Synthesis and Solid-State Dynamics of a Crystalline Steroid Molecular Rotor without the Alkyne Axle: Steroid Dimers Based on a 1,4-Di(1,3-dioxan-2-yl)benzene Moiety.,The Journal of Organic Chemistry

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Synthesis and Solid-State Dynamics of a Crystalline Steroid Molecular Rotor without the Alkyne Axle: Steroid Dimers Based on a 1,4-Di(1,3-dioxan-2-yl)benzene Moiety.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-06-01 , DOI: 10.1021/acs.joc.0c00867
Katherine Vargas-Romero ₁ , Fátima C Martínez-Torres ₁ , Andrés Aguilar-Granda ₂ , Salvador Pérez-Estrada ₃ , Marcos Flores-Alamo ₁ , Braulio Rodríguez-Molina ₂ , Martín A Iglesias-Arteaga ₁

Affiliation

Two diastereomeric crystalline steroid dimers were obtained by acid-catalyzed double acetalization of (20S)-5α-pregnan-3β,16β,20-triol 3-monoacetate with terephtalaldehyde. These compounds were characterized by NMR in solution, MS, single-crystal X-ray diffraction, and variable-temperature solid-state NMR by ¹³C cross-polarization magic angle spinning (CPMAS). While the phenylene rotator in the SR diastereomer remains static even at 373 K, the RR isomer shows a slow rotational process of the phenylene ring at temperatures above room temperature and thus may be considered the first crystalline steroid molecular rotor without the alkyne axle.

中文翻译：

没有炔烃轴的晶体甾体分子转子的合成和固态动力学：基于1,4-二（1,3-二恶烷-2-基）苯部分的甾体二聚体。

通过对苯二甲醛对（20S）-5α-pregnan-3β，16β，20-三醇3-单乙酸酯的酸催化双缩醛化反应获得了两个非对映体晶体甾体二聚体。这些化合物的特征在于溶液中的NMR，MS，单晶X射线衍射和¹³ C交叉极化幻角旋转（CPMAS）的可变温度固态NMR 。尽管SR非对映异构体中的亚苯基转子即使在373 K时仍保持静态，但RR异构体在高于室温的温度下显示了亚苯基环的缓慢旋转过程，因此可以认为是第一个没有炔烃轴的结晶类固醇分子转子。

更新日期：2020-07-02

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