawa, Toshinari, Inoue, Yutaka, Murata, Isamu, Suzuki, Mitsuaki, Takao, Koichi, Sugita, Yoshiaki, Kanamoto, Ikuo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7199259/
https://www.ncbi.nlm.nih.gov/pubmed/32431925
http://dx.doi.org/10.1107/S2056989020004648
Descripción
Sumario:The title compounds, 5-(2H-1,3-benzodioxol-5-yl)-N-cyclo­hexyl­penta-2,4-dienamide, C(18)H(21)NO(3) (I), and 5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one C(16)H(17)NO(3) (II), are derivatives of piperine, which is known as a pungent component of pepper. Their geometrical parameters are similar to those of the three polymorphs of piperine, which indicate conjugation of electrons over the length of the mol­ecules. The extended structure of (I) features N—H⋯O amide hydrogen bonds, which generate C(4) [010] chains. The crystal of (II) features aromatic π–π stacking, as for two of three known piperine polymorphs.