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两种胡椒碱衍生物的合成与晶体结构

Syntheses and crystal structures of two piperine derivatives.

作者信息

Ezawa Toshinari, Inoue Yutaka, Murata Isamu, Suzuki Mitsuaki, Takao Koichi, Sugita Yoshiaki, Kanamoto Ikuo

机构信息

Faculty of Pharmacy and Pharmaceutical Science, Josai University, 1-1 Keyakidai, Sakado-shi, Saitama, 3500295, Japan.

Faculty of Science, Josai University, 1-1 Keyakidai, Sakado-shi, Saitama, 3500295, Japan.

出版信息

Acta Crystallogr E Crystallogr Commun. 2020 Apr 9;76(Pt 5):646-650. doi: 10.1107/S2056989020004648. eCollection 2020 May 1.

DOI:10.1107/S2056989020004648
PMID:32431925
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7199259/
Abstract

The title compounds, 5-(2-1,3-benzodioxol-5-yl)--cyclo-hexyl-penta-2,4-dienamide, CHNO (I), and 5-(2-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)penta-2,4-dien-1-one CHNO (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 (4) [010] chains. The crystal of (II) features aromatic π-π stacking, as for two of three known piperine polymorphs.

摘要

标题化合物5-(2-1,3-苯并二氧杂环戊烯-5-基)-环己基-戊-2,4-二烯酰胺(CHNO,I)和5-(2-1,3-苯并二氧杂环戊烯-5-基)-1-(吡咯烷-1-基)戊-2,4-二烯-1-酮(CHNO,II)是胡椒碱的衍生物,胡椒碱是胡椒中的一种辛辣成分。它们的几何参数与胡椒碱的三种多晶型物相似,这表明电子在分子长度上发生了共轭。(I)的扩展结构具有N-H⋯O酰胺氢键,形成了(4)[010]链。(II)的晶体具有芳香π-π堆积,与已知的三种胡椒碱多晶型物中的两种情况相同。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/5d2718521431/e-76-00646-fig7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/a3191eadefbb/e-76-00646-fig1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/96e5b08738e6/e-76-00646-fig2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/58a9596e1b61/e-76-00646-fig3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/917f6a603092/e-76-00646-fig4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/b7cffaf58ca8/e-76-00646-fig5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/765ad758318b/e-76-00646-fig6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/5d2718521431/e-76-00646-fig7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/a3191eadefbb/e-76-00646-fig1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/96e5b08738e6/e-76-00646-fig2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/58a9596e1b61/e-76-00646-fig3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/917f6a603092/e-76-00646-fig4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/b7cffaf58ca8/e-76-00646-fig5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/765ad758318b/e-76-00646-fig6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b4db/7199259/5d2718521431/e-76-00646-fig7.jpg

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