Synthesis of new heterocyclic resveratrol analogues in milli- and microreactors: intensification of the Wittig reaction

IF 2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Flow Chemistry Pub Date : 2022-08-05 DOI:10.1007/s41981-022-00239-9
Milena Mlakić, Lucija Rajič, Anabela Ljubić, Vitomir Vušak, Bruno Zelić, Martin Gojun, Ilijana Odak, Ivona Čule, Ivana Šagud, Anita Šalić, Irena Škorić
{"title":"Synthesis of new heterocyclic resveratrol analogues in milli- and microreactors: intensification of the Wittig reaction","authors":"Milena Mlakić,&nbsp;Lucija Rajič,&nbsp;Anabela Ljubić,&nbsp;Vitomir Vušak,&nbsp;Bruno Zelić,&nbsp;Martin Gojun,&nbsp;Ilijana Odak,&nbsp;Ivona Čule,&nbsp;Ivana Šagud,&nbsp;Anita Šalić,&nbsp;Irena Škorić","doi":"10.1007/s41981-022-00239-9","DOIUrl":null,"url":null,"abstract":"<div><p>Resveratrol is a natural bioactive non-flavonoid polyphenol that protects from cardiovascular disease, neurodegenerative diseases and various cancers. Unfortunately, the amounts of resveratrol in plants are low and therefore, chemical synthesis is still the main way to obtain this valuable structure. In this work, Wittig reaction was chosen as the synthetic route for the study on technology influence in batch vs. micro- or milliflow reactors during the production of new resveratrol-like compounds. A series of reactions was carried out by batch synthesis, and intensified in a milli- and a microreactor, changing the reaction conditions to increase the efficiency and productivity of the process. Results were compared based on conversion, yield, productivity and <i>trans/cis</i> ratio. Similar yields and conversions were obtained in all reaction systems, but in much shorter time in the milli- and microscale compared to the batch reactor. On the other hand, higher productivities were obtained in the millireactor and microreactor, making them better systems for the proposed reactions of new heterocyclic resveratrol analogues synthesis.</p><h3>Graphical abstract</h3>\n <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\n </div>","PeriodicalId":630,"journal":{"name":"Journal of Flow Chemistry","volume":"12 4","pages":"429 - 440"},"PeriodicalIF":2.0000,"publicationDate":"2022-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"5","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Flow Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s41981-022-00239-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 5

Abstract

Resveratrol is a natural bioactive non-flavonoid polyphenol that protects from cardiovascular disease, neurodegenerative diseases and various cancers. Unfortunately, the amounts of resveratrol in plants are low and therefore, chemical synthesis is still the main way to obtain this valuable structure. In this work, Wittig reaction was chosen as the synthetic route for the study on technology influence in batch vs. micro- or milliflow reactors during the production of new resveratrol-like compounds. A series of reactions was carried out by batch synthesis, and intensified in a milli- and a microreactor, changing the reaction conditions to increase the efficiency and productivity of the process. Results were compared based on conversion, yield, productivity and trans/cis ratio. Similar yields and conversions were obtained in all reaction systems, but in much shorter time in the milli- and microscale compared to the batch reactor. On the other hand, higher productivities were obtained in the millireactor and microreactor, making them better systems for the proposed reactions of new heterocyclic resveratrol analogues synthesis.

Graphical abstract

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
在微反应器和微反应器中合成新的杂环白藜芦醇类似物:强化Wittig反应
白藜芦醇是一种天然的生物活性非类黄酮多酚,可预防心血管疾病、神经退行性疾病和各种癌症。不幸的是,植物中白藜芦醇的含量很低,因此,化学合成仍然是获得这种有价值结构的主要方法。本文选择Wittig反应作为合成路线,研究了间歇反应器与微、毫流反应器生产新型白藜芦醇类化合物的工艺影响。通过间歇式合成进行了一系列反应,并在微反应器和微反应器中进行了强化,改变了反应条件,提高了反应的效率和生产率。结果根据转化率、产量、生产率和反顺比进行比较。在所有的反应系统中都获得了相似的产率和转化率,但在毫微米尺度上与间歇式反应器相比所需的时间要短得多。另一方面,微反应器和微反应器的反应效率较高,是合成新型杂环白藜芦醇类似物的较好系统。图形抽象
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Journal of Flow Chemistry
Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
6.40
自引率
3.70%
发文量
29
审稿时长
>12 weeks
期刊介绍: The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.
期刊最新文献
Rapid and practical synthesis of N-protected amino ketones in continuous flow via pre-deprotonation protocol Expedited access to β-lactams via a telescoped three-component Staudinger reaction in flow Efficient “One-Column” grignard generation and reaction in continuous flow Two deep learning methods in comparison to characterize droplet sizes in emulsification flow processes Enhanced emulsification process between viscous liquids in an ultrasonic capillary microreactor: mechanism analysis and application in nano-emulsion preparation
×
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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1