二乙酰-2-甲基-4,6-双（苯乙基）四氢- 2h -吡喃-2-乙酸酯的自组装和结构

IF 1.2 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR

Journal of Structural Chemistry Pub Date : 2025-03-28 DOI:10.1134/S0022476625030023

S. A. Sokov, A. V. Vologzhanina, A. A. Golovanov

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引用次数: 0

摘要

在1,8-重氮双环[5.4.0]十一-7-烯的催化下，苯丙基醛与乙酰丙酮在乙腈中发生了非同寻常的缩合反应。在室温下生成(2S,3S,4S,5S,6S)-和(2R,3R,4R,5R,6R)-3,5-二乙酰-2-甲基-4,6-二（苯乙基）四氢- 2h -吡喃-2-乙酸酯的外消旋混合物，而不是预期的3-（3-苯基-2-in-1-乙基）戊烷-2,4-二酮。该化合物的分子和晶体结构的x射线衍射和核磁共振研究表明，相对于六元杂环，乙酰氧基的轴向位置表现出一种计量效应。

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Self-Assembly and Structure of Diacetyl-2-Methyl-4,6-bis(phenylethynyl)Tetrahydro-2H-Pyran-2-Ylacetate

Unusual condensation of phenylpropargyl aldehyde with acetylacetone in acetonitrile in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene as a catalyst is described. It proceeds at room temperature with the formation of a racemic mixture of (2S,3S,4S,5S,6S)- and (2R,3R,4R,5R,6R)-3,5-diacetyl-2-methyl-4,6-bis(phenylethynyl)tetrahydro-2H-pyran-2-ylacetate instead of expected 3-(3-phenylprop-2-in-1-ylidene)pentane-2,4-dione. The X-ray diffraction and NMR studies of the molecular and crystal structures of this compound reveals an anometric effect that manifests itself at the axial position of the acetoxy group relative to the six-membered heterocycle.

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来源期刊

Journal of Structural Chemistry 化学-无机化学与核化学

CiteScore

1.60

自引率

12.50%

发文量

142

审稿时长

8.3 months

期刊介绍： Journal is an interdisciplinary publication covering all aspects of structural chemistry, including the theory of molecular structure and chemical bond; the use of physical methods to study the electronic and spatial structure of chemical species; structural features of liquids, solutions, surfaces, supramolecular systems, nano- and solid materials; and the crystal structure of solids.