Single-crystal X-ray diffraction analysis and mechanistic implications of (2R,3R)-2-(2-phenoxyethyl)tetrahydrofuran-3-yl acetate.

IF 1.1 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Acta Crystallographica Section C Structural Chemistry Pub Date : 2025-12-01 Epub Date: 2025-11-26 DOI:10.1107/S2053229625010150

Steven P Kelley, Appasaheb K Nirpal, Shyam Sathyamoorthi

引用次数: 0

Abstract

Our laboratory recently explored a highly stereospecific rearrangement of epoxides into tetrahydrofurans. To unambiguously determine the stereochemical outcome of this rearrangement, single crystals of one of the products, (2R*,3R*)-2-(2-phenoxyethyl)tetrahydrofuran-3-yl acetate, C₁₄H₁₈O₄, were grown and analyzed. Based on the crystal structure data, we were able to show that the contiguous stereocenters of this molecule are in a syn configuration, and we now suggest with confidence a plausible mechanism for the rearrangement reaction. The syn configuration of the ring may also account for the inability of most members of this class to crystallize, as it imparts a kink in the structure reminiscent of low-melting unsaturated fatty acids.

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（2R*,3R*）-2-（2-苯氧乙基）四氢呋喃-3-乙酸酯的单晶x射线衍射分析及其机理

我们的实验室最近探索了一种高度立体定向的环氧化物重排成四氢呋喃。为了明确确定这种重排的立体化学结果，我们生长并分析了其中一种产物(2R*,3R*)-2-（2-苯氧乙基）四氢呋喃-3-乙酸酯C14H18O4的单晶。基于晶体结构数据，我们能够证明该分子的连续立体中心处于同步构型，我们现在有信心地提出了重排反应的合理机制。环的同步构型也可以解释这类化合物大多数成员无法结晶的原因，因为它在结构上赋予了一种让人想起低熔点不饱和脂肪酸的扭结。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Acta Crystallographica Section C Structural Chemistry CHEMISTRY, MULTIDISCIPLINARYCRYSTALLOGRAPH-CRYSTALLOGRAPHY

CiteScore

1.60

自引率

12.50%

发文量

148

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.

Single-crystal X-ray diffraction analysis and mechanistic implications of (2R*,3R*)-2-(2-phenoxyethyl)tetrahydrofuran-3-yl acetate.

Abstract

Single-crystal X-ray diffraction analysis and mechanistic implications of (2R,3R)-2-(2-phenoxyethyl)tetrahydrofuran-3-yl acetate.