ε-己内酯合成6-溴己醇：合成特点及理论研究

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2025-05-15 DOI:10.1007/s11172-025-4595-5

A. D. Trubachev, K. V. Zaitsev

{"title":"ε-己内酯合成6-溴己醇：合成特点及理论研究","authors":"A. D. Trubachev, K. V. Zaitsev","doi":"10.1007/s11172-025-4595-5","DOIUrl":null,"url":null,"abstract":"<div>A three-steps procedure for obtaining 6-bromohexanol from available ε-caprolactone was modified to reach a total yield of 43%. Quantum chemistry methods were used to study a side process occurring in the second step of the synthesis, namely, the esterification of Br(CH2)5COOH with methanol which gives MeO(CH2)5COOMe, and a mechanism for the implementation of this step was proposed. Based on the suggested mechanism, the procedure for performing this step was corrected to avoid the side product formation.</div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 4","pages":"1007 - 1014"},"PeriodicalIF":1.7000,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of 6-bromohexanol from ε-caprolactone: synthetic features and theoretical aspects\",\"authors\":\"A. D. Trubachev, K. V. Zaitsev\",\"doi\":\"10.1007/s11172-025-4595-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>A three-steps procedure for obtaining 6-bromohexanol from available ε-caprolactone was modified to reach a total yield of 43%. Quantum chemistry methods were used to study a side process occurring in the second step of the synthesis, namely, the esterification of Br(CH2)5COOH with methanol which gives MeO(CH2)5COOMe, and a mechanism for the implementation of this step was proposed. Based on the suggested mechanism, the procedure for performing this step was corrected to avoid the side product formation.</div>\",\"PeriodicalId\":756,\"journal\":{\"name\":\"Russian Chemical Bulletin\",\"volume\":\"74 4\",\"pages\":\"1007 - 1014\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2025-05-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Chemical Bulletin\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11172-025-4595-5\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-025-4595-5","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: 0

摘要

对现有ε-己内酯制备6-溴己醇的三步法进行了改进，使总收率达到43%。利用量子化学方法研究了合成第二步中Br(CH2)5COOH与甲醇酯化反应生成MeO(CH2)5COOMe的副过程，并提出了该步骤的实现机理。基于建议的机制，执行这一步的程序被纠正以避免副产物的形成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Synthesis of 6-bromohexanol from ε-caprolactone: synthetic features and theoretical aspects

A three-steps procedure for obtaining 6-bromohexanol from available ε-caprolactone was modified to reach a total yield of 43%. Quantum chemistry methods were used to study a side process occurring in the second step of the synthesis, namely, the esterification of Br(CH₂)₅COOH with methanol which gives MeO(CH₂)₅COOMe, and a mechanism for the implementation of this step was proposed. Based on the suggested mechanism, the procedure for performing this step was corrected to avoid the side product formation.

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

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.