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三联并苯笼状化合物：具有六个[5]并苯单元的三维π共轭手性笼状化合物。

Triple Helicene Cage: Three-Dimensional π-Conjugated Chiral Cage with Six [5]Helicene Units.

作者信息

Matsushima Tomoya, Kikkawa Shoko, Azumaya Isao, Watanabe Soichiro

机构信息

Department of Biomolecular Science, Faculty of Science and Research Center for, Materials with Integrated Properties Toho University Miyama 2-2-1, Funabashi Chiba 274-8510 Japan.

Faculty of Pharmaceutical Sciences Toho University Miyama 2-2-1, Funabashi Chiba 274-8510 Japan.

出版信息

ChemistryOpen. 2018 Feb 16;7(4):278-281. doi: 10.1002/open.201800006. eCollection 2018 Apr.

DOI:10.1002/open.201800006
PMID:29657913
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5891663/
Abstract

A three-dimensional π-conjugated chiral cage with six [5]helicene units (a triple helicene cage) was synthesized for the first time. Taking advantage of the Yamamoto coupling reaction, the triflate-substituted triple [5]helicene, a strained and preorganized precursor, was dimerized to afford the target compound. Single-crystal X-ray diffraction analysis revealed the unique structural features of the triple helicene cage: a cage-shaped rigid structure with outer helical grooves and an inner chiral cavity. All- and all- enantiomers were separated successfully by HPLC over a chiral column and their chiroptical properties were characterized by circular dichroism spectra.

摘要

首次合成了一种具有六个[5]螺旋烯单元的三维π共轭手性笼（三螺旋烯笼）。利用山本偶联反应，将三氟甲磺酸酯取代的三[5]螺旋烯（一种张力预组织前体）二聚化，得到目标化合物。单晶X射线衍射分析揭示了三螺旋烯笼的独特结构特征：具有外部螺旋槽和内部手性腔的笼状刚性结构。通过高效液相色谱在手性柱上成功分离了全同和全对映体，并通过圆二色光谱对其手性光学性质进行了表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/20d06d9764da/OPEN-7-278-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/0a56c469aac2/OPEN-7-278-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/78e2446a399d/OPEN-7-278-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/be93e9817515/OPEN-7-278-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/8c14abbc341c/OPEN-7-278-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/f26f640a92eb/OPEN-7-278-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/20d06d9764da/OPEN-7-278-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/0a56c469aac2/OPEN-7-278-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/78e2446a399d/OPEN-7-278-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/be93e9817515/OPEN-7-278-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/8c14abbc341c/OPEN-7-278-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/f26f640a92eb/OPEN-7-278-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/57dd/5891663/20d06d9764da/OPEN-7-278-g005.jpg

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