The crystal and molecular structure of N-(3,4,5-trimethoxycinnamoyl)-Δ3-piperidine-2-one, an amide alkaloid (piperlongumine), C17H19NO5
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Published:1986-05-01
Issue:5
Volume:64
Page:876-880
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ISSN:0008-4042
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Container-title:Canadian Journal of Chemistry
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language:en
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Short-container-title:Can. J. Chem.
Author:
Banerjee Tapati,Chaudhuri Siddhartha
Abstract
The crystals of C17H19NO5 belong to the monoclinic space group P21/n with a = 15.793(3), b = 4.089(4), c = 24.649(5) Å, β = 97.56(3)° V = 157 8(2) Å3, and Z = 4. The structure was solved by MULTAN 78 and refined by full-matrix least-squares to a final R of 0.053 for 1863 observed reflections. X-ray crystallography has revealed that the molecule is the Δ3 isomer and not the Δ5 isomer suggested originally from nmr spectroscopy. The piperidyl nitrogen is sp2 hybridized with its electron lone pair involved in conjugation with the carbonyl groups. The piperidone ring adopts a distorted boat conformation. An interesting feature of the structure is the formation of two C(ethylenic)—H … O(keto) intramolecular hydrogen bonds which stabilize the molecular conformation.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
13 articles.
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