Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formed via alkene metathesis from either a triene or a tetraene precursor.

IF 0.8 4区化学

Acta crystallographica. Section C, Crystal structure communications Pub Date : 2013-11-01 Epub Date: 2013-10-09 DOI:10.1107/S010827011302492X

Keith G Andrews, Christopher S Frampton, Alan C Spivey

引用次数: 3

Abstract

The identity of the major product of Ru-catalysed alkene metathesis of two polyene substrates has been determined using density functional theory (DFT) NMR prediction, a (1)H-(1)H Total Correlated Spectroscopy (TOCSY) NMR experiment and ultimately by single-crystal X-ray crystallography. The substrates were designed as those that would potentially allow expedient access to the trans-decalin skeleton of the natural product (-)-euonyminol, but the product was found to be a bis-cyclopentenyl-β-cyanohydrin [1-(1-hydroxycyclopent-3-en-1-yl)cyclopent-3-ene-1-carbonitrile, C11H13NO] rather than the trans-2,3,6,7-dehydrodecalin-β-cyanohydrin.

查看原文本刊更多论文

由三烯或四烯前体通过烯烃复分解形成的双环戊基β-氰丙烷的结构配位。

通过密度泛函理论(DFT)核磁共振预测、(1)H-(1)H全相关光谱(TOCSY)核磁共振实验和最终的单晶x射线晶体学，确定了两种多烯底物的钌催化烯烃复分解的主要产物的身份。底物被设计成可能方便地接近天然产物(-)-euonyminol的反式十烷骨架，但产物被发现是双环戊基-β-氰醇[1-(1-羟基环戊基-3-烯-1-基)环戊基-3-烯-1-碳腈，C11H13NO]，而不是反式-2,3,6,7-脱氢十烷基-β-氰醇。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Acta crystallographica. Section C, Crystal structure communications 化学-晶体学

自引率

12.50%

发文量

审稿时长

1 months

期刊介绍： Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.