Iptycene quinones: synthesis and structure.
Iptycene quinones: synthesis and structure.
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DOI：
10.1021/jo0483015
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发表时间：
2005-02
期刊：
影响因子：
--
通讯作者：
Xiao-Zhang Zhu;Chuan-feng Chen
中科院分区：
文献类型：
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作者：
Xiao-Zhang Zhu;Chuan-feng Chen
本文介绍了一种实用、有效的合成异蝶烯醌类化合物的方法。结果表明，三蝶烯醌4或5与蒽1或其衍生物2-3在四氯对苯醌存在下，于冰醋酸中一锅反应，再经CAN氧化脱甲基，可方便地合成一系列五蝶烯醌8-16。类似地，用五蝶烯醌10和三蝶烯二醌6作为前体，获得了一系列具有U形空腔的七蝶烯醌17-23。以蒽和五蝶烯醌16 a、16 b为原料，通过一锅法合成了具有一个镊子形空腔的非蝶烯醌24和具有两个U形空腔的非蝶烯醌25。通过蒽与五蝶烯二醌12或三蝶烯三醌7的反应，方便地获得具有树枝状结构的非蝶烯三醌26。区域异构体16 a和16 b的结构通过16 b的单晶结构分析确定。其他区域异构体，包括庚蝶烯萘醌19 a/19 b/19 c和庚蝶烯萘醌23 a/23 b的结构通过比较反应进行了鉴定。
A practical and efficient method to synthesize iptycene quinones has been developed. As a result, a series of pentiptycene quinones 8-16 were conveniently synthesized by one-pot reaction of triptycene quinone 4 or 5 with anthracene 1 or its derivatives 2-3 in refluxing acetic acid in the presence of p-chloranil, followed by CAN oxidative demethylation. Similarly, a series of heptiptycene quinones 17-23 with U-shaped cavities were achieved with pentiptycene quinone 10 and triptycene diquinone 6 as precursors. Non-iptycene triquinones 24 with one tweezer-shaped cavity and 25 with two U-shaped cavities were synthesized by one-pot reactions of anthracene with pentiptycene triquinones 16a and 16b, respectively. Non-iptycene triquinone 26 with a dendritic structure was conveniently obtained by the reaction of anthracene with either pentiptycene diquinone 12 or triptycene triquinone 7. The structures of regioisomers 16a and 16b were determined by the single-crystal structure analysis of 16b. The structures of other regioisomers, including heptiptycene tetraquinones 19a/19b/19c and heptiptycene triquinones 23a/23b, were identified by comparative reactions.