6-(2-(3,3-二甲基噁丙环-2-基)乙基)
萘-1,4-二酮的合成

doi:10.3969/j.issn.1000-2006.2016.01.018

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南京林业大学学报（自然科学版） ›› 2016, Vol. 59 ›› Issue (01): 111-116.doi: 10.3969/j.issn.1000-2006.2016.01.018

6-(2-(3,3-二甲基噁丙环-2-基)乙基) 萘-1,4-二酮的合成

罗金岳¹,韩莉¹,陆强¹,柳华锋¹,刘祖广²

1.南京林业大学化学工程学院,江苏省生物质绿色燃料与化学品重点实验室,江苏南京 210037;
2.广西林产化学与工程重点实验室,广西南宁 530006

出版日期:2016-02-18 发布日期:2016-02-18
基金资助:
收稿日期:2015-01-26 修回日期:2015-07-13
基金项目:国家自然科学基金项目(31470597); 广西林产化学与工程重点实验室重点项目(GXFC13-01)
第一作者:罗金岳(luojinyue@njfu.com.cn),教授。
引文格式:罗金岳,韩莉,陆强,等. 6-(2-(3,3-二甲基噁丙环-2-基)乙基)萘-1,4-二酮的合成[J]. 南京林业大学学报(自然科学版),2016,40(1):111-116.

Synthesis of 6-(2-(3,3-dimethyloxiran-2-yl)ethyl)naphthalene-1,4-dione

LUO Jinyue¹,HAN Li¹,LU Qiang¹,LIU Huafeng¹,LIU Zuguang²

1. Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
2. Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530006, China

Online:2016-02-18 Published:2016-02-18

摘要/Abstract

摘要： 以6-(4-甲基-3-戊烯基)萘-1,4-二醌为原料,过氧乙酸为氧化剂,通过环氧化反应制备了目标产物6-(2-(3,3-二甲基噁丙环-2-基)乙基)萘-1,4-二酮。产物结构通过¹H-NMR、FT-IR和GC-MS分析得到表征和确定。探讨了反应底物、氧化剂以及碳酸氢钠的比例、溶剂、温度、时间等对反应转化率和得率的影响,得到优化工艺条件为:萘二醌、过氧乙酸和碳酸氢钠摩尔质量比为1:3:1.2,以氯仿为反应溶剂,反应温度30 ℃,反应时间5 h。在此优化条件下,可得到目标产物6-(2-(3,3-二甲基噁丙环-2-基)乙基)萘-1,4-二酮的得率为90.7%。

Abstract: An efficient and practical method for the synthesis of 6-(2-(3,3-dimethyloxiran-2-yl)ethyl)naphthalene-1,4-dione by utilizing epoxidation of 6-(4-methylpent-3-en-1-yl)naphthalene-1,4-dione withperacetic acid as an oxidant was described. The structure of the product was determined by ¹H-NMR, FT-IR and GC-MS analyses. Effects of solvent, reaction time, temperature and the ratio of the starting material, oxidant and sodium bicarbonate on conversion rate of the starting material and yield of the product were examined, and the optimal conditions were determined as follows: the molar ratio of 6-(4-methylpent-3-en-1-yl)naphthalene-1,4-dione/peracetic acid/sodium bicarbonate was 1:3:1.2,chloroform was used as the solvent, reaction temperature was 30 ℃, and reaction time was 5 h. The yield of 6-(2-(3,3-dimethyloxiran-2-yl)ethyl)naphthalene-1,4-dione reached 90.7% at aforesaid conditions.

中图分类号:

TQ254

罗金岳,韩莉,陆强,等. 6-(2-(3,3-二甲基噁丙环-2-基)乙基) 萘-1,4-二酮的合成[J]. 南京林业大学学报（自然科学版）, 2016, 59(01): 111-116.

LUO Jinyue,HAN Li,LU Qiang,LIU Huafeng,LIU Zuguang. Synthesis of 6-(2-(3,3-dimethyloxiran-2-yl)ethyl)naphthalene-1,4-dione[J].Journal of Nanjing Forestry University (Natural Science Edition), 2016, 59(01): 111-116.DOI: 10.3969/j.issn.1000-2006.2016.01.018.

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6-(2-(3,3-二甲基噁丙环-2-基)乙基) 萘-1,4-二酮的合成

Synthesis of 6-(2-(3,3-dimethyloxiran-2-yl)ethyl)naphthalene-1,4-dione

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