一种微波辅助高效还原合成烷基取代[2.2]-副环番烷的方法

Mengyuan Tian, Lixiang Zhang, Lijing Gao, G. Xiao
{"title":"一种微波辅助高效还原合成烷基取代[2.2]-副环番烷的方法","authors":"Mengyuan Tian, Lixiang Zhang, Lijing Gao, G. Xiao","doi":"10.1177/17475198231164370","DOIUrl":null,"url":null,"abstract":"[2.2]-Paracyclophane derivatives have been promising platforms for applications in biology and materials science. To access pure derivatives thereof, a safe and non-toxic synthetic method for 4-n-propyl-[2.2]-paracyclophane is developed via a microwave-assisted and NH2NH2/KOH reduction route. We introduce microwave-assisted acylation for a synthesis that successfully improves the yield and reduces the reaction time. Notably, an exploration of the length and number of the alkyl chains on the [2.2]-paracyclophane ring did not significantly affect the outcome of this reaction. We synthesized 4-n-butyl-[2.2]-paracyclophane and 4,12-dipropyl-[2.2]-paracyclophane via our protocol with high yields. The regioselectivity of the second electrophilic substitution on 4-n-propyl-[2.2]-paracyclophane occurs at the para position of the less substituted phenyl ring.","PeriodicalId":15318,"journal":{"name":"Journal of Chemical Research-s","volume":"77 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2023-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A microwave-assisted and efficient reduction protocol for the synthesis of alkyl-substituted [2.2]-paracyclophanes\",\"authors\":\"Mengyuan Tian, Lixiang Zhang, Lijing Gao, G. Xiao\",\"doi\":\"10.1177/17475198231164370\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"[2.2]-Paracyclophane derivatives have been promising platforms for applications in biology and materials science. To access pure derivatives thereof, a safe and non-toxic synthetic method for 4-n-propyl-[2.2]-paracyclophane is developed via a microwave-assisted and NH2NH2/KOH reduction route. We introduce microwave-assisted acylation for a synthesis that successfully improves the yield and reduces the reaction time. Notably, an exploration of the length and number of the alkyl chains on the [2.2]-paracyclophane ring did not significantly affect the outcome of this reaction. We synthesized 4-n-butyl-[2.2]-paracyclophane and 4,12-dipropyl-[2.2]-paracyclophane via our protocol with high yields. The regioselectivity of the second electrophilic substitution on 4-n-propyl-[2.2]-paracyclophane occurs at the para position of the less substituted phenyl ring.\",\"PeriodicalId\":15318,\"journal\":{\"name\":\"Journal of Chemical Research-s\",\"volume\":\"77 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-03-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Chemical Research-s\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1177/17475198231164370\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Research-s","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1177/17475198231164370","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

摘要

[2.2]-副环烷衍生物在生物和材料科学领域的应用前景广阔。为了获得其纯衍生物,通过微波辅助和NH2NH2/KOH还原路线,开发了一种安全无毒的4-n-丙基-[2.2]-副环环烷合成方法。我们引入微波辅助酰化合成,成功地提高了产率,缩短了反应时间。值得注意的是,对[2.2]-副环环烷环上烷基链的长度和数量的探索并没有显著影响该反应的结果。我们以较高的收率合成了4-正丁基-[2.2]-对环己烷和4,12-二丙基-[2.2]-对环己烷。4-n-丙基-[2.2]-对环己烷第二次亲电取代的区域选择性发生在取代较少的苯基环的对位上。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
A microwave-assisted and efficient reduction protocol for the synthesis of alkyl-substituted [2.2]-paracyclophanes
[2.2]-Paracyclophane derivatives have been promising platforms for applications in biology and materials science. To access pure derivatives thereof, a safe and non-toxic synthetic method for 4-n-propyl-[2.2]-paracyclophane is developed via a microwave-assisted and NH2NH2/KOH reduction route. We introduce microwave-assisted acylation for a synthesis that successfully improves the yield and reduces the reaction time. Notably, an exploration of the length and number of the alkyl chains on the [2.2]-paracyclophane ring did not significantly affect the outcome of this reaction. We synthesized 4-n-butyl-[2.2]-paracyclophane and 4,12-dipropyl-[2.2]-paracyclophane via our protocol with high yields. The regioselectivity of the second electrophilic substitution on 4-n-propyl-[2.2]-paracyclophane occurs at the para position of the less substituted phenyl ring.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Journal of Chemical Research-s
Journal of Chemical Research-s 化学科学, 有机化学, 有机合成
自引率
0.00%
发文量
0
审稿时长
1 months
期刊介绍: The Journal of Chemical Research is a peer reviewed journal that publishes full-length review and research papers in all branches of experimental chemistry. The journal fills a niche by also publishing short papers, a format which favours particular types of work, e.g. the scope of new reagents or methodology, and the elucidation of the structure of novel compounds. Though welcome, short papers should not result in fragmentation of publication, they should describe a completed piece of work. The Journal is not intended as a vehicle for preliminary publications. The work must meet all the normal criteria for acceptance as regards scientific standards. Papers that contain extensive biological results or material relating to other areas of science may be diverted to more appropriate specialist journals. Areas of coverage include: Organic Chemistry; Inorganic Chemistry; Materials Chemistry; Crystallography; Computational Chemistry.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信