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Syntheses and crystal structures of two piperine derivatives. 2020
Toshinari Ezawa, and
Yutaka Inoue, and
Isamu Murata, and
Mitsuaki Suzuki, and
Koichi Takao, and
Yoshiaki Sugita, and
Ikuo Kanamoto
Faculty of Pharmacy and Pharmaceutical Science, Josai University, 1-1 Keyakidai, Sakado-shi, Saitama, 3500295, Japan.
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 π-π stacking, as for two of three known piperine polymorphs.
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