2,6-二氧杂双环[3.2.1]辛烷类衍生物的串联合成

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (3): 514.

2,6-二氧杂双环[3.2.1]辛烷类衍生物的串联合成

金慧娟^1,2, 鲁静¹, 郑宁娟¹, 吴学^1,2

1. 延边大学化学系,
2. 延边大学长白山生物资源与功能分子教育部重点实验室, 延吉 133002

收稿日期:2009-03-04 出版日期:2010-03-10 发布日期:2010-03-10
通讯作者: 金慧娟, 女, 博士, 副教授, 主要从事有机合成研究. E-mail: jinhj@ybu.edu.cn
基金资助:
延边大学长白山生物资源与功能分子教育部重点实验室课题基金(批准号: 2009-2011)资助.

Tandem Synthesis of 1,3-Disubstituted 2,6-Dioxabicylco-[3.2.1]Octane Derivatives

JIN Hui-Juan^1,2*, LU Jing¹, ZHENG Ning-Juan¹, WU Xue^1,2

1. Department of Chemistry, Yanbian University,
2. Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules, Ministry of Education, Yanbian University, Yanji 133002, China

Received:2009-03-04 Online:2010-03-10 Published:2010-03-10
Contact: JIN Hui-Juan. E-mail: jinhj@ybu.edu.cn
Supported by:
延边大学长白山生物资源与功能分子教育部重点实验室课题基金(批准号: 2009-2011)资助.

摘要/Abstract

摘要：

以2-甲基-4-戊烯-1,2-二醇和芳香醛为原料, 三氯化铟为催化剂, 得到了一系列1,3-二取代2,6-二氧杂双环[3.2.1]辛烷类衍生物. 整个反应采用一锅法, 反应条件简单且产率高. 所有的化合物均用¹H NMR, ¹³C NMR和质谱法进行了表征, 并用NOESY确立了分子的相对构型.

关键词: Prins 环化反应; 二氧杂双环[3.2.1]辛烷; 一锅合成

Abstract:

A series of 1,3-disubstituted 2,6-dioxabicyclo[3.2.1]octane derivatives were obtained by a tandem reaction of 2-methyl-4-penten-1,2-diol and various aromatic aldehydes catalyzed by indium trichloride in high yields. These products were generated through sequential acetalization, Prins cyclization and intramolecular nucleophilic addition reactions in one pot. All of the new compounds were confirmed via ¹H NMR, ¹³C NMR and MS analysis, and the configuration of product was determined by the NOESY experiment.

Key words: Prins cyclization; Dioxabicyclo[3.2.1]octane; One-pot synthesis

TrendMD:

金慧娟, 鲁静, 郑宁娟, 吴学. 2,6-二氧杂双环[3.2.1]辛烷类衍生物的串联合成. 高等学校化学学报, 2010, 31(3): 514.

JIN Hui-Juan*, LU Jing, ZHENG Ning-Juan, WU Xue. Tandem Synthesis of 1,3-Disubstituted 2,6-Dioxabicylco-[3.2.1]Octane Derivatives. Chem. J. Chinese Universities, 2010, 31(3): 514.

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