Acid-catalyzed selective cyclization of 10,10-dibenzyl-9(10h)-anthranol
文献类型：期刊论文
| 作者 | Gao Chun-Mei; Cao De-Rong; Xu She-Yang |
| 刊名 | Acta chimica sinica
 |
| 出版日期 | 2006-08-28 |
| 卷号 | 64期号:16页码:1757-1760 |
| 关键词 | Anthranol Condensation Triptycene Electrophilic substitution |
| ISSN号 | 0567-7351 |
| 通讯作者 | Gao chun-mei() |
| 英文摘要 | Anthrone (1) reacted in pyridine/piperidine with 3,5-dimethoxybenzaldehyde (2) to give 10-(3,5-dimethoxybenzylidene)-9-anthrone (3). catalytic hydrogenation (5% pd on carbon) of 3 afforded 10-(3,5-dimethoxybenzyl)-9-anthrone (4). 10-(3,5-dimethoxybenzyl)-10-(3-methoxybenzyl)-9-anthrone (6) was obtained by alkylation of anthrone 4 with. 3-methoxybenzyl chloride (5). subsequent reduction of 6 with nabh4 gave 10-(3,5-dimethoxybenzyl)-10-(3-methoxybenzyl)-9(10h)-9-anthranol 7. 7 exhibits in the presence of formic acid or p-methylphenyl-sulfonic acid a selective 1,7-elimination of water which leads to homotriptycene (8). it could be assumed that the protonation of the hydroxy group leads to a carbenium ion intermediate which selectively attacks as electrophile the electron-rich benzene ring with 3,5-dimethoxy groups, instead of attacking the benzene ring with 3-methoxy group. |
| WOS关键词 | MODEL QUINONE METHIDES ; AGENTS ; ANTHRAHYDROQUINONE ; DERIVATIVES ; ANTHRANOL ; ADDUCTS |
| WOS研究方向 | Chemistry |
| WOS类目 | Chemistry, Multidisciplinary |
| 语种 | 英语 |
| WOS记录号 | WOS:000240294800026 |
| 出版者 | SCIENCE CHINA PRESS |
| URI标识 | http://www.irgrid.ac.cn/handle/1471x/2379436 |
| 专题 | 中国科学院大学 |
| 通讯作者 | Gao Chun-Mei |
| 作者单位 | 1.Chinese Acad Sci, Guangzhou Inst Chem, Key Lab Cellulose & Lignocellulosics Chem, Guangzhou 510650, Guangdong, Peoples R China 2.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China 3.S China Univ Technol, Coll Chem, Guangzhou 510640, Guangdong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Gao Chun-Mei,Cao De-Rong,Xu She-Yang. Acid-catalyzed selective cyclization of 10,10-dibenzyl-9(10h)-anthranol[J]. Acta chimica sinica,2006,64(16):1757-1760. |
| APA | Gao Chun-Mei,Cao De-Rong,&Xu She-Yang.(2006).Acid-catalyzed selective cyclization of 10,10-dibenzyl-9(10h)-anthranol.Acta chimica sinica,64(16),1757-1760. |
| MLA | Gao Chun-Mei,et al."Acid-catalyzed selective cyclization of 10,10-dibenzyl-9(10h)-anthranol".Acta chimica sinica 64.16(2006):1757-1760. |
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来源：中国科学院大学
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