Synthesis of Bicyclo[3.3.1]nonane-2,6,9-trione

doi:10.6023/cjoc201309009

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (2): 376-381.DOI: 10.6023/cjoc201309009 Previous Articles Next Articles

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双环[3.3.1]壬烷-2,6,9-三酮的合成

任晓莉, 凌亦飞, 罗军

南京理工大学化工学院南京 210094

收稿日期:2013-09-06 修回日期:2013-10-22 发布日期:2013-10-25
通讯作者: 罗军 E-mail:luojun@njust.edu.cn

Synthesis of Bicyclo[3.3.1]nonane-2,6,9-trione

Ren Xiaoli, Ling Yifei, Luo Jun

School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094

Received:2013-09-06 Revised:2013-10-22 Published:2013-10-25

1. Synthesis of Bicyclo[3.3.1]nonane-2,6,9-trione.PDF(717KB)

Abstract

A novel compound bicyclo[3.3.1]nonane-2,6,9-trione was synthesized from cyclohexane-1,3-dione through three routes and some reaction mechanisms were proposed. The first route afforded bicyclo[3.3.1]nonane-2,6,9-trione in a total yield of 43% via Michael addition with cyclohexane-1,3-dione and acrolein, intermolecular Aldol condensation and oxidation. The second route gave target product in 20% yield via a one-pot process including formation of enamine with morpholine and cyclization with acrylic ethyl ester. The third route also used cyclohexane-1,3-dione and acrylic ethyl ester as start materials and resulted bicyclo[3.3.1]nonane-2,6,9-trione with a high total yield of 83% via Michael addition and intermolecular C-acylation. This process has the advantages of simple operation, mild reaction conditions, high yield and environmental friendship.

Key words: cyclohexane-1,3-dione, bicyclo[3.3.1]nonane-2,6,9-trione, acrolein, acrylic ethyl ester, cyclization

Cite this article

Ren Xiaoli, Ling Yifei, Luo Jun. Synthesis of Bicyclo[3.3.1]nonane-2,6,9-trione[J]. Chin. J. Org. Chem., 2014, 34(2): 376-381.

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双环[3.3.1]壬烷-2,6,9-三酮的合成

Synthesis of Bicyclo[3.3.1]nonane-2,6,9-trione

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