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Syntheses and crystal structures of two piperine derivatives.

ABSTRACT: The title compounds, 5-(2H-1,3-benzodioxol-5-yl)-N-cyclo-hexyl-penta-2,4-dienamide, C18H21NO3 (I), and 5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one C16H17NO3 (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 mol-ecules. The extended structure of (I) features N-H?O amide hydrogen bonds, which generate C(4) [010] chains. The crystal of (II) features aromatic ?-? stacking, as for two of three known piperine polymorphs.

SUBMITTER: Ezawa T 

PROVIDER: S-EPMC7199259 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Syntheses and crystal structures of two piperine derivatives.

Ezawa Toshinari T   Inoue Yutaka Y   Murata Isamu I   Suzuki Mitsuaki M   Takao Koichi K   Sugita Yoshiaki Y   Kanamoto Ikuo I  

Acta crystallographica. Section E, Crystallographic communications 20200409 Pt 5

The title compounds, 5-(2<i>H</i>-1,3-benzodioxol-5-yl)-<i>N</i>-cyclo-hexyl-penta-2,4-dienamide, C<sub>18</sub>H<sub>21</sub>NO<sub>3</sub> (I), and 5-(2<i>H</i>-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one C<sub>16</sub>H<sub>17</sub>NO<sub>3</sub> (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 th  ...[more]

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