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Control of Guest Inclusion and Chiral Recognition Ability of 6-O-Modified β-Cyclodextrins in Organic Solvents by Aromatic Substituents at the 2-O Position.
ChemPlusChem ( IF 3.0 ) Pub Date : 2020-08-10 , DOI: 10.1002/cplu.202000522
Justine M Kalaw 1 , Ryusuke Yamamoto 1 , Chizuru Kogame-Asahara 1 , Hajime Shigemitsu 1 , Toshiyuki Kida 1
Affiliation  

The host‐guest chemistry and applications of cyclodextrins in aqueous media is well established. However, a comprehensive study in organic solvents is lacking. Here, we report the design and synthesis of 6‐Otert‐butyldimethylsilylated β‐cyclodextrin (TBDMS‐β‐CD) bearing various aromatic substitutions at the 2‐O position and their inclusion complex formation with aromatic guests in nonpolar organic solvents. Compared to the parent TBDMS‐β‐CD, these derivatives exhibit at least a 10‐fold increase in inclusion ability toward pyrene through cooperative guest binding with the CD cavity and the aromatic substituents at the 2‐O position. The type of the aromatic substituent largely affects the chiral recognition ability of TBDMS‐β‐CD toward 1‐(1‐naphthyl)ethylamine in cyclohexane. A TBDMS‐β‐CD derivative with a p‐tolyl substituent has a remarkable chiral selectivity for the (S)‐1‐(1‐naphthyl)ethylamine over the corresponding (R)‐isomer (KS/KR=4.1±0.5), whereas a TBDMS‐β‐CD derivative with a 2‐picolyl substituent shows the inverse chiral selectivity (KR/KS=8.7±0.6).

中文翻译:

通过2-O位置的芳族取代基控制有机溶剂中6-O修饰的β-环糊精的客体包涵体和手性识别能力。

环糊精在水性介质中的客体化学性质和应用已得到公认。但是,缺乏对有机溶剂的全面研究。这里,我们报告的6-设计和合成ö --butyldimethylsilylatedβ环糊精(TBDMS-β-CD)在2-轴承各种芳族取代ö位置和它们的包合配合物的形成与在非极性有机溶剂的芳族的客人。与母体TBDMS-β-CD相比,这些衍生物通过与CD腔和2- O处的芳族取代基的协同客体结合,对pyr的包合能力至少提高了10倍位置。芳族取代基的类型在很大程度上影响TBDMS-β-CD在环己烷中对1-(1-萘基)乙胺的手性识别能力。具有甲苯基取代基的TBDMS-β-CD衍生物对(S)-1-(1-萘基)乙胺的手性相对于相应的(R)-异构体具有显着的手性选择性(K S / K R = 4.1±0.5 ),而带有2-picolyl取代基的TBDMS-β-CD衍生物则表现出相反的手性选择性(K R / K S = 8.7±0.6)。
更新日期:2020-08-28
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